Big Daddy Homie

THIS IS A WORK OF FICTION!! There is nothing about this post that is even remotely true. It is a "fictional autobiography," if you will, and I only wrote it because I thought it would be a cool subject to explore and write about, as if I had lived it myself.

CHAPTER 1: LIFE BEFORE THE BIG WIN

To understand how I so dramatically burned through several millions of dollars, and how in doing so I lost everything else that was important in my life, it helps to know a little bit about who I was before my big win, and about the events leading up to it.

Again, let me apologize for being oblique and secretive, but I want to protect my anonymity.

I was born in 1970, in a medium-sized Midwestern city. I was the first child of both my mother and my father, and their marriage to each other was the first for either of them. They divorced when I was in pre-school, and I have only hazy memories of them being together. After their divorce, mom and I bounced around between cheap apartments and stays with my grandparents or other relatives, until my mom married my stepfather, a few months after I started Kindergarten. My stepfather had two kids from a previous marriage, a girl who was three years older than me and a boy who was about fourteen months older than me. A few months after the wedding, my half-brother was born.

My upbringing was probably along the lines of lower middle class, though it never seemed that way. We never wanted for food or material goods, and we vacationed pretty regularly. But we lived in an urban neighborhood that was in its decline, and a lot of our school clothes came from thrift stores. This was in the days before shopping at thrift stores became cool; in my day, being seen going into or out of a thrift store was instant social suicide.

The house we lived in was a three-bedroom bungalow that had seen better days. The house had one upstairs bathroom, and a sink & toilet in the partially-furnished basement (which I was afraid to go down into). My mother, stepfather, half-brother and I shared that one bathroom, and when my stepbrother & stepsister were in town every other weekend, there were even more people in the mix. My stepfather gained full custody of his kids when I was 11, which means that, for the better part of seven years, six people shared one functional bathroom.

Nevertheless, my stepfather was handy, and so for all its limitations our house never leaked, had drafts, or faced any of the other ills that plague decaying urban houses. My stepfather did his best to make sure that we had enough comfortable bedrooms for all of us, even if that meant one of us boys having a bedroom in the basement (fortunately, it wasn’t me!).

Our backyard was a ragtag postage stamp of a yard up against an alley. A privacy fence was put around it at some point, but it was always too hot or too cold to play outside, so we spent precious little time out there. For all his skills with tools, my stepfather couldn’t landscape to save his life, and the yard remained a bare patch of earth that we kids pretty much ignored for our entire childhoods.

We lived on a corner with a stop sign, and I remember that my mother would get livid when people would drop their trash out of their cars when they stopped at our intersection (which was pretty often). Across the street from us, to the north, was a bare expanse of paved concrete, next to an office/warehouse of some kind, and we kids would often play on that surface when it wasn’t covered with railroad ties. On the block to the north of our house, one side of the street was all offices and warehouses, one of which burned down when I was eleven and sits abandoned to this day.

To my parents, money was simply a tool to be used or misused as need be. My mother (who, for the most part, handled the checkbook), was a master of manipulating money. She could juggle three checking accounts, transferring nonexistent money from one to another (by writing rubber checks) and more than once rushing to the bank to deposit her paycheck in order to cover a check she had written – a practice that, I presume, continues to this day. She would pay bills based on whichever account had the most money in it, and when she overdrew one account she would simply move money into it from another account, even if there was no money to move. Mom seemed to know pretty much to the minute when her bills would be overdue, and most of them seemed to be paid right up against the deadline. She also seemed to know down to the minute how much time she had before a check drawn on one bank would clear at the other bank, and there were more than a few eleventh-hour trips to a bank in my childhood. After I had gotten my driver’s license and could drive, Mom would sometimes have me do her last-minute banking for her after school.

Both my parents made good salaries, but yet there was never enough money. Mom could spend it as fast as she made it, and usually faster. I remember my stepfather desperately wanted a garage, but there was never enough money and so all of our families’ cars were parked on the street, which meant that slashed tires and broken windows were pretty much yearly occurrences. Nevertheless, we never did without on things that really mattered, and we took several weekend trips to area theme parks and the like, and a nice summer vacation to the Smoky Mountains every year.

When I was seven, we took a vacation that would change my life forever. Walt Disney World had opened a few years earlier, and my grandparents and parents had been talking about taking us kids for a couple of years. One summer, they stopped talking about it and actually did it. I remember four kids and two adults cramming into a van with no air conditioning, with my grandparents trailing behind us in their own car. The plan was to first stop in Jacksonville (Florida), so we kids could see the ocean and my grandfather could visit with his brother who lived there.

For weeks leading up to the trip, my parents and grandparents talked up the idea of seeing the ocean, almost as much as they talked up going to Disneyworld. I was as excited about seeing the ocean as I was about seeing Mickey. I remember my grandfather teasing me about how salty the ocean was, and daring me to stick my finger in it and then lick my finger. Even at that young age, I wasn’t afraid of a dare, so I told him I’d do it!

We arrived in Jacksonville after three long days of frequent pit stops and incessant cries of “Are we there yet?” We found a relatively secluded stretch of ocean, and my stepfather parked the van. All of us kids made a mad dash for the water. I ran in to waist-deep water and, remembering my grandfather’s dare, stuck my fingers in and then licked one. As expected, it tasted horrible! But at least Grandpa couldn’t say I didn’t try it.

My first experience with the ocean brought a host of emotions that I hadn’t expected. The power of the waves of awesome – they literally picked me up and threw me back to the shore. The foam would bubble and fizz around my body while seaweed licked up against me. The advancing and retreating waves made patterns on the beach that I found fascinating. And as I looked out on the vast expanse of sea, being vaguely aware that Africa was on the other side, I wondered what was going on over there: were kids my age looking across the ocean, wondering what was going on in Florida? I sat on the sand and let the warm waves wash over me. I was hooked.

Over the next several years my family would make numerous trips to Florida, mostly for Disneyworld, but occasionally stopping at the beach (we found Daytona Beach more to our liking than Jacksonville). The lush vegetation and palm trees were a welcome relief from the flat farmland of the Midwest. And when we went in the colder months, the warm weather and sunshine brought relief from the brutal cold back home. I had a pretty firm idea, by age 12, that I was going to get out of the Midwest and head south at the first chance I got.

Speaking of brutal cold, one of the things that cultivated my hatred of my childhood and of the Midwest was winter. Where I lived, the sun would set at around 4:30 on the shortest winter days. This meant that in high school, on days when my mom would make me do her banking, it would be dark by the time I got home from school, I hated it. And the cold was unbearable; I remember, in college, there was a stretch one December where, for three solid weeks, the temperature never got above zero. To me, winter represented a four-month period where life essentially came to a screeching halt, and actually enjoying life took a back seat to merely surviving.

Another event that changed my life happened at around age 11 or 12. The jackpot in the Illinois lottery reached a record $40 million. Today, lottery jackpots regularly climb well over sixty or seventy million, and sometimes reach into the hundreds of millions, but in 1981 state lotteries were a relatively new thing and this kind of money was big news. $40 million was a lot more money in 1981 than it was in 2002. And keep in mind that this was in the era before multi-state lotteries like Powerball and Mega Millions made $40-million-plus lottery jackpots commonplace.

The record-breaking jackpot made national headlines. At the time, state lottery payouts were usually in the range of four to six million, but several weeks of successive rollover jackpots head propelled Illinois’ jackpot into headline-worthy numbers. People from outside of Illinois would drive into the state to buy tickets. And, needless to say, everybody in America was talking about what they would do with $40 million. And I, as a pubescent kid, had some pretty firm ideas of what I would do with the money, too, even though I was too young to buy a ticket. Those plans involved a mansion on the beach in Florida, high-dollar sports cars (never mind that I was too young to drive), and a room full of Star Wars toys.

The jackpot was won by a Chicago-area man by the name of Michael Wittkowski (I may be spelling his name wrong). I remembered seeing him on the news. He was a regular, blue-collar guy. He spoke of plans to open a nautical-themed bar or restaurant (if I remember correctly). And of course he was going to pay off all of his bills, buy his wife a new car, and all that good stuff. At the time, there was no way to claim a “cash option” on the jackpot, so he would have to take an annuity.

On most (if not all) state lotteries, winners now have the option of taking the “cash option” on the jackpot. What this means is that they can take a lump-sum payment of one-half the advertised jackpot. The other option is to take the full amount of the advertised jackpot in annuity payments, spread out over twenty (or sometimes more) years. For example, if the advertised jackpot is $50 million, the winner can either take $25 million up front, or take $2.5 million per year over twenty years (2.5 X 20 = 50).

Most lottery winners take the cash option (that’s what I did), preferring to have the money up front. A handful take the annuity option. In the Michael Wittkowski era, taking the cash value wasn’t an option, which means that Mr. Wittkowski got $2 million per year for twenty years. That twenty-year period would have ended around 2001 or 2002, so that means that as of this writing Michael Wittkowski has been on his own for five years or so. I wonder sometimes if he invested well and is living the good life, or if he’s divorced and broke like me.

By age 12 I had caught lottery fever. Before the age of 18, I would sometimes give my mom some money and ask her to buy me a ticket, and we’d spend couple of days speculating about what we’d do with the money. Once I turned 18, I could, of course, buy lottery tickets legally, and I would do so in spades. By the time I reached my middle twenties, I was buying tickets in $5 batches more or less twice per week. I figured that my five-dollar investment bought me a few hours of shameless daydreaming, so it was worth it.

By the time I was ready to go to college I was pretty desperate to get out of the house. My stepbrother was quite the ladies’ man, and the phone in our house rang incessantly with girls trying desperately to get a few seconds of his attention. The phone also rang off the wall with bill collectors calling for my parents, who would ask me to lie for them and tell them they were out – of course, the bill collectors would want better explanations, and I was on the spot, so sometimes I’d just hang up, and my mother would lecture me for being rude.

Our house was basically a madhouse at this time. There was the one bathroom shared by five people; the phone ringing off the hook; my stepbrothers’ girlfriends coming and going; my half-brother getting into trouble and getting into yelling matches with my mother at every opportunity. The neighborhood that we lived in, which was in the very beginning stages of decline when we moved there (when I was four), was now full-tilt on its way to becoming a ghetto. Our family’s cars were vandalized or broken into pretty regularly, and I wondered when we were going to be robbed. I wanted so desperately to get out of that house that every single day I spent there was a nightmare.

Then there were the military recruiters. Somehow our local Army recruiters decided that the Army was just the thing for me, despite the fact that I had long hair, a bad attitude in the extreme, and I couldn’t run a block without getting winded. Nevertheless, they were there twice a week, extolling the virtues of the Army despite my utter lack of interest. One night I got sick of it and asked the recruiter point black if I was really the type of person the Army thought they needed. I reminded him that I had a bad attitude, I hated authority, I wasn’t by anybody’s definition in shape, and I had absolutely no goals of any kind. He mentioned some nonsense about being all I could be, the Army helping me fulfill my maximum potential, blah blah blah. I would have shown him the door, but I was afraid of him, so I simply got up from the table, walked to my room, and locked the door. I later heard from my mom (while she was lecturing me about rudeness) that the poor recruiter sat there at the table looking confused for a few minutes, and then got up and left. I’m sorry to say that it wasn’t the last I heard from the Army.

My parents hadn’t saved so much as one thin dime for any kind of college fund for us kids. My stepsister was pregnant and married before graduating high school, so college wasn’t a concern for her. My stepbrother was a star football player and had a half-ride scholarship to some obscure little college in northern Illinois. Paying for college wasn’t a concern for my half-brother, since we all knew that he was going to have a job with his name sewn on his shirt. That left my parents scrambling to find a way to pay for me to go to college, and to make up the difference in my stepbrother’s college costs.

We attended seminars on grants and such. My parents made too much money (!) to qualify for any kind of grants. Scholarships were out: I was a terrible student, and I thought high school was far too beneath me for me to do anything so condescending as homework. I did just enough work to get by and managed to graduate with a “C” average – enough to get into college, but not enough for any kind of scholarships. My parents pushed hard for the military, but I was having none of it. Mom mentioned me living at home and going to community college. I told her I’d die first. The only other option was to take out student loans.

I had wanted to go to college in Florida. The cost of out-of-state tuition put that dream to rest pretty quickly – there was only so much money available in student loans, and definitely not enough to cover out-of-state tuition. I wound up enrolling in a nearby state university that was close enough to home to be available for weekend visits, but far enough away that I was free of the madness that was my childhood home. My dream of going to Florida at the first chance I got had died, but I was so glad to be out of the house that it didn’t matter.

