The Smart Money: How the World's Best Sports Bettors Beat the Bookies Out of Millions

Introduction

November 2000

The Western Tanager calls Central America home, but during its annual migration observant bird-watchers can spot this little beauty in the most unlikely locations—even in the densely populated hills rising above the industrial cacophony of Sunset Boulevard, in Hollywood, California. You don’t have to be an expert ornithologist to notice the Tanager. It’s canary yellow, with a brilliant red head that looks like the logo on the helmet of the Phoenix Cardinals. It has a black back, like the home jerseys of the Jacksonville Jaguars. And one white and one yellow wing bar, a design that no NFL team has yet co-opted. When it’s not breeding, it lacks the glowing cap, and the bird books say that in this state it’s common to mistake the Tanager for a male American Goldfinch or a female Bullock’s Oriole—which is what I must have done, I tell myself. It’s nearly Thanksgiving; any Tanagers that once nested here in the palms of Los Angeles must be currently enjoying the tropical sun down in Costa Rica, where, along with dozens of species of tree frogs, butterflies, and serpents, many of the world’s biggest bookmakers permanently reside.

Still, the flash of yellow and orange outside my living room window catches my eye, and that’s not easy to do when football is on the television. The antics of the brightly colored gladiators, heavily muscled warriors outfitted as gaudily as macaws, seem to matter to me more than to the average sports fan. Actually, at this point in my life I no longer care about the interstitial running around and tackling, the passing and catching, the playing of the game. I’m concerned only with the little box in the corner of the screen, the one that shows the score.

I brush aside a pile of papers on the coffee table, a stack of spreadsheets with numbers on them that I barely understand, and I grab my binoculars. I use them to spot the green parrots (pants of the Miami Dolphins) and Western Scrub Jays (Minnesota Vikings), and the dozens of hummingbirds and finches that flit around the gardens of my house. I’m not really a birder. I don’t maintain a life list or spend my vacations in Louisiana swamps searching for rare species of woodpecker. But I do enjoy looking at the winged creatures around the neighborhood. Observing their grace and beauty gives me a sense of peacefulness, a calm, that most of my waking hours sorely lack. When I pick up my field glasses, I’m momentarily transported to a tranquil sanctuary, where some of Hollywood’s biggest movie stars aren’t calling me to scream about their investments. Where no one cares about the supercomputer I’ve got stashed in a Massachusetts apartment. Where it doesn’t matter what legendary gambler is on my speed-dial.

If an uninitiated visitor wandered into my living room, he would observe what seems to be domestic normality: the dog asleep underneath the piano, the TV flickering in the corner, the late-afternoon sunlight streaming through the large picture window, the man in his thirties attired in a sweatshirt with cold pizza stains on the sleeve. Few would guess that this modest Hollywood bungalow is the home of a serious professional gambler. I’m the owner of the house and I can’t believe it. Just three years earlier I was an earnest middle-class American, a writer searching for a good story.

I found it.

It was hidden between the lines, enmeshed among the Las Vegas point spreads and betting odds, like a sparrow camouflaged in bougainvillea vines, almost invisible until you look more closely, with a telescopic visual aid or an expert teacher.

The New York Giants and their 4-point lead over the Washington Redskins can wait; I’m determined to positively identify the wayward Tanager I think I’ve seen streaking past my window. I raise the binoculars to my eyes and scan the trees across the street. It’s all an emerald blur. I focus. The individual branches come into view, but no birds. Wait, there’s something! Oh, just a dove. No sign of the lurid yellows and oranges that signal toxicity to predators but look so fine to our human eye.

I put down the glasses and scan the street with naked eye, hoping for a burst of color, some frantic movement. Everything is static. I see houses built on granite bedrock, noble firs unruffled by wind, parked cars. Nothing animated.

Then a glint of light twinkles from across the way. I bring the lenses back to my eyes and look for something moving. Slowly, like the establishing shot in an epic western, I pan from the left side of my quiet residential street to the right. Stalks of bamboo. A cypress tree. Pink impatiens. The pavement on my neighbor’s driveway. A white picket fence. A Buick.

