Walking the line

Corner bookie Floyd Fielding makes his living the old-fashioned way: One loser at a time

Updated: August 13, 2012, 4:34 PM ET
By Tim Struby | ESPN The Magazine

Floyd FieldingJessica Dimmock/VIISometimes a cigarillo is just a cigarillo. But not when that cigarillo is being smoked by a bookie to mask his identity. For Fielding, a smoke screen is all that stands between him, identification and prosecution.

This story appears in the March 5, 2012 "Analytics Issue" of ESPN The Magazine. Subscribe today!

IN THE NEON glow of Manhattan's Times Square, a black sedan glides through the streets. At the wheel sits Floyd Fielding*, armed with his essentials: cigarillo, Uni-ball pen clipped to his T-shirt, four cellphones at the ready. On this Tuesday night in November, he'll make eight stops from Battery Park to the Upper West Side. He does not speed or text while moving. He drives cautiously -- not only because of the pre-holiday crowds but because Fielding, by the nature of his business, is a cautious man.

After parking in front of an Irish pub, he pulls an 8-by-6 index card from his jacket and scans several rows of hand-scrawled names. He grabs an envelope, a standard No. 10 white-wove envelope that he buys in boxes of 500 from Staples. He double-checks its contents -- six hundred-dollar bills -- and crosses a name off the card. He gives a listen to the Duke-Michigan State game on the radio. He doesn't care that a Duke victory will make Coach K the winningest coach in men's college basketball history. He's concerned only with the score: Midway through the second half, the Blue Devils are up 20. He's got a "couple of bucks" riding on the outcome -- in Fielding-speak, somewhere from $1,000 to $5,000.

"At least I'll win this game," he says, confident Duke will cover the seven-point spread. For the past 14 years, Fielding has made a living passing envelopes -- in the back rooms of bars, in crowded restaurants, on city sidewalks and behind tinted car windows. He's not a violent thug or a member of organized crime. He's a 41-year-old independent one-man bookmaker. And business is booming.

Fielding spends precisely 50 seconds inside the pub. Over the next hour and a half, he'll stop at three midtown pubs, a West Side bar, a posh Upper East Side prep school (to collect from a custodian), a Murray Hill walk-up and a waterfront penthouse. He operates with the efficiency of a deliveryman on a Boar's Head route. The only difference is the guy dropping off Virginia ham isn't picking up $25,000.

Around midnight, Fielding crosses the last name off his index card and turns his attention back to the radio. He hears celebrating, talk of Coach K's record-setting 903rd win. But his smile turns to a sneer when he hears the 74-69 final score. Fielding scoffs, then puts the car in drive. "Didn't even cover the points," he says.

SUNDAY MORNING, and little stirs in Fielding's neighborhood. It's a tree-lined block an hour outside of New York City, with aluminum siding and aboveground pools. Its residents, like Fielding, are second- and third-generation immigrants -- Italian, Irish, German, Polish.

[+] EnlargeFloyd Fielding
Jessica Dimmock/VIIOver the years, Fielding has sought a higher class of clients -- bankers and bar owners, the kind of people a bookie does not have to slug in the face.

Sitting at his kitchen table, Fielding noshes on a buttered bagel. Nearby, his 8-year-old son scribbles a crayon masterpiece while Ann, his wife of 10 years, a sort of Peggy Bundy with a makeover, chides Floyd for his religious shortcomings. Theirs is a well-worn comedy act, a domestic "Who's on First?" routine. "She's always trying to get me to go to church," says Fielding. "I tell her I pray every Sunday. At the altar of the NFL."

Ann rolls her eyes. She's heard it before, been aware of his profession since almost the first night they met at a downtown New York bar. She was waitressing. He was taking bets. As a regular and a friend of the owner, Floyd seemed harmless enough when he asked for her number. Still, she passed when he called. So he called again. And again. Twelve times a day for a week, somewhere between stalking and endearing. Finally she relented. Two weeks later, as they sat in his Camry, he revealed he was a bookie.