I did pretty well my first year in college. I had asked for, and gotten, a room on a 24-hour quiet floor in my dorm, and I ate it up. Gone were the constant yelling, the constant phone calls, and the constant in-and-out that was the background at home. If I wanted peace and quiet, I had it in spades. And if I was bored and needing something to do, there was always a party, or a discussion group, a game of chess, or some other thing to be involved in, and I found it quite to my liking. There was also classwork, and since I was in my element and no longer in high school, I got pretty good grades. I missed the Dean’s List by a quarter of a point my first semester.

Things went sour my second year. I had found a girlfriend in my second semester of my first year, named Crystal, and our relationship was pretty torrid. We’d study together, go to parties together, or try to sneak some quiet sex when her roommate was asleep. As the semester ended, we both knew we wanted to continue our relationship. We knew it would be hard over the summer, since we lived at different ends of the state, but we’d give it a try.

Over the summer we made frequent phone calls to each other, pledging our undying love and going on about how much we missed each other. By August, however, her tone had sharpened a little bit, and she seemed less interested in talking to me. When the fall semester of our second year began, she didn’t turn up in my room that first afternoon like we had agreed she’d do. I made phone calls to all of the women’s dorms all over campus; no one had heard of her. Her old roommate had moved off-campus and had no idea what had become of Crystal. The next day I got a letter in the mail from her, stating that over the summer she had found a boyfriend back home, and was quitting school to work at Dairy Queen so she could be with him. I was crushed.

I don’t know if my breakup with Crystal was the catalyst, or if it just happened naturally, but over the next two years I developed a pretty severe lack of motivation. Looking back on it, I’m pretty sure I would have been diagnosed with clinical depression and placed on anti-depressants, had I known what was going on. But we didn’t know as much about mental illness back then as we do now, and in my mind I didn’t chalk up my lack of motivation to a medical problem. Depression puts people in a place where they are unable to derive pleasure from anything, and I was definitely in that place. I wanted nothing more than to sit around and watch TV. I lost all interest in going to discussion groups or playing games with my friends. I stopped going to parties. I went to class less and less frequently. I did less and less studying. By the spring of my third year, I had simply stopped going to class altogether, maybe dropping in once per week on some of them just to see what was still going on. Needless to say, when I got my grade notice with all D’s and F’s on it, my academic advisor wanted a word.

We both decided that a year off was what I needed. He mentioned the words “academic probation.” My mother had a hissy fit, but since she wasn’t paying the bill there was only so much she could say about it. We headed home, and I resigned myself to living at home for a year and actually working for a living.

That year at home cured me of whatever it was that was wrong with me. It also cured me of my bad attitude. I cut my hair. I started being nicer to people. I held down a job computerizing old birth certificates for the county. When the next August came around and it was time to go back to college, I was ready once again. This time, I found myself quite motivated to go to class, since the alternatives at the time were to join the military (wasn’t going to happen) or move back home permanently (which was even less likely).

I majored in Health Services Administration, which was basically something I picked at random. Even though I was now 22, I still had absolutely no idea of what I wanted to do with my life. I knew there was money to be made in the health-care field. I also knew that I didn’t have the motivation or the discipline to be a doctor, so Health Services Administration (HSA) was just something I just kind-of ended up with. My grades weren’t great, but they were good enough, and I graduated.

On graduating, I got an apartment in the town where I went to college. It was a nice town, and I had grown used to it (if not fond of it). There was also the matter that I had been steadily dating a girl named Caitlin for over a year, and I wasn’t going to leave her. Unlike my relationship with Crystal, this one was real. Caitlin was two years my junior and so had two years of college left when I graduated.

Caitlin was a very sweet girl from the other end of the state. We met at a party when she was a freshman. Like most of the freshman girls who were there, she was at the party to meet guys, and she was pretty bombed when she staggered over to me. I was more or less sober, having curtailed my drinking pretty drastically in order to be able to concentrate on my class load (which, by my junior year, was quite a bit more demanding). There was something in me that she found appealing – maybe it was my calm demeanor that contrasted sharply with the loud posturing of my testosterone-addled peers. We found that we had a lot of common interests, including horror movies, baseball, and travel. We took it slowly in the beginning of our relationship – since she was a freshman, I didn’t want to deny her the experience of dating other people. But for whatever reason we took to each other, and we were exclusive by the spring semester of her freshman year.

There were some differences between us, too. For one thing, Caitlin’s family was pretty well-off. Her dad was a dentist, and they lived in a very nice subdivision. It didn’t seem to matter to her parents that my family was from the other side of the tracks – they took to me like a fish to water. Her dad, especially, was always very kind to me and genuinely seemed pleased that I was dating his daughter. The fact that they were Catholic and I was more or less Protestant (I rarely went to church, as a child or as an adult) didn’t seem to bother them. Caitlin had as little interest in religion as I did, though we both professed to be Christians.

By Christmas of my senior year, Caitlin and I knew that we were going to be together - although neither of us had used the word “marriage” - after college, so I found a basement apartment and made it my home. Officially Caitlin lived in the dorms, but she spent most nights at my place. I worked while she studied, slept, or went to class, and we made plans for what would happen after she graduated.

A degree in HSA would have started me on a career path to be an administrator in a hospital or nursing home, or perhaps an executive in the burgeoning (at the time) field of managed care. However, there were no managed-care companies in the city were I went to college. The nursing homes weren’t hiring administrative personnel, and the hospital in town wasn’t hiring administrators (those jobs were reserved for people with connections to the management company’s shareholders). The hospital was hiring lab technicians on the midnight shift, and my degree with the word “health” in it impressed the lab manager, although the job didn’t require a degree, and he hired me. By the time Caitlin graduated, a job had opened up on the 3-11 shift, which wasn’t ideal, but I was glad to be off midnights.

Like a lot of the women who went to the university Caitlin and I went to, Caitlin had majored in Elementary Education, wanting to be an elementary school teacher. Also like a lot of the women at our university, Caitlin applied at the local school district, which had all the teachers it needed and had a waiting list a mile long, mostly filled with the names of recent graduates, Caitlin’s among them. She managed to find a job at a day-care center.

With two incomes, we could afford a better apartment, and we officially moved in together about a month after she graduated. If her parents cared that we were living together and not married, they didn’t let it show. Her mom came to help decorate, donating a lot of her old kitchen utensils and household goods. My stepfather came by and helped us with some minor repairs.

Once again, I was at a situation in my life that I had sort-of fallen into rather than planned to be in. There we were, two college degrees between us and two jobs that required only a high school education, in an apartment in the town where we went to college. In my childhood I had always planned to go to Florida the first chance I got. I’d had two chances, and still wasn’t there, but I was in a place where I was comfortable if not especially happy, so I made do.

I hated my job, and Caitlin just seemed to tolerate hers. I hated scraping snow off my windshield and slipping and sliding on the icy streets, but moving to Florida wasn’t an option – there was no money. There was no money for anything, really. Between student loans and our low salaries, we couldn’t even put money away for a wedding. Whenever we did manage to get a few hundred dollars ahead, something would go wrong with one of our cars and we’d give all of our money to a repair shop. Fortunately, Caitlin was on the pill, so at least we didn’t have the fear of bringing a child into this mix.

By this time, I had worked my way up to assistant manager of the lab. This meant a slight pay increase – something on the order of 45 cents more per hour, and it meant day shift hours, at least on paper. In practice, I was the fall guy whenever anyone on the night shift called in sick, so at least two nights per week I was in the lab.

My job at the lab was a stressful one. On the night shift, we’d get a steady supply of samples, mostly from the emergency room but also from other departments in the hospital. Each lab order would be of the utmost importance – the surgery department would want their results stat, as did the emergency room, the pediatrics floor, etc. On the day shift, there wasn’t as much urgency, but there was a much greater workload. As assistant manger, my boss, the manager, would take most of the heat whenever a doctor would try, not so patiently, to explain why his lab orders are not to be done last. My boss would be all “Yes, sir… understand sir… never happen again sir…,” and then make a big deal of reprimanding me (as if I had anything to do with it) in front of the doctor. Then, once the doctor was out of earshot, he’d be my best friend again. It was to laugh.

I was routinely buying lottery tickets at this time. I didn’t spend any more than what I deemed reasonable – five bucks here and there. It wasn’t an amount of money that really hurt us, and Caitlin, even though she had no interest in the lottery, didn’t complain. The money I spent on lottery tickets, like it always had done, let me spend a few hours daydreaming about what I’d do with the money. Caitlin and I were more or less happy, though we were broke, stressed out, and in jobs that we didn’t like. We had each other, but we both wanted more, and had no real means of getting it or plans to make it so we could get it. My lottery purchases afforded a fantasy; a daydream. That daydreaming came to an abrupt end the night my numbers came up.

CHAPTER TWO: THE BIG WIN

I was a few months shy of my thirty-second birthday in the spring of 2002. On a Friday afternoon after work, I stopped at a gas station and filled up my gas tank. As I did nearly every Friday night, I bought $5 worth of quick-pick tickets for my state’s multi-state lottery. I paid no attention to the numbers as I put the ticket in my wallet. I got into my car and drove home.

That Friday was no different from any other Friday. I got home at about 3:30 (I worked 7-3 at the lab) and got on the internet, checking my message boards and playing games in the two hours or so I had before Caitlin would be home. I cooked dinner – I have no clue what I made. Doubtless it was something quick, cheap and easy, like Hamburger Helper. Caitlin got home, we talked about this & that, ate dinner, and sat on the couch and watched a movie on TV. I figure that it was some time as the movie was winding down that, several states away, some ping-pong balls were falling down a chute in a way that was going to change both of our lives forever.

On Saturday morning, I got up like I usually did on Saturdays. All week I would drag myself out of bed in time to be at work at 7:00, dreaming of Saturday when I could sleep late. Come Saturday, I would be wide awake by 7:00, and this Saturday was no different. I got on the internet and checked my e-mail. Then I checked my message boards. Then I logged on to a game site, before I realized I needed to check my lottery numbers.

At first I thought it was a mistake. I was so used to seeing only one or two of my numbers, usually none, appear on the screen, that I thought maybe I was looking at last week’s numbers. Or maybe my eyes were deceiving me. I checked again. The numbers on the top line of my ticket, all six of them, matched the numbers on the screen. The dates matched as well. I checked again. And again. And a third time.

I could feel my blood pressure dropping as I realized what was happening. To be honest, it wasn’t a pleasant feeling. If I had to describe it, it almost felt like what one would feel when feeling dread – kind of like when the nurse points the needle containing the flu shot at your arm. That instant rush of dread that washes over you as realize something unpleasant is about to happen. I tried to call Caitlin, but my voice was suddenly hoarse.

I walked into our bedroom on wobbly knees and tapped Caitlin to wake her up. “I need you to come look at this,” was all I said. Not, “Hey Caitlin, we won the lottery!” or anything dramatic like that. Just a gentle request for her to come to the living room and look at something on the internet, like I had done several times before in our relationship.

She sat down at the computer and wondered for a few seconds what she was supposed to be looking for. I handed her the ticket and pointed at the numbers. Her jaw dropped. She looked at me, then looked at the screen again. Then she asked, “What does this mean?” We both looked at the ticket again. Not surprisingly, it still looked exactly like it did when I bought it: a pink and white scrap of paper with black ink – I’m not sure if I expected it to glow, or what. “It means we won the lottery,” I said.

The advertised jackpot in the multi-state lottery in which I had bought the ticket was $77 million. I would learn, when I turned the ticket in that following Monday, that there was one other winner in another state. That meant my share was $38.5 million.

In any lottery jackpot, here is how to figure out how much money you’ll get, after taxes, if you take the lump sum. Take the advertised jackpot, divide by three, and add ten percent. So, for example, if the advertised jackpot is $60 million, and you took the lump sum, after taxes you would get about $22 million. 60/3 = 20, and 20 + 10% = 22. This is only meant to give you a general idea and is not exact; plus, things like income taxes in your state will vary greatly, so that, too, will affect the bottom line. But this formula is generally pretty close.

So anyway, I held in my hand a pink and white scrap of paper, for which I had paid $5, and whose value in terms of ink and paper was a fraction of a cent, which was worth $38.5 million. Since I would take the cash value option, after taxes, I would wind up getting $14.1 million and quite a bit of change, consistent with the formula that I explained in the previous paragraph.