A Buick with a balding man slouched low behind the steering wheel. Looking straight at my front window. Through binoculars.

I pull the magnifiers from my eyes to see the big picture from a normal perspective, because, surely, the pressure of the past year has started to get to me and I must be seeing strange and troubling things.

Before I can get another peek at the Buick’s occupant, the car roars away, its tires screeching like a flock of parakeets.

I run out my front door, down the steps, and out to the sidewalk. I look up the street. Nothing. He’s gone.

None of the neighbors seems to be around, and if any are, they’re staying inside their home with the shades drawn, safe from spying interlopers. I feel alone, as though I’m the only living person in a ghost town, with only my dog and a tangle of increasingly frightening thoughts to keep me company. My impulse is to lock myself inside the house and phone my mentor and protector. But before I make the call, I entertain an even more disturbing notion: perhaps he’s the one having me watched.

I trudge back to the living room. The Giants have widened their lead to 7 points. My famous colleague Captain Beefcake, who ought to be worrying about the box office numbers of his new thriller and not the score of a meaningless NFL game, has left what is probably an irate message on my voicemail. And the birds, the ones I’ve seen and the ones I suppose I’m only imagining, have left the feeders and returned to their nests. The only creature to watch, it seems, is me.

I close the curtains and double-bolt the door. Then I squeeze into a corner of the couch, cover myself with a wool blanket, and wait to see if Washington can make a late score.

One

A Proposition

June 1997

Rick Big Daddy Matthews and I are playing golf at the Sherwood Country Club, not far from his summer home near Santa Barbara, California. Founded by David Murdock, the gentleman who owns Dole and much of the island of Lanai, the club is a rarefied playground where some of the most privileged people in America dig up the sod. The clubhouse is the size of a respectable basketball arena, albeit one outfitted with leather furniture and a staff of full-time shoe-shiners. Tiger Woods has his annual postseason invitational here. This Sherwood isn’t the kind of place where ordinary Robin Hoods might enjoy a game of golf. Initiation fees are reportedly more than $250,000, an impost that ensures that the first tee remains accessible to the celebrity membership, which allegedly includes Jack Nicholson, Kenny G., and Janet Jackson—although discretion prevents the club from commenting on such delicate matters.

Rick Matthews moves comfortably in these elite circles. A millionaire many times over, he’s built a four-state empire of casual gourmet restaurants, where patrons pay premium prices for a fine dining experience uncomplicated by menus written in French. He has all the trappings of extraordinary financial success: a private jet, a fleet of luxury cars, and a stable of mansions (some of them with actual stables). Big Daddy gives generously to charities, to institutions of higher learning—which courteously rename academic buildings in his honor—and to politicians who are sympathetic to his concerns. The man is a vital member of society.

And he got where he is by taking a gamble.

Actually, thousands of them.

The restaurants, the mansions, the ear of the senator—the whole towering monument to the American dream is built on a foundation of bet making. Not wagering on the stock market or an obscure foreign currency, but the kind of gambling most citizens of the United States can vaguely understand from firsthand experience. Big Daddy Matthews made his fortune betting on sports.

The man has always had a penchant for games of chance. For taking a risk, even a foolish one. Before becoming the kingpin of American sports betting, he won and lost millions of dollars on roulette, blackjack, and other negative-expectation casino games. At one time Rick Matthews, son of a church deacon father and a schoolteacher mother, was one of the most valued customers in Las Vegas, a certified sucker with a drinking problem who was prone to blow $1 million or more per visit. The Golden Nugget, in downtown Las Vegas, kept a suite on permanent hold for Matthews and would dispatch the casino’s airplane whenever Mr. Rick got the itch to do a little gambling. He had a profitable fast-food chain called the Fryer back home in the deep-South Arkansas-Mississippi-Alabama region, where customers unafraid of the ravages of bad cholesterol could get all manner of oil-drenched comestibles, including battered Snickers bars. Whenever the betting bug bit, Rick would siphon off money from his own company, leaving it on the brink of bankruptcy. Fortified with greasy cash, Rick Matthews would lose every penny of his quarterly earnings during his forays to Sin City. But as long as the lard kept bubbling he could count on a steady stream of money to donate. It wasn’t that he didn’t want to win—he tried every spurious betting system and useless angle he could find. Matthews just didn’t know how to beat the house.