At first, it was a mystery. Ann didn't understand that losing $10K on a Monday wasn't the end of the world. Or that thanks to the 10 percent vigorish, bettors had to win 52.4 percent of the time with Floyd just to break even. Or that as long as he remained a cautious man, he'd do just fine for himself. Five months after their first date, they married. Now she's the one calling him while he's spending long hours on the road. Making sure he's okay. Seeing whether he'll be getting home at a reasonable hour. Simply hearing his voice. "Sometimes I wish I could lose all the world's balls," she says as she makes her man some coffee. "No more playing."

At 11:30, Fielding heads upstairs to his office. The decor of the 12-by-8 room might be described as minimalist-superstitious: beige rug, TV, two desktop computers, landline, printer, a leather chair, two money tree plants (allusion intended), half a dozen bulbs of garlic (to ward off evil), green walls ("money-colored," as Floyd calls them) and a paper shredder. From here, Fielding oversees his business, much of which has remained unchanged for 14 years. He carries 62 clients. All but one are male. All live or work within driving distance. Each has a settle-up number from $500 to $5,000. As for Floyd, he makes a good living. "How much do I make?" stammers Fielding, unsure of how to walk the line between truth and self-preservation. He considers his $750 weekly overhead -- the gas, phones, online costs, the taxes he pays as an "independent contractor."

"Six figures. But I can't retire anytime soon."

According to a report by the National Gambling Impact Study Commission, legal gaming revenue increased 1,600 percent from 1976 to 1997. A recent CNBC investigation reported that roughly $300 billion is wagered illegally in the United States. Meanwhile, a 2003 study on illegal bookmaking by an economics professor at the University of North Carolina found that only 10 percent of such money is wagered through the Internet. The rest is bet through guys like Fielding. "How many bookies are out there?" says RJ Bell of, a gambling information website. "There are a lot more than five years ago."

Fielding accepts bets on a wide range of sports, from the obvious (football, baseball, basketball, hockey, tennis, NASCAR, horse racing, boxing, MMA, golf) to the less so (volleyball, snooker, Australian Rules football, rugby, cricket). The NFL attracts the most action by far and, on this day, he estimates that 98 percent of his clients will wager, from $50 to $5,000 per bet. Wearing a headset, he mans his desk with the efficiency of an air traffic controller: answering calls, replying to texts, jotting down wagers and balances in his notebooks, studying his favorite consensus websites, answering more calls, extending $2,000 of credit to a client, tweaking his lines. His opening spread follows Las Vegas, but once the calls come in, it's all Fielding and his intuition.

If you're gonna affect my job, I'm gonna affect yours.

-- Floyd Fielding

Technology, specifically the emergence of online sportsbooks, was once expected to mark the end for "corner bookies" like Fielding. The first site, Intertops, was founded in 1996 on the island of Antigua. During the next 15 years others popped up like dandelions, from tiny operations to billion-dollar businesses like Bodog (now Bovada) and BetOnline. Still, many gamblers have never taken to the virtual experience: money required up front; difficulty setting up accounts; winnings held for 10 days; sites shutting down unexpectedly. Perhaps the biggest issue? Personal care. "A bookie is a service industry, no different from a lawyer or an accountant," says Shaun, a bartender and longtime Fielding client. "Floyd's always reliable, available and pays on time. Not to mention he's a damn nice guy. If someone's gonna take your money, it might as well be someone you know and like."

As the 1 o'clock kickoffs approach, the beeping, pinging and ringing of incoming bets grow more incessant. "Instead of making bookies obsolete," Bell says, "technology has helped them flourish." Cellphones mean no more eight-hour days at a desk or hovering over pay phones. Texting eliminates needless banter. But for an independent bookie like Fielding, flourishing doesn't mean freedom.

He has no one to answer his phones. He doesn't trust anyone to handle his pickups. And he knows he must take action every day or else clients will find another bookie, no matter how friendly he is. "I've got two genuine days off a year," says Fielding. "The day before and the day after baseball's All-Star Game."