I’ve often been asked to describe what it feels like to win the lottery. After that initial feeling of dread, which only lasted a second or two, had passed, the feeling that washed over me was one that defies description. I can best describe it as what it would feel like for a Chicago Cubs fan watching the Cubs win the World Series, a cancer patient learning there’s a cure for cancer, and a detective finally arresting a serial killer, all rolled into one, and then some. It was a rush that drug addicts crave – and I would spend a good part of the next few years chasing that high. The feeling lasted for all of three days. Once I turned in the ticket, things changed. But more on that later.

As Caitlin and I stood there in our apartment, holding a priceless piece of paper, suddenly the idea of leaving our home seemed like a very bad idea. Not knowing what to do next, we put the ticket in the safest place we could think of – deep inside a copy of the Bible we had. Just to make sure I didn’t forget where I put it, I marked it down - the first page of the book of Amos.

We sat down in our kitchen and mapped out a game plan. We couldn’t do anything with the ticket until Monday, when we would take it to our state’s lottery office and turn it in. We figured it would be about two weeks before we got an actual check (we were right). Obviously, we’d be moving out of our apartment. Caitlin knew I’d always wanted to live in Florida, and we’d talked a time or two about it, but there was never enough money. Now there was.

Home prices vary greatly across the United States, and even within regions of the U.S. there’s quite a bit of variance between prices in the city vs. in the suburbs vs. in a rural area. Most people live where they do because that’s where their jobs and/or their families are. Rare is the person who has the money to just pack up and move to another city simply because they want to, and the absence of a job is of no consequence. Caitlin and I were now such people. It was a weird, but empowering, feeling.

I went to a nearby bookstore and bought a copy of Unique Homes, a luxury real-estate magazine. Ironically, I didn’t have enough cash in my pocket to pay for it, and wound up writing a check. Even more ironically, the next payday (Caitlin’s) wasn’t until next Wednesday, and we had so little money in our bank account that the next check I wrote probably would have bounced – not that it would have made a difference, but still.

Looking through the magazine, I got a feel for what we were in store for, and also for what people will pay millions of dollars for the privilege of doing. There were homes in that magazine for which my $14.1 million would have paid about a half, or less, of the price. Nevertheless, I found the Florida real estate market to my liking. There were several homes in our price range (not that we had any idea of what our price range was), and I was confident that we’d find something we liked.

We then realized that we now had enough money to get married. We had lived together for five years and had talked about tying the knot, but we never had enough money. There were times when we didn’t even have enough money to buy a marriage license. We agreed that, once we got the check, we’d be on a plane to Vegas the next day. I thanked Caitlin for not being the kind of girl who insisted on a church wedding that would take months to plan. She joked, saying “I’ve been waiting for five years. I’m not waiting any more.”

Caitlin called her parents. I can still hear her mom screaming “What?!?” through the phone, and then laughing. I’d always regarded Caitlin’s parents as rich – after all, her dad was a dentist. I’d first been to their house during our courtship in college, and I was duly impressed. A 2,200 square-foot McMansion, complete with a three-car garage, a fireplace, a pool in the back, and a speedboat in the driveway - basically, it had all the things that my home as a kid lacked. And, the neighborhood was nice and didn’t have vandals and wannabe drug dealers or other punks vandalizing or breaking into cars. I remember Caitlin once confiding in me that her family had money troubles just like any other family. They lived paycheck to paycheck, just like the rest of us. They just got more mileage out of their paychecks.

Caitlin’s conversation with her folks lasted about an hour. I remembered her saying things like “wedding” and “Las Vegas” and “buying a house in Florida” and “we’ll pay to fly you down anytime you want to come.” She was all smiles when she hung up.

I called my parents. My mother gasped in shock when she heard the news. Then, her voice filled with a mix of awe and dread, asked “What are you going to do now?” I told her about our plans; to get married in Vegas, maybe take a cruise for our honeymoon, and about how I was finally going to get out of the Midwest and head for Florida. Mom re-iterated several times during our conversation that she was happy for us. She put my stepdad on the phone, and I could almost hear his ear-to-ear grin on the phone. We hung up after about an hour.

There’s nothing much to say about what happened over the following two days. We checked the numbers on the computer at least a hundred more times. We leafed through our luxury real-estate magazine until it was ragged. Caitlin looked over our closet, dreaming of the nice clothes with which she would fill her next closet, wherever that would be. All we could do was wait.

I had daydreamed several times throughout my career about quitting my job. I was going to proudly tell my boss, “I quit!”, and on the realization that he was going to lose his best employee, he would quiver and sob, proclaim repentance for his misdeeds, apologize for being such a jerk, and offer me a substantial raise. “No!” I would say. “I don’t need you or your piddling little salary! Nyaa! Nyaa!,” I would say, over his sobs. He would continue to plead, and I would continue to refuse his pleas. Everyone in the hospital would hear the noise, and would see me proudly standing over my sniveling boss and telling him that I was so far above his petty demands on me as to laugh.

What actually happened was pretty anti-climactic. I just didn’t go to work the next Monday – that was all. The phone rang at about 7:30. My boss asked if I was coming to work. I said, “No.”

Silence. “Are you coming to work tomorrow?”

“No.”

More silence. “Oohhh, kay. Are you coming to work ever again?”

“No,” I said flatly.

“Alright then, see ya.” Click.

That was it.

Caitlin took the high road. She called her boss and told her that she wouldn’t be there today (this was the Monday after the drawing), and that she’d be there on Tuesday, and she was submitting her two-week notice effective today. “What’s wrong?” her boss had asked. Caitlin had promised to explain when she got to work on Tuesday.

We went to our state office building that housed the lottery commission. I told the nice lady at the lottery window that I had the winning jackpot ticket. She beamed, and then asked to see it. Nervously, I pulled the ticket out of its hiding place between Joel and Amos. It was still pink and white, and it still looked like every other lottery ticket I had ever bought. She looked at it and then looked at her computer screen with the winning numbers, and smiled again. Then she ran the bar code under a scanner. The machine hesitated, then beeped. She smiled a third time. “I’m going to need you to fill out some papers,” she said, and then got on the phone.

Before I knew it, Caitlin and I were standing on a stage while dozens of cameras flashed around us. The lottery director, dressed in his suit, placed his arm around me and smiled his best smile, and handed me a big piece of cardboard that looked like a check, complete with my name on it. Reporters asked questions, and the words seemed to come out of my mouth in slow motion. “Lab technician. Caitlin. Met in college. 31. Pay off bills. Las Vegas. Florida. Pre-school teacher.” Then after a few minutes the questions stopped, the cameras stopped flashing, and the press went on to something else.

We were back in the director’s office. He handed me a pamphlet about how to handle a cash windfall (to this day I have no idea what happened to that pamphlet). He spoke very gravely about being careful how we spent the money. He mentioned lawyers, accountants, financial planners… it all seems just a jumble in my head. Then he smiled his best smile, congratulated us again, told us we’d have a check in about two weeks, and told us his secretary would show us to the door. His head was back in his paperwork before my hand hit the doorknob on his office door.

At 6:00 that evening, all hell broke loose. My name had made the local news, and almost immediately the phone started ringing. The first caller had a son with asthma, but she didn’t have enough money to buy his life-saving medicine. Surely someone like me could come to her house and give her a couple hundred dollars to save the boy’s life. The next caller had just lost their home to a fire. The third and fourth callers had fantastic investment opportunities that were perfect for me. I took the phone off the hook after the seventh or eighth caller.

Then people started knocking on our door. First were neighbors, offering hearty congratulations, and none-too-subtly hinting that a few thousand bucks would be nice. We laughed and smiled, but a few seemed to actually think I was going to cut a check right there on the spot. We decided to leave the apartment after a guy we had never seen before walked in with his hand out and said that we should give him a hundred bucks, since we had so much money. When I told him that wasn’t going to happen, he shot me a look that told me he meant business. After Caitlin grabbed the phone and made it obvious she was dialing 911, he turned around and left, muttering obscenities under his breath. We headed for a hotel room.

Imagine being a multi-millionaire who can’t get a nice hotel room because your credit card is maxed out. That’s what happened to me and Caitlin that first night. By all rights we should have been able to stay at a nice hotel in town, but wound up going to a Comfort Inn because we only had enough available credit on our credit card to stay there. The desk clerk at the hotel apparently hadn’t seen the news, because she didn’t look twice when she copied my name from our credit card. I told her in no uncertain terms that we were not to take any phone calls. She indicated that she understood, and we holed up in our hotel room.

On Tuesday, Caitlin went to work, and I went to our bank. The tellers must have recognized me from the news, as they all made a big fuss of me, asking me what I was going to do with all that money, etc. We made small talk for a while before the bank’s branch manager came to see me. We went to his private office, and spoke of account insurance, possible investment plans such as CD’s, and things like that. I didn’t have the heart to tell him that I’d probably be withdrawing every cent a few weeks after my millions were deposited, and transferring my accounts to a bank in Florida. Besides, what I was really there to talk about was my credit card situation. Surely, I explained, a man who was due to come into several million dollars in a few days could have a higher credit limit than $5,000 on his credit card.

Unfortunately, there was nothing the bank manager could do. Our bank didn’t issue credit cards. He suggested calling my credit card’s customer service number, but I didn’t think they were going to buy my story that I had won the lottery. I mentioned a loan, but he said that wasn’t possible because of my credit score (!). Finally I flat-out told him that if his bank wanted my continued business, which would undoubtedly be very profitable for the bank, he would find a way to keep a soon-to-be multimillionaire from being homeless. After some hemming and hawing, he agreed to credit my account a few thousand dollars. I signed a promissory note, and then asked to use the phone.

I paid off my credit card on the spot – something that I had never thought I would be able to do. I didn’t even get the satisfaction of talking to a live person – it was all automated. Then I called my parents and Caitlin’s parents and told them what was going on, and that we would be incommunicado until we got cell phones, which I hoped to accomplish that day, and to hold tight. Then I withdrew a few hundred bucks in cash so Caitlin and I would be able to buy food over the next couple of weeks. Then I bid my bank a very disappointed adieu.

I went to, we’ll call it “ABC Wireless,” to sign up for cell phone accounts for myself and Caitlin. They ran my credit report and turned me down – something about late credit card payments. To say I was stunned would be an understatement. I thought of yelling, “Do you know who I am?” but decided I’m not that kind of person. I went to “DEF Wireless” and had essentially the same experience. But fortunately they had a sort-of backup plan where you can tie your phone account to a credit card, and since I now had quite a bit of available credit, I was in business.

Back at the hotel, word must have gotten out about who I was, since I noticed the hotel workers whispering and pointing as I walked past. Caitlin was in the room, too, even though she was supposed to be at work. Somehow the name of her workplace had made it through the grapevine, and strangers were showing up at the front door (not a good thing at a daycare center!) asking to speak to her. To make matters worse, many of the employees were hitting her up for money. Everyone, it seemed, had a pressing financial problem that Caitlin, as a dear friend, was in a perfect position to solve. Caitlin and her boss decided that it would be best for the work environment if she left. She was only too happy to do so.

Oddly enough, we needed Caitlin’s paycheck that was due to come the next day. Our rent was due, and even though we weren’t living in our apartment, and indeed would never spend another night there again, we didn’t want to be deadbeats, or run the risk of the landlord throwing our belongings onto the street. We also had other bills due, and since at the time we were only rich on paper, and I had blown my entire loan from the bank on paying off our credit cards, we would have to pay them with Caitlin’s paycheck.

The following Wednesday, a week and two days after I had turned in my winning lottery ticket, the check arrived. In the mail. I was fortunate enough to go and get it from our apartment complex’s mailboxes at a time when there weren’t any other people there, which was a good thing. My check had the state Comptroller’s Office’s return address on it. It was blue and white. It basically looked like all of my tax-return checks, only it had more digits on it. Just like the lottery ticket, it didn’t glow or anything like that. It was just ink and paper, like the ticket.

The business of avoiding other people had gone on for over a week, and it was wearing on us. We ate only drive-through meals, since we learned quickly that eating in a restaurant brought unwanted attention. We couldn’t so much as go to a movie without complete strangers asking me for money, which I found unbelievably ballsy but no less intrusive. We had basically been prisoners in a hotel room, watching daytime TV and eating fast food. We were ready for a change.