And then, after years of fruitless exploration, the lifelong action junkie finally discovered the key to the casino vaults. Rick Matthews figured out which football teams to bet on. The rumor going around Las Vegas was that Matthews had some sort of supercomputer tended to by a coterie of experts known as the Brains.

It wasn’t precisely a license to print money. But when you win three and lose two over and over, day after day, season after season, your fortune starts to stack skyward, like a pyramid in the desert. Unlike many sick gamblers, whose compulsions prohibit them from holding on to their winnings, Rick Matthews conquered his alcoholism, invested wisely, avoided leaks (bad decisions that inexorably erode a gambler’s bankroll), and continued to raise his bets while he was ahead. Which is a smart play when you’re on a twenty-three-year winning streak.

His name isn’t well known, but Rick’s prowess at prognosticating football games is famous. Even the hacks at my golf club in Los Angeles, who participate in a weekly pool, know that there are supposedly a few guys who can beat the point spreads consistently. My golf buddies have never met any of these wizards and couldn’t tell you what they look like. But the boys like to repeat the rumor that there’s a genius in Las Vegas who’s built his multimillion-dollar restaurant empire with capital earned from his sports betting exploits.

To the gambling cognoscenti, Rick Matthews is no rumor. He’s credited as the emperor of an operation that inspires fear in bookies and jealousy in aspiring professional punters. He’s the Michael Jordan of the wagering business, a man to whom the cliché living legend may be applied without embarrassment. One man moves the Vegas line. One man influences the way millions of people bet on sports. One man is a celebrity in a milieu otherwise devoid of stars.

Knowing I was eager to meet the legend for an interview I hoped to publish in a national magazine, a friend of a friend, another member of the secretive fraternity of professional gamblers, introduced me to Rick Matthews. Before I shook Rick’s hand and proposed that he allow me to include his tale in a book I was researching, my friend warned me about Rick Matthews. The guy is totally charming. A real sweetheart. But don’t let the southern gentleman deal fool you. When it comes to getting the best of it, the guy’s a stone-cold killer. You’ve heard of ice water in the veins? Rick Matthews has liquid nitrogen.

On the sixth tee, I watch Matthews hit a towering drive, an elegant parabola that rockets out to the right and slowly curls back to the left, coming to rest three hundred yards in the distance, bisecting the fairway. It’s the kind of golf shot I hit regularly—in my fantasies. I’m envious of Rick’s prowess, but not surprised. Before Big Daddy Matthews hit upon the secret to beating sports, he earned the bulk of his gambling winnings on the golf course. Rick, in fact, is one of the greatest golf hustlers of all time. Major champions like Lee Trevino and Fuzzy Zoeller have played with him, and they don’t look forward to wagering against him again anytime soon. Rick’s the rare bird who can shoot just about any score he needs to. When he was a bit younger, the talk around Sherwood Country Club was that Rick ought to take a crack at the Champions Tour when he turned fifty. But then everyone came to his senses and realized Big Daddy Matthews could earn a lot more money at golf staying at home playing against oil barons and telecom CEOs.

Now nearing sixty, Rick can still shoot in the seventies. And since there’s almost no amount of money he won’t play for, it’s impossible to make him nervous. When you’re dealing with a fellow who regularly wagers a million dollars on a football game, detecting a racing heartbeat during a friendly golf match is awfully difficult. So I’ve got no chance of winning today. Not a prayer.