At precisely 1 p.m., the phones stop ringing. A respite before the late-game action begins. He goes downstairs. Grabs another diet Pepsi. Descends into his basement. Past the cat litter boxes, he enters a room. There, on stands and in cases, is his guitar collection -- Fender Stratocaster, Gibson Les Paul, Gretsch White Falcon. They're the same models used by his heroes -- The Edge, Jimmy Page, Brian Setzer. Fielding picks up the Strat. Strums the strings. He can't play but a few chords. He talks of his first-ever concert: U2, 1985. The Unforgettable Fire tour. He and his older brother in the nosebleeds at Madison Square Garden. He recites, in order, the entire 18-song set list.

Straight out of college, Fielding landed a job with a major label in the A&R department. His dream? To find the next Bono. But in lieu of camaraderie, he found interoffice fighting, backstabbing. After two and a half years, he quit.

Since college, he had been gambling with a bookie. "It started with football," he says. "After a year I was onto basketball, baseball, you name it." After a bad run, he looked to switch bookies; through a friend, he met an Eastern European immigrant who'd run his own book for four decades. In Fielding, the old man saw a kindred spirit. So when Fielding left his job, the old bookie offered him seed money to start his own operation. Disillusioned, unemployed, fully aware of a bookie's potential bottom line, Fielding couldn't pass it up. "It's not like I ever wanted to be a bookie," he says. "But sometimes life isn't what you expect."

A NIGHTMARE. That's how he describes his first five months as a bookie. In his years of gambling, he'd seen runs of bad luck before. But not this bad. In 20 weeks, he was down $50,000. These days that would sting, but he wouldn't panic. He wouldn't have the sleepless nights he did then. But the old guy kept assuring him everything would be okay. Kept loaning him money, interest-free, to stay afloat. "I was already nervous about starting out on my own," he says. "Then I find myself in a world of trouble." He didn't fold, kept taking action from his office in his parents' basement. By Week 8 of the NFL season, he'd made it all back.

Still, those early years were tedious. "Starting out, you have to deal with some scum," says Fielding. "And in this business, if you haven't hit a few people ... " He tells of one unsavory client who'd been avoiding him. Spying the guy at a Queens bar one evening, Fielding called up some muscle and waited. When his client went to the bathroom, Fielding steered him out the back door instead. "I was doing all the hitting," he says. "My big guy was there just in case my client decided to hit back."

Fielding lights another cigarillo. A wiry man, slight of build, he hardly reeks of danger. Yet he doesn't regret the use of violence. It was necessary, he says. It set a precedent. Eventually, though, bookies must stop hitting people. So over the years, Fielding sought a higher class of clients -- bankers and bar owners, the kind of people a bookie does not have to slug in the face. He doesn't do credit checks, but he vets all prospective bettors. Calls them up. Sits down with them. Asks a few simple questions: What do you do for a living? What neighborhood do you live in? How much are you comfortable wagering? "I'd prefer to take $100 a week forever," he says, "than have a guy lose 10 dimes and not be able to pay."

If a client tries to avoid payment, Fielding might even offer an interest-free payment plan or, for heavy hitters, a rebate, cutting a debt from $50K to $30K. He's also developed new varieties of intimidation tactics. "These days, it's all about psychology," he says. He'll call a client at home or text him his home address -- even though the client never provided that information. He'll threaten to print out a client's gambling history and send it to the man's wife. Or with a goon by his side, he'll drop by a debtor's workplace. "If you're gonna affect my job, I'm gonna affect yours. And believe me, you go to someone's office with a big guy, it's very effective."

Sometimes I wish I could lose all the world's balls. No more playing.

-- Ann Fielding

It also means less chance of someone ratting on him -- and makes the odds of getting arrested surprisingly low. Prosecuting financial crimes requires time, money and manpower. "The only way a stand-alone bookie like Fielding gets caught is in a Spitzer situation," says a former Manhattan assistant district attorney. "Someone files a Suspicious Activity Report on someone like a politician or an athlete. Investigators then look into phone records, bank records, and that leads to the bookie. They bust him only so he'll talk about the original target of the investigation."