We went to the bank and deposited the check. The tellers all gathered around to gawk at it, and then the branch manager emerged from his office to make his presence known to me. I asked him if he’d mind calling Visa, explaining who he was, telling them that a valued customer of his would be applying for a high-limit credit card, and was there anything that could be done? He got on the phone, said a few hushed words, got transferred a few times, then handed me the phone. I don’t know who, exactly, it was at Visa that I was speaking to, but they were all too eager to issue me a new credit card, with a one-million-dollar credit limit. It would arrive via overnight mail the next day.

I went to the Dodge dealer to buy a Viper – the same dealer that had sold me my Neon, at a very high interest rate due to my credit score, two years earlier. I told the salesman I was there to buy a Viper. He hesitated a second, then asked if I would be making a trade. I pointed to the Neon. The salesman looked at the Neon, looked at me, and then said, “I think you might find more vehicles to your liking at our pre-owned lot next door.” It took me a few seconds to realize that I was being given the bum’s rush, and once I understood what was going on, I simply turned and walked out. I was too mad and too embarrassed to try to continue the conversation.

Back to the bank, this time to get a certified check. Then I drove about 75 miles to a nearby city, to another Dodge dealer. The first person I saw, I showed them the check. I made it clear that I was in town to buy a Viper, and I was trading in my Neon. This time, the salesman didn’t give me any grief at all (a certified check will do that). I test-drove a few, found one I liked, wrote the check for sixty-three thousand dollars and some change, and headed home in my new ride. I would later learn that the two dealerships were owned by the same investment group, so in an indirect way the first dealership got my money anyway. Oh well. At least it wasn’t the same salesman.

Buying Caitlin’s Lexus was easier. When you pull up in a Viper, the salesman doesn’t question whether or not you can afford to buy a Lexus. Another certified check helped expedite matters.

We spent the rest of the day at our hotel, our new Viper and Lexus in the parking lot of a Comfort Inn, putting our new checking account and credit card to use. I called a well-known moving company and told them to go to my apartment, pack everything up, and put it into storage until further notice. I called our landlord and told him we were terminating our lease, and that a moving company would be by in a couple of days, and to let them in. He got angry and said that he’d be keeping our security deposit since we broke the lease early. Like I cared. I cancelled our utilities and paid the final bills. I called a travel agent and pre-paid for our honeymoon cruise to Hawaii. We paid off every outstanding bill we could think of. I paid off my student loans, which was surprisingly unsatisfying. What I had hoped would be a big deal turned out to be nothing more than mailing a check to a special address, and the representative on the other end of the line didn’t seem the least bit impressed, maintaining an attitude that was polite but otherwise all business. Apparently the student loan financing company took a while to warm up to the idea that my bill was paid in full; for the next three months, I got a bill each month for $0.00. Finally the bills stopped. I guess someone in their Accounts Receivable department put two and two together.

Finally, when every imaginable loose end was tied up, and every account that had either my name or Caitlin’s on it showed a zero balance, I made arrangements for our wedding. We headed for the airport the next morning. Two weeks later we would be back in town long enough to pick up our cars and head for Florida, and then neither of us would ever set foot in that town again. Or so I hoped.

CHATPER 3: LIFE AS A MULTI-MILLIONAIRE

Money talks. And with the possible exception of Washington, in no city in the United States does money talk as loudly as it does in Las Vegas. Do you need eight front-row tickets to Cirque du Soleil? Try asking the concierge to swing that for you on a few hours’ notice, and see what response you get. Then go to the tables and, between you and your friends, put down four hundred thousand dollars in action. The pit boss notices. Some phone calls are made. And then those Cirque du Soleil tickets somehow make their way into your hands.

For another example, consider room accommodations in Vegas. For the most part, casinos’ websites will list the price of regular rooms and a few suites. These suites that are advertised to the general public are generally the most basic suites that the casino has to offer. The casinos will have better suites, often outfitted with grand pianos, private concierges, and the like. But they aren’t offered directly to the general public, and for good reason: the general public isn’t likely to see the inside of one of those suites except when watching a Travel Channel documentary. For the most part, these suites are comped to high-rollers. That explains why, when I tried to make my reservation, I had such a hard time convincing the agent that I wanted a bigger suite: she must have figured that I was a high roller looking to redeem some clout (in Vegas’ early days, a high-roller’s clout was a nebulous thing that depended upon the player’s relationship with the house; clout can now be quantifiably measured in the form of casinos’ rewards club points). Since I had neither clout nor rewards club points, the agent wasn’t clear on how I thought I had access to a bigger suite than what was on the website. But what I did have was a Visa card with seven figures of available credit, so I got my suites. Money talks.

Caitlin and I; my soon-to-be father-in-law Roger; Caitlin’s mom, Betty; my mother and stepfather; and my father and his wife (he was now on his third), stepped off the plane at McCarren International Airport in Las Vegas. My mom and stepdad had been there a time or two in their lives. My father had been through there once. None of the rest of us had ever set foot in Vegas. We headed for the ground transportation desks and arranged for a Hummer stretch limo to take us to our hotel, the Bellagio.

We guys headed down to the casino after we got settled into our suites. The “girls,” as we took to calling them, were going on a shopping spree throughout the Bellagio’s high-end shopping district. It was about 2:00 P.M. We agreed to meet back at 6:00, decide on our evening’s entertainment, and get some food.

The four guys headed for the blackjack tables. I found one with table limits of $25-$5,000 – perfect. We walked up and sat down. I handed the dealer my credit card and asked him to debit four hundred thousand dollars. “Yes, sir.” He didn’t seem fazed or impressed in the least. He simply took my card, scanned it, punched some numbers, and waited. The machine must have approved, because the dealer’s next words were, “How would you like that, sir?” This wasn’t a question I was expecting, and without really knowing what I was doing, said “thousand-dollar chips?” The news that he was going to have to count to 100 four times didn’t seem to bother the dealer in the slightest. He merely said, “Very well, sir,” grabbed some chips from a nearby cabinet, and started counting.

By now we had the pit boss’ attention, and out of the corner of my eye I saw him make a hushed phone call. A few minutes later a casino host came and introduced himself to me. I found this weird, since I was the youngest guy at the table by twenty years, but I guess the pit boss had told him that I handed over the credit card, so he figured I was the one paying the bills. He asked me how we liked our rooms, had we made plans for supper, was there anything he could do to make our stay at the Bellagio more comfortable, and so on. To be honest, I actually found him to be kind of a pest, but the alternative was watching the dealer count, so I humored him. I must say that he seemed genuinely distressed that we didn’t have plans for dinner. He seemed to wrap up his questions just as the dealer was finishing with his counting, and politely excused himself. Out of the corner of my eye I saw him get on the phone.

Prior to this experience, I had been in a casino exactly twice in my entire life. The first time, I was around nineteen or twenty, and my grandmother and I went on a chartered bus trip to an Indian casino in a neighboring state. Grandma played bingo while I hit the slots. The second time was shortly after college; I had gone to Topeka to visit an old classmate and on the way home stopped at a newly-opened riverboat casino in Kansas City, again hitting the slots. Both times I promptly lost my shirt. Apart from the lottery and my two casino trips, my only gambling had been the odd night at bingo and the horse races once a year or so (and a couple of trips to the dog races when I went to Daytona Beach for Spring Break). I had never once played a table game in a real casino.

The dealer separated our money into four stacks and passed one out to each man at the table – one hundred thousand dollars, in thousand-dollar chips, each. Each of my guests by all rights could have pocketed those chips, gone to the window, and left that casino with a hundred large. No one did, apparently figuring that they were playing on my dime.

The dealer went to work, passing out the cards in a quick, fluid motion that would put a ballet dancer to shame. None of us men at the table knew much about blackjack – we knew how the game was played, of course, and understood basic strategy in the most rudimentary sense. On the first hand, I had a ten up and a four down. The dealer showed an ace. He offered insurance. We all knew that insurance was a sucker bet, so we passed. My father, to my right, was showing a king. He hit. A six came out. He stood. My turn: I hit. A ten – busted. Next was my stepdad – he showed a two. He hit, got a seven, and stood. Roger showed a ten up. He stood. The dealer turned over his down card – a king. He had 21. All four of us lost. Four thousand dollars to the casino, in about 45 seconds.

We played steadily for the next few hours. A waitress turned up asking for our drink orders, and the host came by to tell us that our table was entitled to top shelf products, on the house. Roger had scotch on the rocks; my stepdad had Bud Light; my dad had Skyy Vodka and cranberry juice; and I had a 7 & 7. So much for top shelf. My dad asked for a cigar, and someone showed up with about eight boxes on a cart. Dad seemed to know what he wanted, since he went right for one of the cigars without even looking at the other ones. He lit it up, and it smelled for all the world like he was smoking a turd.

None of us played particularly well or particularly badly. By the time the girls returned, each of them carrying several shopping bags and grinning from ear to ear, my dad was up twenty thousand; I was down twenty-four thousand; my stepdad was down twenty six thousand, and Roger was up two thousand. Suddenly I realized that I had three hundred and seventy two thousand dollars worth of chips on the table. I could have cashed them in, but walking around with that kind of cash didn’t make any sense. The casino could have cut me a check, but that didn’t seem right, either. Realizing my dilemma, the dealer asked “Shall I credit your credit card, sir?” “Oh, yeah, good idea,” I said. He dutifully counted the chips again, swiped the card, and that was that. If either Roger or my stepdad realized that the money that they had won had just gone back into my credit card account, they didn’t seem to notice. Maybe to them it was play money, since it was my account they were playing on. No bother – I would wind up paying off the mortgages for both men a little while after we left Vegas, so the pocket change (which was mine anyway) that went back into my account was not important.

We had tickets to an 8:30 show – eight tickets to front-row seats at Cirque du Soleil had somehow found their way to my hands – and it was getting time for dinner. The pit boss recommended a fine Italian restaurant, at the Bellagio, of course, and made 6:05 reservations for us. And of course, our meal would be on the house. Roger knew a thing or two about wine, and took full advantage of our comped dinner, drinks included, by ordering a bottle of 1961 Chateau Margeaux, a bottle of wine that I learned was worth about $1,500. It tasted like rotting grape juice, but everyone pretended to love it. The food was exquisite; and Cirque du Soleil more than made up for the nasty wine.

The next day, Caitlin and I got married. We had been living together officially for five years, always talking about getting married but never being able to do it. Little girls dream of having big weddings, complete with candles, white horses, the whole bit, but Caitlin didn’t get that and didn’t seem to want it anyway. The chapel we picked was tasteful, even by non-Las Vegas standards, and the only witnesses were the six parents we brought with us. Caitlin was an only child and so had no siblings to invite. My siblings couldn’t get time off work and arrange childcare for their kids on such short notice. Neither of us really had any friends – Caitlin hadn’t kept in contact with her college friends and had fallen out with her workplace friends, and I just didn’t have any friends at all. So our wedding was small. One of the most cherished and beautiful memories I have of Caitlin was her that day – a simple white dress, flowers in her hair, and a pair of white shoes that I would later find out she paid $1,500 for (and which she never wore again). For all of its limitations, it was probably the happiest day of our lives.

We spent the rest of the day walking up and down the Las Vegas strip and checking out the sights. I had a jones to go back to the tables, but didn’t tell Caitlin. We had lunch and supper at other casinos – this time paying for them – and wrapped up the night at another big-name Vegas show. I honestly don’t remember what it was. The next morning, we said goodbye to the ‘rents as they got on their planes home, and we got on our plane to San Diego, where we would catch our cruise ship to Hawaii.

The Bellagio had comped me four suites, $1,599 each, for two nights, for a total of $12,792, plus sales tax. They comped a meal for eight at about $200 per head, plus a $1500 bottle of wine, for $3100. They also provided me with eight show tickets, with a face value of about $150 each, for another $1,200. All in all, I figure the Bellagio comped me $17,092 in freebies before tax. I lost $28,000 at their tables. The house always wins.

At San Diego we caught ground transportation to our cruise ship. U.S. maritime law prohibits cruise ships from traveling between two contiguous U.S. ports (or at least, that’s how I understood what the travel agent had told me), and since San Diego and Honolulu are contiguous, we had to catch a charter bus from San Diego to some nearby town in Mexico and get on the ship there. Even though I would be staying in one of the ship’s largest and most luxurious staterooms, the transportation to Mexico can most charitably described as “egalitarian.” In other words, we were all put on a charter bus that was a step above a Greyhound.