Even against me, a nine-handicap with a piddling bankroll, the old hustler is loath to give away even the slightest edge. To make a fair match, I know I should be getting at least three shots a side. Rick insists on only giving me two—and that’s too generous! he complains.

We’re playing for twenty dollars.

I wonder: Does Big Daddy love to win? Or is he pathologically afraid of losing?

I’ve been eagerly anticipating my day on the greens with the legendary bettor. Since our introduction six months ago, we’ve spent several cordial and productive evenings together in Las Vegas. I’ve crafted excerpts from our chats into a story about sports betting, hoping to publish it in one of the slick periodicals during the heart of football season. It’s a good article, even if some of the choicest anecdotes were delivered off the record. Big Daddy has a habit of starting a fascinating story and then stopping in mid-sentence, smiling sheepishly, and declaring, Naw, I don’t think we should talk about that. But I can tell he likes me. Although I’m not officially part of his world—I don’t win and lose the average American’s yearly salary in one feverish night of action—I’m fluent with the vocabulary of people who look at life as a series of risk-versus-reward decisions. Most regular folks outside the surreal subculture of professional gambling see the high-rolling inhabitants of this parallel universe, where a dime means $1,000, as maladjusted freaks who could use a healthy dose of psychological counseling. The regular folks may be right. But there’s also something seductive and oddly respectable about men who are willing to back their convictions with a large portion of their net worth.

Ever since age five, when my great-grandma taught me how to play gin rummy, I’ve enjoyed card and board games: Scrabble, Stratego, Mastermind, Monopoly, hearts, poker—the excitement of an athletic contest and the intellectual challenge of problem solving have always appealed to me, a nerd with a competitive streak. But growing up with a healthy respect for money—my family never seemed to have quite enough of it—I viewed gambling with the cultivated skepticism of a striver inculcated in the twin virtues of Work and Study. Casino games fascinated me, since they were games after all. But losing hundreds of dollars at roulette and craps and slot machines, recreational pursuits that seemed as rigged as a carnival barker’s ring toss, was anathema to my stolid constitution. Part of me wanted to be a big winner. I wanted to take the risk. I wanted to overcome the odds with my wits and my guile. But I didn’t have the heart for it. Perhaps that’s why I was attracted to the rare fellows who did.

When I meet Rick Matthews in the summer of 1997, I’m thirty-two, moderately successful by the standards of normal American life but an inconsequential piker compared with the people I profile in the world of professional gambling. As a freelance writer, I contribute articles to a wide array of magazines, including several men’s publications that like to publish stories about wagering and Las Vegas, about big scores and big characters who heroically do what all of us working stiffs haven’t the heart for, men and women who play by a set of rules different from the ones we good citizens assiduously follow on our road to the pension and retirement home. These journalist assignments require monthly jaunts to Nevada, which remind me how much I like games, winning at games, and also how blasé and predictable my middle-class life is, how devoid of risk and its fraternal twin, reward. My biggest gamble involves appearing on a televised game show (and losing). My average blackjack bet is ten dollars. The poker tables I sit at produce wins and losses in the hundreds, not hundreds of thousands. I’m tickled when a casino pit boss offers me a comp dinner at the coffee shop (drinks not included). I pay the mortgage, I save for the future, I buy clothes and cars and concert tickets—and it all amounts to a rather ordinary variation on the theme of American triumph: You work hard, you endure the countless indignities of the unprivileged plebian, and then you go quietly.

The excitement in my life revolves around Vivian, my girlfriend of a year, a woman who is decidedly, willfully not average, not the usual middle-class gal obsessed with marriage and children. Vivian is what moralists would call a bad girl, a libertine who refuses to subscribe to the code of feminine conduct prescribed by church and state. She’s a pagan, a voracious reader of philosophy and science, and an omnisexual hedonist. To Vivian, Las Vegas is an adult playground, where every day is Mardi Gras and even the nicest people can be corrupted by temptations of the flesh. In Los Angeles, where we live together, Viv is an executive at a hotel company, a competent and presentable corporate achiever in a proper pantsuit. But when I’ve got a story assignment in the desert she likes to let down her hair (literally) and sate her carnal appetites. We gamble and flirt and go to underground adult sex clubs to play, and I feel at those fantastic, extravagant moments that I’m not just another anonymous young man hoping to find his way in the world. I’m doing something extraordinary.