Fielding remains perpetually cautious. Every month he has his landline checked for wiretaps. Other than a rare summer barbecue, he doesn't fraternize with his neighbors. His business cellphones are disposable, untraceable. He keeps a list of his aliases taped to his computer monitor. He doesn't buy Ann furs. Shops at Target, never Saks. And while $100,000 worth of new sports cars are parked in the driveway next door, Fielding rolls in an '04 Chevy. At a Sunday wedding last year, a nephew asked Fielding why he was constantly on the phone and taking notes. "Because Uncle Floyd's a travel agent," he answered.

His real fears are financial: the IRS getting nosy. A big client getting hot -- which, in the past, has cost Fielding upward of $200,000. (Fielding says he always keeps a six-figure stash of ready cash to handle unexpected losses.) Organized crime stumbling across his operation, shaking him down for a share of his profits. "Sharp" players or syndicates, who use sophisticated algorithms and inside information to gain an edge over unsuspecting bookies. Fielding knows this situation all too well. Two years ago, based on a referral, he took on a new high roller. Despite a $3K per-game credit level, the client didn't place a bet for two weeks. Then he bet once but lost. "The next week he gambled more and was up about $10,000, but I wasn't worried," Fielding says. He got worried in a hurry, however, when the new client began placing -- and winning -- obscure wagers. Hitting a never-before-heard-of horse for $50,000. Betting that the Buccaneers score under 7.5 points in a game. "Who does that?" says Fielding. Someone who knows more than the bookie, that's who. Fielding shut down the client's account. "It was a lesson learned," he says. "An expensive lesson."

ANOTHER TUESDAY NIGHT. A cold rain falls. Fielding enters a nearly empty Upper East Side bar. He sits beside Seamus, a Belfast bartender on his night off, and Ted, the manager of a nearby wine shop. Both are clients.

"What's up, fellas?" says Fielding.

They greet each other with handshakes and pats on the back. They tease Seamus about his beloved Jets not covering against the Bills. They talk of Floyd's treating them to steak dinners at Delmonico's, taking them to see U2.

The bartender, Shaun, approaches and hands Fielding an envelope of his own. "Whatcha having tonight, Floyd?"

"Club soda," he says, placing $20 on the bar. "And back these two guys up."

A few minutes pass, the banter fades and the men silently watch the first half of the Marquette game on the overhead TV. Fielding is unusually quiet. Tired. A byproduct of the grind, he says. The everyday grind of traffic, parking, accounting, his kid, his wife, working week in and week out, every holiday, every birthday. But it's more than that. The duplicitous life is also tiring. The secrecy, the lies, the loneliness. Self-preservation means keeping almost everyone at arm's length. Sometimes he imagines being in the mob, having a crew. It'd be more dangerous and he'd make far less money, but at least he'd have confidants.

He talks, during times like these, of going legit. Saving enough money to open a bar. He'd take his son to school every morning, dabble in day-trading, cover a bartending shift or two. "It'd be nice to have a normal life."

But after 14 years in the shadows, it ain't easy stepping into the light. Where else could he earn as much? What other job could provide the thrill he still gets from being handed an envelope with a fat stack of hundreds? "I know part of him wants to get out of the bookie business," says Ritchie, his best friend of 17 years. "But after a point, you're too far into it. You really can't do anything else."

The first half of the game winds down. Marquette brings the ball down for a final shot. It clangs off the front of the rim. Fielding nods. Makes a note in his book. Minutes later the phone rings.

"Hey, baby," he says to his wife.

"Yeah, I'm working."

"Don't know when I'll be done."

"Yeah, we're still on for tomorrow ... Promise."

He hangs up. Sets the phone on the bar. "I just won five grand," he says. "And tomorrow I'm taking my family out to Applebee's."

*Names and certain identifying details have been changed. Tim Struby is a contributing writer for ESPN The Magazine. Follow The Mag on Twitter, @ESPNmag, and like us on Facebook.