Neither of us had ever been on a cruise, and in retrospect, it might have been better for us to start small on our first cruse. As it was, we got our passes and headed straight for our suite which, like our suite in the Bellagio, was generously-appointed and quite luxurious. We had our own private balcony looking out over the ocean, with a couple of deck chairs on it. We would spend most of our time, when we weren’t eating, sitting on our deck chairs and sipping frozen cocktails, and as such we missed out on a lot of the events that the cruise had to offer us. Nevertheless, the ship was stunningly beautiful, and the meals were exquisite, so there were no complaints. We were definitely starting to enjoy being rich.

Hawaii itself is quite a place. Before I actually set foot there, the impression I had in my mind of the place was mostly gleaned from Elvis movies, Travel Channel documentaries, and a very special episode of The Brady Bunch. What I found was a mix of the three, and quite a few things that I hadn’t expected. It was stunningly beautiful, to be sure, but also extremely crowded. And once you get away from the beaches, Hawaii, at least to me, seemed rather poor and, in some places, pretty desolate.

If you’re into adventure sports, like biking, surfing, and doing the zip-line, Hawaii is just the place for you. If you’d rather just hang out on the beach, you can do that, too. The image I had in my mind of Hawaii included 30-foot waves crashing into the Bonzai Pipeline on the North Shore of Oahu. Unfortunately, that wasn’t to be so. Our shore excursions didn’t take us there, and the 30-foot waves only occur during a couple of weeks in the winter. We were there in the spring.

As cruise passengers, we didn’t have a hotel room, per se, and instead would return to our stateroom on our ship. We paid for several shore excursions, some of them not worth the money. Biking around a volcano sounds exciting, but when you’re out of shape, biking in the mountains is more of a chore than a diversion. And looking at desolate expanses of rock, when you’re in a tropical paradise, is a little unnerving. The snorkeling, however, was awesome, as was the fire-dancing show that we watched.

All in all, Hawaii was a mixed bag. I enjoyed the tropical beauty, but it contrasted pretty harshly with the crowded cities and the desolate landscapes and pineapple farms deeper into the islands. There was fun to be had, but I guess my expectations were higher. I made vague plans to come back again some day, but those plans never materialized.

We returned to our adopted home town from our honeymoon. From the time the plane landed until the time we left the city limits was less than an hour. All that we had in that town was our cars (a moving company would be moving our belongings, which at the time were in storage, on my call). We picked up our cars, me in my Viper and Caitlin in her Lexus, and headed to Florida; Miami to be specific.

With the whole of Florida to choose from, we picked Miami (this decision had been made over frozen margaritas as we sat on our deck chairs on the outbound voyage to Hawaii). We definitely wanted to live on the ocean, so Orlando and the rest of the interior of the state was out, though it probably would have been cool to drive over to Disneyworld any time we wanted. Since we wanted to live on the ocean, we had to decide between Florida’s two coasts. I had been to both coasts in my time (once to Tampa and multiple times to Daytona Beach). Caitlin had no preference, but I preferred the bigger waves of the Atlantic Ocean, so the Gulf Coast was out. Jacksonville was far enough north that I was concerned about being chilly in the winter. We had both been to Daytona Beach as college students, but Spring Break had moved to Cancún by this time, and Daytona’s aesthetic appeal was minimal. Besides, we wanted a larger city with some more action, so that left Miami.

The drive took us two days. We pulled into Chattanooga and found a hotel relatively early that first day, and I got on the internet in the hotel’s business center. I managed to score us a hotel room in South Beach and an appointment with a realtor. We got an early start the next day and rolled into Miami late that night. We were up bright and early the next day for our appointment with our realtor.

The first few houses the ren altor showed us were on the Intercoastal Waterway, which in my mind was a fancy word for “river.” The realtor explained that this was preferable to actually living on the beach, because you could dock a boat on the Intercoastal Waterway and then, if the mood struck you, take it out to the ocean. You couldn’t dock a boat if your house was on the beach. I explained to the realtor that we didn’t have a boat and didn’t plan on getting one, and we wanted to live on the actual beach, and not on a river that I could float down to get to the ocean, and in a house and not a condo. The realtor told us that for that to happen, if we wanted to stay within our budget we’d have to go quite a bit further north, a good half an hour outside of the heart of the city. Fine by me, I said, and the next few houses she showed us were more in line with what we wanted.

In the late spring of 2002, I paid $3.1 million for a house in a town that, until the day before, I had never set foot in. It was a 2,000 square-foot, Mediterranean style house (the realtor described it as a hacienda) with four bedrooms, a media center, a fireplace (in Miami!), three bathrooms, and a host of other amenities that went over my head. It was on the beach, and that’s what mattered to me. We were in a northern suburb of Miami, half an hour’s drive from the city.

The house was bare when we first looked at it, but the realtor said that, for an additional hundred thousand, it could be “designer furnished,” whatever that meant. I added another hundred thousand to the check I wrote. I asked the realtor why the first owner had left such a beautiful house. I had hoped she would say that its former occupant was some athlete who lived there in the off-season and whose name I recognized, but as it turned out, all she said was, “the previous owner didn’t get to spend as much time in it as he would have liked, so he decided to sell it.” What did he do that kept him from his beautiful beachfront mansion? He ran an unspecified (by the realtor) business… in Portland, Maine.

We spent a few more nights at our hotel while the movers brought our belongings and the “designer furnisher” went to work. We would wind up donating nearly all of our old belongings to Goodwill. The designer furnishings were much nicer, though I hasten to add that the designer never actually asked us what kind of design we wanted. Not that it mattered – whatever she did seemed to be just what we wanted. The main living room had a generic upscale feel to it; the master bedroom and the kitchen were both decorated in bold tropical colors. Our “designer furnishings” even included kitchen supplies, but we donated most of those to Goodwill when we replaced our entire set of kitchen goods with things we bought in Little Havana – but more on that in a moment.

We moved into our fully-furnished, and fully-paid-for, beachfront mansion on a Thursday afternoon. Needless to say, it was to our liking. The house was upscale without being opulent, and the furnishings were comfortable, and of course, brand-new. The media center was a small room with a big-screen TV and top-of-the-line audio equipment, which suited me just fine. The master bedroom seemed bigger than our old apartment. The house had a fireplace, in which I would build exactly two fires: once was that first night (never mind that the temperature outside was 85 degrees), because I had a fireplace (I’d never had one at any point in my life until then) and dammit, I was going to build a fire in it; the other was on Christmas Eve, simply because it seemed like the right thing to do on Christmas Eve (never mind that the temperature outside was 77 degrees). Outside, the pool was filled with crystal-clear water, and a little rock waterfall at one end added to the back yard’s ambiance.

The crème-de-la-crème, of course, was the home’s beach access. From the back yard I followed a little wooden sidewalk about 30 feet, over the grass, onto the beach. In front of me was the Atlantic Ocean, in all its vast emptiness. And as I looked out on the vast expanse of sea, being vaguely aware that Africa was on the other side, I wondered what was going on over there: were men my age looking across the ocean, wondering what was going on in Florida? I sat on the sand and let the warm waves wash over me. I had arrived.

One thing that caught us by surprise about our new home was how utterly dead the neighborhood was. I had hoped that my neighbors would send out the welcome wagon to me and Caitlin, and we’d have nightly neighborhood cookouts on the beach. I even hoped that I’d get to hobnob with some famous athletes whose names I recognized. The reality was that hardly anyone was ever there. Maybe once per week a BMW or Porsche would pull past the guard gate, and I’d see it come and go from the neighborhood over the course of a couple of days, then they’d be gone. At Halloween, Caitlin and I would spend close to $3,000 making our front lawn look like ghostly pirate ship had shipwrecked in our front yard; it was complete with fog, skeletons, tattered pirate flags, even a miniature rotting pirate ship. Not a single trick-or-treater came to our door. At Christmas, we would be the only house on the street with lights on it. We would eventually come to learn (by asking around) that most of the people who owned a home in our neighborhood rarely spent more than a few days per year in it.

One night, a few days after we moved in, we tried to order a pizza. I gave our address to the guy on the phone.

“I’m sorry, sir, that’s out of our delivery area.”

“But you’re the closest one to my house,” I said.

“I’m sorry, but it’s still out of our delivery area.”

“It can’t be more than two miles!” I countered.

“I’m sorry, but it’s out of our delivery area. We’d be glad to have you come pick your order up.”

“No thanks.” Click.

I hung up the phone, a multimillionaire in a beachfront mansion, who couldn’t order a goddam pizza. I would later learn from a man who used to work for an area pizza place why they didn’t come to my neighborhood. It seems that they used to, at one time. But they would get very few orders, maybe two or three per month. Whenever a driver would come to our neighborhood, the delivery would go like this:

The delivery driver would pull up to the guard station. The guard would say, “What are you doing here?” Not, “How are you this evening?” or, “What can I help you with tonight,” but, “What are you doing here?” – as if the pizza sign on top of the car wasn’t a tip-off. “I have a pizza for a Mr. Jones,” the driver would say. The guard would take a deep breath and then give an exasperated sigh. “I don’t believe we have a Mr. Jones on this street. Are you sure you’ve got the right address?” The driver would say, “Yes, Mr. Jones. Such-n-such address.” The guard would let out another exasperated sigh, then make a big deal of picking up a phone book, taking his sweet time to look for the number, never mind that he had a clipboard right there with the names, addresses, and phone numbers of all of the homeowners in the neighborhood. “Yes, Mr. Jones, this is the guard station. There’s a man here claiming to have a pizza delivery for you. Is this correct? Very well, then. I’ll let him through.” The guard would tell the driver something to the effect of “Well, it seems you’re telling the truth. Fourth house on the right,” then he’d slowly press the button to raise the gate, picking up his walkie-talkie immediately afterwards. Another car would practically follow the driver the whole time he was on the block, and when he tried to leave, the guard would inevitably be on the phone, and would not press the button to let the gate back up until he was done with his phone call, which often lasted several minutes. The whole business of going through the guard gates would add 15 minutes to the delivery times, and since that would make all subsequent deliveries late, and since the residents of our neighborhood never tipped and so the drivers didn’t like to go there, pizza places just stopped delivering there.

Another funny (funny in an ironic sense) incident would happen around the Fourth of July. Since they can’t be shipped through the mail, and since selling them is illegal in both Florida and Georgia, I drove up to Tennessee to buy fireworks (a 10-hour drive for fireworks!), and bought about a thousand dollars’ worth. I knew they were illegal to buy in Florida, but I figured the police would look the other way at people actually launching them, especially since it was the 4th. Back at home, I sat on the beach and started launching mine. I expected to get the attention of the neighbors, and we could finally have that neighborly bonding thing that I craved. Instead I got the attention of the county sheriff. He none-too-politely informed me of the county fireworks codes, beach pollution policies, and a handful of other crimes. I thought for a minute he was going to cuff me, but once I showed him my driver’s license and he realized that I was essentially in my own back yard, he let me off with a lecture. Eight hundred dollars worth of fireworks went back into the box and into a closet to be forgotten about.

Miami being our new home, Caitlin and I decided to explore it. We had spent a few nights at a hotel in South Beach, and though the hotel suited us just fine, South Beach itself was a bit of a letdown. On the beach were well-tanned, well-oiled hardbodies; mostly people who were there be seen. The art-deco buildings lining the streets were filled with excruciatingly rich (richer than us) glitterati, and with elderly tourists (and presumably some elderly locals), strolling the streets in their walkers and motorized wheelchairs, oblivious (or apathetic) to the fact that they didn’t belong there. It was a bizarre mix of people, and Caitlin and I definitely didn’t fit in.

Our second night after arriving in Miami, I went into one of the famed South Beach nightclubs for my first and last time. At South Beach nightclubs, the cover charges start at about ten dollars and go up to fifty or more dollars. However, the cover charge is a secondary concern. Your primary concern is whether or not you’re going to be let in at all. The entrance to the club is guarded by a bald, muscular black man wearing an Armani suit, and, cover charge or no cover charge, if you don’t have “the look,” you aren’t getting in. “The look” is completely up to the discretion of the bouncer, but as a general rule, if you are over the age of 27 and/or have a gram of fat on your body, you don’t have it. I had two Benjamins in my hand, and that caused the bouncer to overlook my appearance and open the door for me. I realized almost immediately that I was out of my league. Every last patron looked like they had just wrapped up a day of work in the fashion industry. I was the oldest person in the room by five years. The music was blaring, and how the bartender heard me order a 7 & 7 I’ll never know. Apparently he didn’t, because what he served me was a vodka tonic. I sipped on my drink, being steadfastly ignored by every last person in the room, then paid my $25 bar tab and left.