When I began pursuing Big Daddy for my book project, I wasn’t conscious of wanting to work for him. If anything, I was simply keen to be let in on the secrets, to be given a glimpse of the recipe for his particular brand of special sauce. To see how one of the real rebels staked his claim to a grand slice of the American dream. Now, on Sherwood’s eighth green, I tell Rick Matthews, I respect your accomplishments. And I reckon a young man like me could learn an awful lot from someone as sharp as you.

Searching for ulterior motives, Big Daddy stares at me intently, as though I were a poker player he’s assessing for signs of weakness. Then he grins and says, Well, that might work.

A few holes later, riding up Sherwood’s closely manicured eleventh fairway, Rick Matthews nonchalantly asks me, Hey, pards, how’dya like to make a little money this football season?

Would my dog like a rare porterhouse for lunch? Like most American men, I bet a recreational pittance on the NFL games, and, like most American men, I win a bunch of games and I lose a bunch of games. I’m sharp enough to pick winners approximately half the time, but the juice, the bookies’ 11–10 vigorish, eats me up in the long run. I’m lucky if I break even.

I tell Rick, Sure, I’d like to hear how I could make some money betting on football. But could we talk about it later, after the round? I need to concentrate. I’m playing for twenty bucks after all.

Sure we can, Big Daddy agrees, chuckling softly.

We golf. He goes about his business with chilly precision and I don’t, so the outcome of our match is never in doubt. No matter how much I try to concentrate on tee shots and birdie putts, for most of the time I mull over whatever proposition might be awaiting me after the round.

When we’re back in the clubhouse, Rick spells out the plan: We’re going to be partners, which means I’ll bet his money as instructed. I’ll be part of his team of bettors, a squadron of associates who help him wager the enormous amounts of money he invests on every game. I’m not to play hunches. I’m not to divulge his picks to anyone. I’m not to reveal the source of my handicapping skill. And I’m supposed to wager all that I can.

Because of his reputation and the low limits the casinos impose upon him, Big Daddy Matthews can’t bet his own money in most places, and he certainly can’t bet enough to make it worth his while. He needs people like me to help him get down, to get his huge bankroll in play. In return for this valuable service, I’ll be entitled to 10 percent of the net profits. If we lose (which ain’t gonna happen), he absorbs the hit; if we win, I get paid a potentially substantial fee. I pay taxes on my share, he pays on his, and everyone gets rich. Plus, one day when we’re all through you can write a helluva book.

I’m going to contribute a small minority interest in the bankroll, which will mean I’m betting my own money as well, but the casinos may look upon this distinction as rhetorical hairsplitting. I ask Rick why he just doesn’t get one of the usual suspects, a salaried sportsbook runner, a human mule, to do the deed. He tells me that it would look better if a hotshot Hollywood type—or at least a guy who can play the part—flew into Vegas each weekend, looking like hundreds of other high-rolling suckers. Plus, Rick explains, I’m comfortable in the casino environment; I know the vernacular, and I can convincingly imitate the habits of a hopeless loser.

And most important, he says, he’s got a strong instinct that he can trust me.

Big Daddy Matthews has just invited me to join his team, the organization that those in the know call the Brain Trust.

I nod soberly and tell him I’ll think about it.

But I already know I’m in.

The next week I have supper with my friend Spanish Jack, one of the best seven-card-stud players in the world. Over margaritas at a downtown Los Angeles Mexican restaurant, I tell Spanish Jack about my opportunity to work with Big Daddy. Jack says that Rick Matthews has a reputation throughout the gambling world as a snake, a rat, a back-stabber, and every other lowdown epithet you could imagine. He’s the most successful gambler of all time. He’s probably won fifty to a hundred million. But you don’t want to be his partner. He just can’t stand not getting the best of every transaction. I’m sure he’s great to work for. He pays, and pays well. But you don’t want to have to trust him.