Little Havana, on the other hand, suited Caitlin and me to a T. Despite what anyone may tell you, Little Havana is a great place to spend some time, at least during the day. The Cubans have a rich culture, and are very proud to display it to anyone. A walk down a street in Little Havana is a mosaic of music, color, tastes and smells. Artists line the streets, selling all manner of crafts and works of art. Caitlin and I found a set of hand-blown glasses (for drinking from), replete with a variety of colors, and a beautiful set of hand-made and hand-painted dinner plates, which promptly replaced our “designer furnished” dinner plates that we had never seen until we first ate on them. We also found a painting that we bought on the spot, for $2,000. It was a beach scene, with the sun rising (or setting) over a beach filled with lush and colorful vegetation. A Spanish fortress filled the foreground (I presume that it stands to this day in the artist’s native Cuba). We got home and threw away the lithograph of an orchid that our “designer furnisher” had hung over our fireplace and put the painting in its place.

South Florida’s Cuban community is adamantly anti-Castro, and fully supportive of the U.S. embargo against Cuba. However, you wouldn’t know it by watching Little Havana’s older men. Every last one of them, to a man, was puffing on a cigar. Either they were smoking smuggled Cubans (and thus looking the other way at their moral scruples about supporting Castro), or Miami single-handedly is supporting Nicaragua’s cigar economy.

As much as I loved the food offerings in Little Havana, I found the rest of Miami’s food scene pretty appalling. I couldn’t get a pizza delivered to my house for love or money, as I mentioned a few paragraphs ago. There’s plenty of sushi, seafood, and Nouvelle Cuisine to be found, but if that’s not your thing, you’re stuck at Applebee’s. For another thing, you can’t get a good dish of ice cream in Miami, or anywhere else in Florida for that matter, apparently. I had been through St. Louis more than a few times in my life and had developed a fondness for Ted Drewe’s Frozen Custard (and if you’re ever in St. Louis, by all means stop by); in Miami, unless you plan on going to Dairy Queen, you’re pretty much screwed if you want ice cream. I’d also developed a fondness for White Castles, another Midwestern delicacy. Florida offered Krystal’s, which were a pale imitation. And the corn-on-the-cob was a disaster. Growing up in the Midwest, I’d gotten used to corn-on-the-cob that was sweet and firm; Miami corn-on-the-cob was salty, soggy and bland.

Back at the house, Caitlin and I were making judicious use of our checkbook. We sent off donations to just about every charity we could think of. Ten thousand dollars here to the ASPCA, twenty thousand dollars there to Habitat for Humanity. The amount of money on the check corresponded directly to how strongly we believed in the cause we were donating to. We sent checks to environmental charities, anti-poverty charities, legal aid societies, women’s charities, children’s charities, Christian and secular charities. At one point, I think we sent five thousand dollar checks to both National Right to Life AND to Planned Parenthood.

We hired a maid, through an agency. A nice Cuban lady, who didn’t speak a word of English, came by our house every day at 10:00 and spent two hours cleaning up after us, which was nice but also made us feel a little guilty, especially when she cleaned the toilets. We saw a gardener drive his truck into our neighborhood every day and disappear into our neighbors’ lawns. We figured we might as well do the same, so I called the gardening company and added our house to the list. About once a week or so, a little Cuban gardener would come to our house, pull off a few dead leaves from our palm trees, spray something here and there, and then leave. For this we were billed $100 every month.

We were also quite generous to our families – well, mostly to mine. We paid off Caitlin’s parents’ mortgage, which was nearing maturity so there wasn’t much left to pay, so we bought her dad a motorcycle; her Mom swore up and down that she didn’t want us to buy her anything, so we didn’t. Caitlin was an only child, so there were no siblings to help out. Instead, we sent ten thousand dollars to the private Catholic high school from which she’d graduated, with instructions to buy books for the library – our hope was that they would buy some books besides the Bible and books by Catholic authors (they probably didn’t, but we didn’t keep track). We paid off my parents’ mortgage, also nearing maturity, and bought my mom a new Cadillac and my stepdad a new Dodge Ram; we also bought new vehicles for my father and his wife. For my siblings, we paid off their mortgages and their car loans, and set aside generous college funds for all of their children.

My mom, mercifully, had kept my cell phone number a secret from the family, but she wasn’t so guarded about my address. She probably just wanted my cousins, and friends of the family, to be able to send me birthday cards and whatnot, but what they wound up sending were requests for cash. Second-cousins that I hadn’t seen since grade school suddenly felt like I owed it to them, because we’re family, to pay off their student loans or buy them a new washer, or whatever. My great-aunt (my maternal grandmother’s sister), who I saw once a year at most, sent me an urgent plea for bail money for her son, who had been in and out of jail his whole life. I didn’t see the urgency, so I didn’t send her anything, for which she ripped my mother a new one. The pleas for cash would taper off after a few months, once these relatives realized that I wasn’t going to subsidize them. I got probably two dozen kiss-off letters from various second cousins, third cousins, friends of the family, and so on, congratulating me on my newfound snobbery and wishing me a good time in Hell.

I didn’t think it was snobbery at all. For one thing, had one of my second or third cousins, or even one of my first cousins, suddenly come into a bunch of money, I wouldn’t have dreamed of asking them for some, or any, of it. And for another, regardless of how many zeroes I had in my bank account, I didn’t believe it was my place to subsidize their lives. I was genuinely hurt that they took it so personally when I wouldn’t help them. One of my second-cousins, especially, really hurt me when he swore off contact with me. We were about the same age and saw each other a couple of times per year. When we were kids, we weren’t friends, by any means, but we played together and got along. When he sent me an obscenity-filled tirade telling me that I was urinating on our family for not sending him twenty thousand dollars to fix up his house, it actually kind of stung. I never did send him any money, though.

Once we had finished writing checks, throwing away kiss-off letters, and exploring Miami, Caitlin and I pretty quickly ran out of things to do. Had I known any better, I would have found something meaningful to occupy my time, be it charity work or whatever. But I was rich, and rich people do as they please, so I resolved to not do anything that would put any demands on my time. Worse still, I started to crave that high I first had when I read the winning lottery numbers a few weeks earlier. And even though it only was a few weeks earlier, it seemed like several lifetimes ago.

CHAPTER 4: EVERYTHING GOES WRONG

By Christmas, being rich had become rather boring. Watching Jerry Springer all day in a high-tech media center in a beachfront mansion is really no different from watching him in an apartment, after the 400th time you’ve watched him. Even the beach had gotten tiresome – after all, it was the same ocean day after day. Caitlin and I spoke vaguely of traveling to Europe or Australia or somewhere, but we never got around to applying for passports. South Beach had run its course the day we checked out of our hotel. Even Little Havana had become passé, and we only went a couple of times per month by then.

One weekend, we decided to go to New Orleans. My mother had been there several times and had recommended it to us. Since we were desperate for something to do, we booked a flight and got a hotel room in the French Quarter. The night we arrived, we showed up at Antoine’s, where we had supper reservations. Although the food was exquisite and the service polite, it was obvious we were second-class citizens from the moment we set foot in the place. Even though it wasn’t very busy, we were given a seat back in a corner, even though there were several tables by the window, allowing for a view of the street. The waiter never did offer us a wine list, instead just bringing us ice water every time our glasses got low. And apparently they were “out” of Oysters Rockefeller that night, despite the fact that several other diners got plates of what looked like oysters covered in creamy sauce. Later that night we were in Pat O’Brien’s discussing this experience with some locals, who told us that the Maitre d’ at Antoine’s has an eye for who has Old Money and is from New Orleans, and if you don’t meet both standards, he instructs your waiter to get you out as quickly as possible.

Following my New Orleans experience, and considering what had happened at South Beach, I developed the theory that, in certain parts of the country, having a lot of money means very little if you don’t have some other attributes to back it up. On the East Coast, unless your name appears in the Social Register, forget joining that country club, even if you can afford the dues several times over. In the South, particularly in New Orleans, unless your money goes back for several generations, you’re just another tourist. And in parts of Miami (and, I would assume, parts of most other trendy U.S. cities), having money is great, but unless you’re young and beautiful, no one has much to say to you.

That first Christmas was a perfect metaphor for how bored we were. Neither Caitlin nor myself could think of anything, anything at all, to get for each other. We both had everything we wanted, and plenty of stuff we didn’t want but that we just wound up with anyway. Her closet was filled with new clothes and designer shoes. I had every CD and DVD that had ever been produced, it seemed, not to mention every top-of-the-line gizmo that Best Buy or Sharper Image had to offer. What do you get for the person who has everything they want? I wound up getting Caitlin a $5,000 diamond ring, even though she was a low-key girl who didn’t much go for bling, but I couldn’t think of anything else. She bought me a personal watercraft, but since it was winter (by Miami standards) the water was a little cold so I couldn’t use it right away.

It was becoming apparent that Caitlin and I had much different interests. I had started indulging in my passion for NASCAR races, flying off to Talladega or Atlanta every weekend, and throwing around enough hundreds until I wound up with front-row seats and limitless free beer. Caitlin went with me the first few times, then proclaimed that she had no real interest in NASCAR, and bade me a good time on future trips without her. If Caitlin minded being left home alone while I flew off to another state every weekend to watch men make left turns, she didn’t show it. And unlike New Orleans or South Beach, NASCAR venues seemed glad to have me there.

At one NASCAR event, I believe it was in Charlotte, I somehow managed to get escorted to a backstage area. There I met some pit crew personnel and a few drivers, none of whose names I recognized. I also got to go to a “special” gift shop, one apparently reserved for VIP’s. The regular NASCAR gift shops have NASCAR towels, NASCAR T-shirts, and all manner of other NASCAR gewgaws. This “special” gift shop had authentic, signed memorabilia, and the coup de grace was a jumpsuit that had belonged to one of NASCAR’s big names from its early years. I bought it, for $15,000. When I got it home, I added it to one of our home’s four bedrooms, which I had dubbed the “trophy room.” The “trophy room” was going to contain all of the sports memorabilia, most of it NASCAR, that I would acquire, and then I’d hire a designer to arrange it all attractively. That never happened, and the jumpsuit wound up hanging in a closet, over boxes of other NASCAR junk that I’d bought.

I also tried to indulge my passions for football and baseball, though in Miami my options were pretty limited. I bought my way to good seats at a couple of Dolphins games, but in reality, it’s much easier to watch an NFL game on TV than it is in person, considering all of the replays, the different angles, and the speed of the action. Baseball in Miami was a total bust. My favorite team was hundreds of miles away, and when they played in Miami, they played to a stadium with half of the seats still empty. The atmosphere was nothing like the packed houses, full of electric fans, at my team’s home stadium. Even I, spendthrift that I was, knew that flying all over the country for Major League Baseball games would be too expensive, even for me.

I had stopped speaking to my family by this time. Well, more accurately, they had stopped speaking to me. I had paid off my brother’s mortgage and the car loans on both his and his wife’s car. Without a mortgage payment, my brother figured he could afford the payments on a new Hummer, so he traded in his car and bought one. Trouble was, he couldn’t afford to keep gas in it AND pay the insurance premiums on it, too. So he stopped paying the insurance premiums. Naturally, the bank took a pretty dim view of this, and they repossessed his Hummer. He called me asking me to pay to get his Hummer out of the repo yard and pay his insurance premiums for the year. I told him I would do no such thing, and that I wasn’t going to underwrite his stupidity. He called me a name and I hung up. An hour later my mother called, lecturing me about how badly I had treated my brother, how I had let money cloud my judgment and get in the way of my relationship with the family, blah blah blah. I tried to plead my case, but Mom wasn’t hearing it. After much continued arguing, she told me that she couldn’t continue to consider me her son if this is the person that I had become. And that was it. I haven’t heard a word from her to this day. And since Mom stopped speaking to me, so did my stepfather. And since my stepfather wasn’t speaking to me, neither were my other siblings.

I had also fallen out with my dad, in a much more dramatic fashion. I had paid off his mortgage and, since it was nearing maturity anyway, decided to buy him a new truck and buy a new car for his wife (she opted for a Chevy Suburban SUV). One day about two weeks after I did all this, I got a frantic call from Dad’s wife. She said he was “in trouble” and needed a hundred thousand dollars. Stunned, I asked what my father could have possibly done to get into the kind of trouble that required a hundred large to get out of it, but she wouldn’t say. I pressed her on it, but still got nowhere. My dad smoked quite a bit of pot, but not enough to catch the attention of the police, not to the tune of a hundred-thousand-dollar bond, anyway. He certainly didn’t deal. He didn’t have any use for any other drugs; wasn’t involved in any kind of crime; and didn’t have any kind of gambling or other problems that I was aware of. Still, his wife wouldn’t fess up. I told her that until I knew what was going on, I was going to have to say no. She called me a name and hung up. That was the last I heard from her or my dad. He wouldn’t return my calls, and I stopped trying after a couple of weeks.