I’ve heard similar innuendos before from other professional gambler acquaintances, but I don’t want to believe them.

I’m still deliberating two weeks later when a men’s magazine assigns me to write a story about Las Vegas. It’s a good excuse to interview Eric Jox Brijox, the man who creates the Las Vegas line, the guy whose job it is to make it difficult for people like Big Daddy to make a living. We’re sitting in Jox’s office, a brightly lit workspace decorated with sports memorabilia, in a corporate park not far from the Vegas airport.

Jox, a former statistician with a major aerospace concern, has a pasty complexion and thick eyeglasses befitting a fellow who spends most of his waking hours in front of a computer monitor analyzing batting averages and rebounds per game. The Las Vegas casinos—and dozens of others around the world—pay Jox a monthly fee to help them set their opening point-spread numbers, which Rick Matthews and friends subsequently comb for weaknesses to exploit. Jox doesn’t like Big Daddy. He says Matthews is a compulsive liar and a scoundrel in general, a guy who refuses to follow the casinos’ rules on betting limits. I can see the distaste on Jox’s pale, boyish face when he talks about his chief nemesis.

Without revealing that I’m pondering joining the Brains, I tell Jox that I’ll probably take a shot at beating football this season. I tell him I’ve come into a substantial amount of money and that my neighbor, a computer whiz, has a program that can pick something like 60 percent winners (52.4 percent is break-even). Does Jox have any thoughts?

He tells me he’s skeptical and says that if I ended up the season losing only a little he would consider it a huge success.

I glance over Jox’s shoulder at the framed photo of Secretariat winning the Triple Crown at Belmont. I say I’m confident of my system. I’m planning on betting a lot. Might as well put my money where my mouth is, right? Any reason I shouldn’t?

Because you’re probably going to lose! Jox predicts, chortling. I make a pretty good line, you know.

I think about how Jox sets that line, how hundreds and thousands of sports statistics are fed into a computer on an hourly basis, stats that are analyzed by a program created and fine-tuned by Jox and his crew of geniuses. For the average sports gambler, Jox’s line is tough. The best, I reply reverentially. But I’m thinking, It’s not infallible.

Outside Jox’s window, another plane lands at McCarran Airport, depositing hundreds of fresh suckers in the desert. Their cumulative wisdom about gambling wouldn’t come close to equaling what Eric Brijox knows about risk and reward. Yet even he, I realize, can’t stop syndicates like the Brain Trust from beating the Las Vegas sportsbooks. There’s a reason they’re called the Brains: They simply seem to know more than anyone else does. To most casual players, the point spreads are as solid as the commemorative baseball bat, signed by Reggie Jackson, hanging on the wall behind Brijox’s head. To Rick Matthews, they’re as fragile as a crystal champagne flute.

Here’s my plan, I explain. Either I’m as good as I think, or I’m going to go down in flames. So I’m going to bet as much as I can afford. We talk about the Kelly Criterion, a formula for determining the optimal percentage of one’s bankroll to wager on each game, and other mathematical arcana beloved of serious gamblers and math wonks—but really I just want to put the proposition in front of Jox. I know if I end up betting big sums, some sportsbook manager is going to call Jox the Linemaker and ask, Who the hell is this precocious kid? If Jox tells them I’m just some punk writer, things might look suspicious; if he says I’m a gambling author with the dumb luck to have a big bankroll and a funny idea in his head that he can beat football—well, then they’ll probably be happy to take my action.

Jox asks how much I want to bet. I tell him I don’t know—$20,000 to start, $30,000, maybe even $40,000, depending on how good my system is. Jox laughs. That’s going to be tough to bet that much. There’s only one guy who knows how to get that much down. You want that kind of action, you better get in tight with a guy like Rick Matthews.

I swallow hard and try to keep a straight face.

Season One

Autumn 1997–Spring 1998

Two

High Roller

When my girlfriend Vivian and I arrive at McCarran International Airport at 8:30 on a Friday evening in September 1997, I ring Big Daddy’s cell phone, as instructed. He tells me he’s glad I’ve arrived and asks me to call him back after I’ve checked into Caesars Palace, one of the first super-luxe themed casinos on the Las Vegas Strip and one of the few older properties to keep up with the increasingly hip and modern Vegas. The excesses of the Roman Empire are celebrated at this world-famous resort, where every man, no matter how plain his title back home, can be an emperor. Lurid blue lights illuminate the front of the hotel, whose building-sized marquee and ornamental fountains have appeared in dozens of movies and television shows as visual shorthand for Vegas grandiosity.

It’s the second week of the college football season. Since our fateful golf date, Big Daddy and I have had one terse conversation during which I agreed to his generous terms. I was fully briefed on my responsibilities. Then, using my real name over a series of increasingly credible phone calls, sweet-talked the casino management into believing I’m a whale, a big-betting sucker worthy of the finest amenities—despite the fact that the biggest wager I previously placed at a Las Vegas sportsbook was $220 to win $200 on a football game.

Now the real fun begins.

Every employee at Caesars wears a uniform that is supposed to suggest ancient Rome, however tenuously. Even the parking valets, who take our rental car and summon a bellman for our luggage, are dressed up as some sort of characters, though I’m not sure as what exactly. (Well-kept slaves?) So many incandescent lights glow near the front entrance, a horseshoe of glass doors on top of a wedding cake of stairs, that the air is measurably warmer near the doors than on the expansive stone driveway. At the front desk, a great slab of white marble, the nice lady checking my reservation tells me that thanks to my management-approved status, I could have availed myself of the Invited Guest Lounge, where patrons hand over their credit cards and driver’s licenses while attendants bearing canapés speak in hushed tones and fetch cool drinks.

I call Rick Matthews from our room—a superior model, with a Jacuzzi, a circular bed, and a mirror on the ceiling. It’s not the Rain Man suite, but the abundance of gold-plated faucets and marble flooring suggests that the casino wants the room’s occupants to feel like patricians of Caesar’s empire or, at the very least, facsimiles of Tom Cruise. The bathroom amenities are arranged on platforms held up by miniature Doric columns, and the pay-movie channels, I discover, don’t require payment. They’re all activated.

Viv and I have been together for more than a year. We’ve been to Vegas a dozen times before. We’ve never stayed in a place like this.

Big Daddy tells me to meet him out front in thirty minutes. I’ll be driving a black four-door Mercedes, he says in his lazy drawl.

Half an hour later, after escorting Viv to her bubble bath, I’m waiting alone under the porte cochere, watching the limousines and taxis disgorging passengers. Rick pulls up and waves when he spots me in my white Shadow Creek golf cap. Only the loftiest of high rollers get invited to play at this ultra-exclusive North Las Vegas private course, where people like Michael Jordan and Phil Mickelson keep lockers. Journalist credentials allowed me to sneak through the filter that’s supposed to keep out people whose net worth is below $10 million. (And I bought a hat to commemorate the occasion.) Now, I’m thinking, the Shadow Creek memento will broadcast to the world—particularly the management at Caesars Palace—that I’m a terribly desirable casino customer. After all, I’ve played at Shadow Creek.

On the passenger seat of Rick’s car is a legal document that acknowledges my participation in the Brain Trust betting syndicate and a list of the games I’m supposed to play. It’s a plain white sheet of paper, with black type, frank and unadorned. Big Daddy says, Howya doin’, pards? They treatin’ you all right? as I climb inside.

Before I can answer, he says, Let’s make a visit and go get you some money.