Caitlin and I were starting to not get along, either. I was spending my weekends jet-setting, as much as one “jet-sets” while going to NASCAR races, and spending my weekdays vegetating in front of the TV or driving around town, looking for something to amuse me. Caitlin had wanted to use our money to make something of an ordinary life for us. She made it clear that it was time for us to have kids. She had even gone so far as to look at brochures of area private schools, even though it would be six years before a child of ours saw the inside of a school, even if we got pregnant that very night.

She also wanted us to have constructive things to do. We had spoken obliquely about buying our way onto some non-profit boards or doing some kind of charity work. Caitlin had grown up with a cousin with Down’s Syndrome, and was interested in us maybe working with the Special Olympics in the Miami area. My belief was that the $50,000 check we sent to Special Olympics was more than enough to satisfy whatever perceived debt of honor Caitlin thought we owed them. Caitlin saw it differently, and said she had better things to do than waste away in front of the TV. We argued every night about my lack of motivation and direction. She took it as a personal insult that I was waiting for her to make something of her life while I chose to be a layabout. I took exception to the word “layabout,” even though it described me perfectly. Our arguments got more frequent and more serious.

When Miami’s cultural offerings had run their course, and I had tired of daytime TV, I started spending my weekdays gambling. Perhaps out of boredom, I started trying to re-capture that rush I felt when I first won the lottery. Miami has no shortage of ways for you to gamble – there’s horse racing, dog racing, jai-alai, and if that’s not enough, cheap flights to Nassau and its Bahamian casinos. There was also the nearby Hard Rock Seminole Hotel & Casino, which didn’t require an international flight.

I was quite the high roller at the Hard Rock. When I was at the tables, the booze flowed freely. I tried to temper my drinking, since I wanted to have all my faculties when I worked the tables, but on more than one occasion I wasn’t sober enough to drive home, and the pit boss was more than happy to comp me a room. After about the fifth time this happened, I stopped bothering to call Caitlin to tell her I’d be gone all night. Then I’d feel guilty and drive home the next morning, long enough to pretend to want to be home, before I headed back to the Hard Rock, or a race track, or wherever.

I got quite comfortable at the sports book at the Hard Rock. In addition to betting in baseball, football, and all manner of other sports, there was horse racing. The interesting thing about betting on horse racing at a sports book is that, with simulcasting of several tracks around the country, there was action every couple of minutes. Horse racing offered me the chance for big wins – correctly pick a superfecta, even on a $1 bet, and you could be in the tens of thousands. The sports book offered a sense of privacy, which, believe it or not, I found unsettling. You could, conceivably, spend several hours at the sports book, winning and losing thousands (or tens of thousands), without ever speaking to a real person. Program your bet on the computer terminal at your table, swipe your credit card, and watch the event on your screen. If you win, credit your account or print a slip and take it to the window. If you lose, thanks for playing. I spent my share of time at the sports book, to be sure. But the solitude would wear on me, and I usually only went there when I got bored, or got on a huge losing streak, at whatever game-of-the-week I was into.

When horseracing would run its course, I would head for the blackjack tables. Most nights, when I hit the blackjack tables, I’d withdraw $10,000 at the window, on my credit card of course. Split up into hundred-dollar chips, that netted me 100 chips. I could make those last a few hours, before I’d be too sleepy, or too drunk. Some nights I’d win, or at least, I’d break even. Most nights I’d lose – a thousand here, five thousand there, sometimes all of it. When I didn’t lose I’d have the remainder credited to my card – like I’d learned to do in Vegas.

Playing $5 or $25 hands at the blackjack tables is the purvey of college students, weekend tourists, and old men. Playing $100 hands at blackjack, at least in Miami, gets you a lot of attention. In addition to the free booze and the casino host falling over you, you become a sort-of mini celebrity. I loved it – the rush that you get when you turn over an ace to a king upcard is exciting, but it’s magnified a hundred times when a crowd cheers along with you. More often than not, that crowd included attractive young women. Women who viewed me as a rock star – or at least, as the best thing going in the casino that night. Women who didn’t bug me about getting a spot on the board of the Special Olympics.

The first night I cheated on Caitlin, I at least had the decency to feel guilty the next morning. My room had been comped, as had happened dozens of times, and when I woke up I realized there was a woman in my bed. I wanted to throw up, just from the guilt. The night had started out somewhat innocently – she was in the crowd watching me play blackjack. Eventually she struck up a conversation: where was I from, yada yada yada. It felt good to talk about something other than my shortcomings. I was on a winning streak, so I cashed in my chips and invited her over to the bar for a drink. Seven or eight tequilas later, we were in my room.

I headed home the next morning, all the while formulating a plan to make it look as if nothing had happened. For whatever reason, there was no need for a plan. Since overnight stays were almost a twice-weekly occurrence by this point, Caitlin didn’t think anything was amiss. She was, however, quite concerned about my $90,000 credit card bill that had arrived in the mail the previous day. I told her I’d pay it, and it wasn’t like we had to watch our spending. Apparently I was wrong, because Caitlin burst into tears. She said I had a gambling problem and was going to bleed us dry. The last thing someone with a gambling problem wants to hear is that they have a gambling problem, so I made some excuse to leave.

To this day I don’t know how it was that Caitlin learned I was cheating on her. There were other mornings when I woke up with women in my bed, and after the third or fourth time I stopped feeling guilty about it. I don’t know if Caitlin had hired a private investigator, or if she simply put two and two together. All I know is that I went home from the casino one morning, and Caitlin was sitting at the living room table. She merely asked if I was cheating on her. I didn’t feel like lying – it would have taken too much energy – so I simply said “yes.”

I’ll never forget the look on Caitlin’s face. If a single facial expression can convey both shock and relief, she managed it. Shock that the man she loved had cheated on her, and relief that she finally had an excuse to divorce me. Doubtless she had been thinking about it for some time – I was no longer the man she fell in love with and married. Now that she had a reason to leave, she was probably glad. Without a word, she turned around and went to our bedroom to pack. I didn’t follow her. A while later I heard the garage door open, and I heard her Lexus start up and then leave. I never saw her face-to-face again. The next thing I heard from her was through her lawyer.

No unexpectedly, Caitlin had filed for divorce. What was unexpected were the words “child support” on the divorce petition. Apparently during our months of fighting, Caitlin and I got along well enough on at least one night to make love, and she was pregnant. I knew the baby was mine. Unlike me, Caitlin wouldn’t cheat.

The court proceedings were amicable. I didn’t feel like fighting Caitlin on any point in her divorce petition. She at least had the decency to ask only for what was fair. Unfortunately, the judge had a different idea of what was fair than either of us had in mind. He ordered the balance of our liquid assets split down the middle. That was relatively easy – our money just sat there in a checking account. A heavily-insured checking account, to be sure, but a checking account all the same. The judge also informed me that I would have to either sell the house and split the profits with Caitlin or buy out her share – I chose to buy out her share. I also had to buy out her share of the house’s furnishings, of which her lawyer had made a meticulous account. One of the items on his ledger was my $15,000 NASCAR uniform. Caitlin hadn’t bought it, had no interest in it, and probably hadn’t even looked at it since I first showed it to her, but nevertheless her lawyer thought it only fair that I pay her for half of it, and the judge agreed.

All in all, my divorce cost me about six million dollars. If that wasn’t bad enough, the judge had ordered me to pay child support to the tune of $4,000 per month, beginning the following month (pre-natal care, apparently). He used the words “lifestyle to which she’s become accustomed.” I don’t think Caitlin herself asked for that figure – I don’t think she wanted any child support at all, really. But the judge did not suffer fools, or adulterers, lightly, and he made sure I paid the price.

The day our divorce was final, my bank account was about $3,400,000 in the black. The interest borne on that account was about $140,000 per year before taxes – a healthy income by just about any standard. However, $48,000 of that would go to child support. Another $30,000 would go toward property taxes. About $9,000 went to insurance – both on the house and on my Viper, which required premiums in the neighborhood of $350 per month. Homeowner association dues, utility payments, and other here-and-there bills would add up, and I was living well beyond my means. Even if I didn’t have a gambling problem, each year I would be eating into my remaining principal.

With Caitlin out of the way, I was free to gamble with impunity. I think that, in the back of my mind, I was aware that I was going to go broke, and quickly. I gave myself a self-imposed limit of $5,000 per night (instead of $10,000), and I stuck to it, for the most part. Most nights I would stop when I was just buzzed enough on free liquor that I didn’t want to drink any more lest I couldn’t drive home. I’d take my losses, or my winnings, and call it a night. Of course, most nights I was behind, but nights when I lost my whole limit were, mercifully, rare. Either way, I would go home comfortable in the knowledge that I could come back tomorrow. After all, I was a multi-millionaire. And I always knew that I was two or three consecutive superfectas away from adding a few more million to my account. This would go on for the next three years, which now are mostly a blur.

Not many Americans ever get a chance to bounce a check for $123,981.87. Heck, not many Americans ever get a chance to write a check for that amount of money. But one day I opened up my mail and got the overdraft notice from my bank. I certainly hadn’t expected something like that to happen – after all, I was a multimillionaire. Nevertheless, millionaire or not, my credit card company expected me to pay the bill, and when it bounced, they weren’t amused. I went to my bank to see what had happened.

My bank had had surprisingly little to say to me when I was rich. They had even less to say to me when I was broke. When I initially opened my account, the teller didn’t bat an eye when I told her a wire transfer would come through, with my initial deposit being about fourteen million. There were customers at my bank for whom fourteen million was a drop in the bucket. My fourteen million dollar account had about two thousand in it, which was not enough to cover my credit card bill, not by a long shot. To make matters worse, my taxes were going to be due – the interest that my account had earned, which I had blown at the tables, was taxable income. And the worst problem of all, as I would find out, was that I didn’t have enough to make my next child support payment.

I found out just how big a problem this was when a pair of sheriff’s deputies showed up at my door with a pair of handcuffs and put me in the clink for Contempt of Court. The judge seemed to take it as a personal insult that I didn’t pay my child support payment that month, as ordered. The fact that I had put myself into a position where I couldn’t pay it if I wanted to bought me no sympathy – if anything, it made him even madder. He set a bond for me – a bond! – and warned me strongly against trying to leave the county. Then he set a hearing for thirty days from then, in which he would determine how my assets would be liquidated to satisfy my child support obligations.

I hired a lawyer. His advice was pretty straightforward: “For the next thirty days, you are the judge’s bitch.” He told me to not so much as pawn a CD or the judge would throw me in jail for fraud. He made me give him my credit card, and he froze my checking account. For the next thirty days, I had to literally ask my lawyer for gas money, and then show him the receipts. Even though I desperately wanted – needed – to get back to the tables, the knowledge that I could go back once this legal business was over got me through. Another thing that kept me in line was the fact that, if the judge suspected any kind of shenanigans on my part (such as hiding or liquidating assets, etc.), I would have gone straight to jail, where I would have literally been someone’s bitch. I spent most of my time sitting on the beach – I figured my days of being able to do that were coming to an end, so I decided to make the most of it. For once I was glad that my neighborhood was boring – the last thing I wanted was to have to talk to any neighbors.

Canceling the maid service was hard. Even though I’d said nothing more than “Buenos Dias” in four years to our maid, I’d grown attached to her. Nevertheless, since I couldn’t pay her salary, she had to go. Canceling the lawn care service was even harder. The owner didn’t want to lose my business, and was pretty adamant about keeping me.

“Could you tell me why you’re canceling?”

“I’m moving.”

“Well that’s no problem. We can transfer your account to another address. Just let me get a pen and paper…”

“I’m moving to an apartment.”

“Well who’s your condo’s management company? I’m sure we can do a better job of maintaining the grounds then whatever their guy is doing.”

“No, I’m moving to an apartment.”

Silence. Then, “Oh. I see. Well, thanks for your business.” Click.

The judge looked over my spending habits, my assets, and my liabilities, and decided that there was nothing better to do than to auction all of my belongings. My debts would be satisfied first, then whatever was left, minus my attorney’s fees and some percentage to be given to me, would go to Caitlin, to satisfy the child support obligation. The auction was to be in another thirty days, which meant another month of staring at the water, begging my lawyer for gas money, and worst of all, longing for the tables.