We drive downtown to the Union Plaza. As we pass successive casinos along the Strip—Mirage, Treasure Island, Frontier, Riviera—their lights winking like flirtatious girls, Rick eviscerates the city of Las Vegas. I’m so disappointed by what’s happened to this town, he admits, shaking his head. They all smile at the suckers, pretending that everyone has got a decent shot at winning. But, Mike, you’re gonna find out: If you show any speed whatsoever they’ll bar you in a second. Bunch of frauds, these people are, he mutters.

I look over the list of the Brain Trust’s picks. A few are popular televised national matchups, such as Wisconsin vs. Illinois. But most are obscure regional games, which, I fear, will set off alarm bells with the bookies. Akron vs. Toledo, Western Carolina vs. Ball State, Ivy League contests. Even I know only wiseguys play these games.

Rick parks outside the Plaza and leaves me in the car. I read and sign the legal document, which basically says I’m holding a lot of the Brain Trust’s money. Then I rewrite the shopping list of football games in my own messy scrawl.

He returns a few minutes later with a leather bag containing $400,000 in bundled hundred-dollar bills. I hold the satchel between my legs. It feels as though there’s a bowling ball inside. I’d have to write one major story a month for close to eight years to accumulate what’s in the bag.

Back at the Palace’s front entrance, Rick and I transfer the money into two shoe bags—golf shoe bags. FootJoys. Go win some bets! Big Daddy says.

Yes, sir, I reply and bolt into the casino.

Realizing I’ve forgotten my Shadow Creek hat, I dash back to the curb. He’s still there, watching me.

I go directly to the sportsbook, a cavernous room with a forty-foot-high ceiling and wide-screen television monitors blanketing the space like animated wallpaper. The back wall behind the service counter, where patrons make bets, and which looks like the hotel’s front desk, is entirely dedicated to a digital toteboard listing the current betting odds on hundreds of contests. The backdrop of ESPN’s SportsCenter set is modeled on such a toteboard. Dina, the night supervisor, greets me. Gino Miceli, the vice president of sports and horse racing (and Dina’s boss), a former Brooklyn pizzeria owner turned casino executive, told her I’d be coming and to take good care of me. I phoned Gino earlier in the week and he didn’t seem too interested in my fanciful story of hitting it big in Hollywood and wanting to scratch my action itch. He just wanted to know when I was coming and how he and his staff could make my visit to Caesars special. Let me win! I barked.

I plunk the shoe bags on the counter. I’d like to open a betting account, I tell Dina as she eyes the mountain of money. And oh, by the way, could you scare up a couple of buffet tickets?

A portly woman with round cheeks, Dina titters obsequiously at my joke. Her entire face jiggles when she laughs. I’d previously seen a couple of small-time bookies, outlaws who operated out of basement poker rooms and sports bars. Dina’s not what I pictured a professional casino bookmaker would look like.

The sportsbook air is filled with the low hum of televised highlight shows and the pungent aroma of cigarettes and perspiration, the by-product of excessive adrenaline and anxiety. Dozens of sports fans congregate beneath the broadcast screens and toteboard, silently wishing and praying and willing their team to win tomorrow’s game so that they too can win. There’s a sense of desperation already, and none of the contests have even started.

For the next hour we fill out paperwork and count the money. Though two clerks work on the stacks of bills, counting them into $10,000 packets, it takes thirty minutes, and I quickly exhaust my supply of small talk, leaving me and Dina in uncomfortable silence. I’m given tickets to a VIP table, in the middle of all the screens, a prime location to root and holler and play out private dramas in public. While the employees count and package, I make some noise about being a big poker player down at the Horseshoe. But no one seems to care where the money came from, only that it’s probably going to end up staying with Caesars Palace.

Dina asks me if I want to bet tonight. I say yes, and as a courtesy she gives me an updated list of the current lines so I don’t have to wait for my games to appear on the toteboard, like stocks flickering past on a ticker. To my dismay, none of the games are posted at the point-spread numbers Big Daddy has ordered. It’s only a half point or so that they’re off, but the rule is clear: Wrong number, no bet. I tell