The auction brought out all manner of repo men and people who make their fortunes selling other peoples’ possessions that they no longer deserve. I recognized the names on some of the trucks – foreclosure management companies, furniture wholesalers, etc. There was even a guy I recognized from a baseball card shop I’d been to once; apparently he read the words “sports memorabilia” in the auction notice. Too bad for him that my “sports memorabilia” consisted of two boxes of NASCAR gewgaws – boxes that had sat unopened in a closet for four years, and which he bought, along with the $15,000 jumpsuit, as part of a lot for $400.

To say that the auction was the worst day of my life would require me to actually have felt emotions that day. I felt none – actually, I was numb. The experience of watching everything that, at one time, had been important to me get hauled away, was not an experience that my brain could even process. Even when my beloved Viper was towed away, my brain rationalized the experience by remembering that the suspension on it was so tight that I could run over a watch and tell you what time it is. My painting from Little Havana, my LCD TV, my media room equipment… just about everything but my clothes and my CD’s were sold and hauled away.

After all was said and done, and I paid off my lawyer, I wound up getting a check from the county for $49,437.33. At that very second, I had the first moment of sense that I’d had in years – I ignored my first instinct, which was to rush to the casino. Instead, I took a bus to my bank, deposited the check, and kept out a few thousand dollars in cash. I took a bus to a car lot and bought a used car for $5,000 – a Ford Taurus – and then went to a used furniture store and bought a sofa, a bed, etc., and told them I’d call them later with the address to deliver it to.

Then, I went and put down a deposit and first month’s rent on an apartment. The place I wound up renting from was built in the 60’s, and it showed. It was called “The Gables,” or somesuch, and ostensibly it was supposed to evoke images of a castle in King Arthur’s day. It looked more like an appalling mess of brown and yellow paint. The neighborhood was expensive enough that it kept most of the riffraff out, and could be considered reasonably safe, but still cheap enough that I could afford the rent. I knew that would be important, because my next step was to find a job.

With $50,000, I could have bought outright a mobile home, bought some land to put it on, and lived comfortably on a lab technician’s salary back at my hometown in the Midwest. In Miami, $50,000 wouldn’t get you a down payment. Still, I decided that being homeless (if it came to that) in Miami was better than living in a trailer in the Midwest, so I decided to stay. Besides, I had big plans for my remaining money.

Employers don’t look too kindly on gaps in one’s work history – especially if that gap is longer than a few months. They want to know what you’ve been up to, and if your answer isn’t satisfactory, you won’t get the job. A gap of four years screams “prison sentence,” and my explanation that I’d spent the last four years gambling away fourteen million dollars wasn’t going to endear me to any employers, either. I got a few interviews at various hospitals, and hemmed and hawed when the inevitable questions came up. I tried to convince the interviewers that I was just taking some time off, and that I’d saved up enough money to be able to do so, but they weren’t buying it. This went on for several weeks until, in desperation, I called my old boss at the lab. He wasn’t interested in talking to me, but I offered him to wire him $10,000 if he’d promise to lie and say that I’d been working at his lab for the past four years. He agreed, and I guess his lies worked, because a week later I got hired on the 3-11 shift at another lab, in a hospital about 15 miles down the road.

I went to my landlord’s office and paid, in cash, six months’ rent in advance. He didn’t ask why, but I made sure he gave me a receipt. Then I filled up my gas tank, went to a grocery store and bought two weeks’ worth of food, and then headed for the casino.

I took a seat at the sports book and looked over the day’s races. I picked a superfecta that looked good. Three different handicappers had all agreed on which four horses were going to finish in the money. All in different orders. I bet $1,000, and boxed it, which meant I wagered $16,000 on the race. If I had won, I would have made a couple of million, for which I had plans for my next bet, and my next bet after that, and my next bet after that, and so on. I didn’t win; two of the horses didn’t finish in the money.

With my last $16,000, I picked another superfecta. A thousand dollars, boxed sixteen ways. I had read the handicappers’ reports on the internet and on the racing form. There were three clear favorites, and the fourth could go either of several ways. I made my choice, and laid down the bet. Another bet that would have brought me millions, which I would use to finance my next superfectas. The cashier didn’t bat an eye – he watched me count the money, then he put it in his drawer and handed me a ticket. Three of the four horses finished in the money. The fourth lost by half a length.

I went straight to a pay phone and dialed the number for problem gamblers in Florida, which casinos are, presumably, required by Florida law to display. I didn’t even have the thirty five cents to make the phone call. Fortunately, it was a toll-free number.

CHAPTER 5: PICKING UP

“My name is Aaron, and I’m a gambling addict.”

“Hi Aaron.”

“In the past four years, I’ve gambled away fourteen million dollars. This time a year ago, I lived in a mansion on the beach and drove a Viper. Now I’m living in an apartment that’s about the size of my old bedroom. I’ve gotten divorced from my wife. I have a son that I’ve never seen. I don’t speak to anyone in my family any more. Just about all I have left is a used car and six months’ rent credit on a crappy apartment.”

I expected to get some kind of award for having the juiciest story, or at least most interesting story. I was wrong. The meetings had no shortage of riches-to-rags stories, to be sure. Then there were the guys who missed their mortgage payments and their families had to go to a homeless shelter. There was the guy who got in with a loan shark and had his knees broken. There was the woman who sold her baby’s formula to a crack dealer so she could buy lottery tickets.

They say that addicts have to hit rock bottom before they admit they have an addiction. My rock bottom was when I missed out on a million-dollar payout by a few thousandths of a second and had to go to work the next day. Truthfully, I got off light. No one went hungry because of me.

I literally ached at not being able to go to the tables. My chest hurt. My stomach churned. Sometimes I could barely breathe. My daily meetings gave me some kind of motivation to not pawn my belongings or blow my paychecks at the tables; where that motivation came from, I’ll never know. Shame? Guilt? A Higher Power? 12-step program or no 12-step program, I was still broke, and no better off than I was before I got rich.

One night at the lab, I sat there at my desk and had a moment of clarity. The phone was ringing off the hook, and all around me sat samples, each more urgent than the one next to it. I ignored the phone, closed my eyes, and imagined myself injecting myself with blood from one of those samples. I knew which one had hepatitis. The pain, the shortness of breath, the indescribable mental cravings – it would all be over. Trouble was, hepatitis is a painful disease that kills you slowly over the course of several years. But I already had a disease like that – addiction. I went back to work.

It was at the lab that I learned the secret of why I was unable to order pizza when I lived on the beach. One of the lab assistants on my shift had worked for a pizza place, and he told me the story. He also told me that he made twice as much money delivering pizza as he did at the lab. But he liked The Sauce, and he got a DUI, which will instantly end your career delivering pizza. He also showed up at the lab one night with liquor on his breath, and failed the breathalyzer, and was given the pink slip from the lab. For all the drinking that I did, and trust me, I did a lot, I never did develop a drinking problem. For that I am grateful. Even today I could get bombed and then go back to work tomorrow like nothing happened. But give me an instant-lottery ticket…

One of the 12 steps in a 12-step program is to make amends with everybody you’ve ever wronged because of your addiction. That proved relatively easy. My mother, my brothers, indeed everyone on my mother’s side of the family, had changed their phone numbers. I sent mail to their last known addresses that got marked “Return to Sender.” My father still wouldn’t return my calls. My old boss was forgiving, although I think that the $10,000 I’d sent him a few weeks earlier helped.

My old father-in-law, Roger, was the hardest call I had to make. I expected him to give me the third degree for what I’d done to his daughter. Surprisingly, he was understanding. We talked for over an hour. At the end, I felt like I had poured out my entire soul to him; we spoke of how, when I first visited his home back when I was a junior in college, I was jealous of his garage, his pool, his fireplace – all the things that my home as a kid lacked. We spoke of how all the wealth, all the things I thought I wanted, or needed, didn’t fill the void I had. We spoke of how I had treated money as a tool simply to be misused. We spoke of the biggest thing that he and I both had in common – our love for Caitlin.

Roger wouldn’t give me Caitlin’s number, of course. But he did promise to tell her what was going on and to try to convince her to call. I didn’t expect her to, but she did, a couple of days later. Our conversation was civil – Caitlin couldn’t be rude if she wanted to. I think she genuinely felt sorry for me, though any love that she had for me had withered and died. She was remarried, and living in a nice home in a suburb near where her parents lived. The interest that she earned from her divorce settlement enabled her to be a stay-at-home mother, which was all she ever wanted. I wished her the best.

One day, I went back to Little Havana for old time’s sake, and stopped by the art gallery where Caitlin and I had bought that favorite painting of the Cuban fortress at sunset. I looked at all of the artist’s beautiful paintings and admired her work. Of course, buying one was out of the question.The artist actually remembered me, which was surprising. We struck up a conversation about what had gone on the past few years – the divorce, the painting going to Caitlin (I lied; it had actually been sold off), etc. I didn’t mention the money, of course. I learned that the artist’s name was Maribel. Then she did something that stunned me – she offered to paint me another painting of the fortress, for free!

“I couldn’t possibly ask you to do something like that,” I said.

“Is nothing. We are friends. That’s what Miami is: ‘Mi ami – mi amigo. My friend.’”

“I appreciate the offer, but-“

“Hey amigo. When a Cubana grandma offers you a favor, you no turn it down, OK? Back in Havana abuelas like me we get respect, no? I make you painting. You take it. OK?”

On the way home, I stopped by an art supply store. I have no idea what motivated me to go there – it was almost like the Universe was taking me there. I had just gotten in my car and started driving, and the next thing I knew I was pulling into the art store’s parking lot. I bought a canvas, easel, palette, and some paints and brushes. Back at home, I got on the internet a found a photo of a woman wearing a red dress, and standing on a balcony of some mansion somewhere. By the style of the dress and the woman’s hairdo, I figured the photo came from the 1940’s. I set up my easel next to my laptop, and set about to painting the woman and her dress, only I made the dress purple. I ignored the background and concentrated only on the woman. I had no real idea of what I was doing, but 12 hours later I realized that it was time to go to work!

A week later I returned to Maribel’s gallery in Little Havana. I had brought my painting of the woman in the purple dress, wanting Maribel’s critique of my artwork. Maribel gave me my painting that she had made just for me. It was smaller, of course, maybe seven inches long by five inches high. In the bottom right corner, with a very fine brush, Maribel had signed it. “To Aaron. Mi ami, 2006.” I understood that by “Mi ami” she meant “my friend,” and not Miami, the city. To this day, I keep the painting on my desk at the lab, as a reminder of what was fun and beautiful about those years.

Maribel was impressed by my painting. She critiqued some flaws here and there, but told me that I had real potential. She gave me the names of some artists she knew who gave lessons. Then she gave me $400! “You no tell nobody ‘bout this, OK? I sell Maribel’s painting, not no Anglo’s.” I went to my bank to deposit the money – it would be enough to cover a few weeks’ worth of classes at one of Maribel’s colleagues’ art class. As I stood in line to deposit the cash, it occurred to me – I hadn’t once thought of going to the casino and betting the money. I knew, finally, that I was going to beat this thing.

These days I’m still working at the lab on the 3-11 shift, and still living at The Gables. I’ve painted a couple dozen paintings, and Maribel has sold a couple of them, although she still insists that I keep quiet about it, lest every other wannabe artist in Miami start flooding her with their cacotas, as she calls inferior artworks. I spend my days off at the beach – public beaches, of course. Now that I don’t live on the beach any more, it appeals to me again. I still attend Gamblers Anonymous meetings, twice a week now instead of daily. Caitlin and I don’t really speak any more, which is probably for the better. Our son has a dad, the only dad he’s ever known, and if I were to make my presence known it would probably just confuse him. I’ve driven by the old neighborhood a time or two, but I haven’t tried to get past the guard station (the guard probably wouldn’t let me past, anyway).

I learned through Gamblers Anonymous that my identity is not tied up in any one thing. I am not singularly a gambling addict, a lottery winner, a lab worker, an apartment dweller, an amateur painter, a college graduate, a divorcee, an absentee father, a writer. I am a conglomeration of all of those things, good and bad, and the whole is greater than the sum of its parts. For better or for worse, this is the hand I’ve been dealt, and it is no one’s to play but mine; one day at a time.

Big Daddy Homie

Saturday, April 10, 2010

How Far Is It To Branson?

Monday, July 7, 2008

Novella

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