Twitter Facebook Instagram Google+ Tumblr YouTube E-Mail WhatsApp Sign In Check Close snapchat
Search
Exit Clear

10 Hours A Week, $70,000 A Year: The Life And Times Of A Modern-Day Bookie

10 Hours A Week, $70,000 A Year: The Life And Times Of A Modern-Day Bookie: © kevin walsh / Alamy

© kevin walsh / Alamy

My Bookie’s name is Roland.*

Obviously, that’s not true, but that’s what we’re going to call him. I’ve never been dumb enough to ask him for a last name, but since I’m a gambling man, I’ll wager it ends in a vowel.

Every few weeks I meet with Roland in a random North Hollywood parking lot to square up. And by square up, I mean pay out. I walk up to his car window, pleasantries and money are exchanged, and we both go our separate ways. One time he drove up in a white Escalade with his son strapped into a car-seat, looking blissfully unaware that my gambling losses had probably paid for his OshKosh B'gosh overalls. Otherwise the meeting is always the same: Roland sorts through my money with the speed and accuracy of a bank teller, so it only lasts about thirty painful seconds. His five o’clock shadow is perpetual: maybe he shaves Monday through Friday when he’s busy working his day job in insurance. When I see him on the weekends, he’s too busy raking it in to worry about a little stubble.

Win or lose, Roland isn’t unfriendly. But he isn’t exactly handing out smiles. He’s learned to walk the fine line between friend and enforcer. I’m not afraid to shake Roland’s hand, but I get the feeling he’s not afraid to break mine. As for why he agreed to be interviewed, I don’t really know. I just asked him, and he said sure. We had coffee a few times, and he asked not to be identified. Other than that, there were no conditions.

Like everyone who deals in vice, Roland sells a cheap thrill. But unlike bartenders, drug dealers and sex workers, he has no physical product. You can’t smoke a point spread or bury your face in between an over-under. A gambler gets high off the action. And unfortunately for bookies, they can’t collect until after the action is over. This means every client is a potential liability, especially when times are tough.

“When the economy tanked, guys started betting crazy,” Roland said. “They’d go from betting a few hundred to losing $2,000 a week, throwing good money after bad trying to make ends meet.”

Given these circumstances, Roland has to be cordial enough to avoid alienating his customers yet threatening enough to keep us in line.

“Remember, if you decide to skip town, I’m going after Sam for the money,” Roland told me the first time we spoke.  

Sam (not his real name) was a fellow degenerate who introduced me to Roland. His reward for bringing me in as a new client was to be held liable for any future losses I failed to pay. It was harsh, but I couldn’t fault Roland’s logic: no one in their right mind wants to vouch for a deadbeat gambler—especially not another deadbeat gambler.


The concept of placing bets with an actual human may seem antiquated, particularly to those born in the 1990s. But unscrupulous business practices and government crackdowns such as the 2011 “Black Friday” poker raids have left many gamblers wary of wagering online. This helps cash-only bookies like Roland. His bets are paid face-to-face rather than through credit cards or bank accounts, which means they’re far less traceable.

There’s also the matter of customer service. During Super Bowl XLVI in 2012, I wagered that there would be no score in the first five minutes. Thanks to a strange play involving a penalty-induced safety and an even stranger method of timekeeping by the NFL, I was robbed of my money, or at least I would have been if not for Roland’s sense of honor.

“As a bookie, I have to go by the official time,” Roland said. “But as a man, that’s bullshit, and I’m going to give it to you.”

This personal touch is what makes a bookie like Roland superior to a computer. (Unless you don’t have the money to pay, in which case that personal touch might cost you the use of your legs.) But don’t mistake old-school for old-fashioned. The same online technology that once threatened to crush local bookies has been co-opted, allowing them to not only survive, but thrive.

For a small weekly fee, Roland uses an online service based in the Caribbean. It provides his customers with a fully functional gambling website covering everything from horse racing to English Premier League soccer. But unlike a normal online sportsbook, no money is transferred, which means circumventing the government isn’t a concern. The site is just a middleman that tracks my bets, and keeps a running total of how much Roland owes me (or more likely, how much I owe Roland).

“It’s a software system, nothing more,” said Roland. “I don’t even move the lines. It’s all automated.”

While local bookies were able to adapt and survive after the advent of online sportsbooks, they still face the very real threat of legalized sports gambling, which would cripple Roland’s business.

“It would be devastating,” Roland said. “There’s a Tilted Kilt not far from here that allows off-track betting. If it was ever that easy to bet on football, there’d be no way to compete.”

Luckily for Roland, the federal nanny state has no intention of allowing legal sports gambling to spread. Last month, a U.S. District Court rejected New Jersey’s efforts to allow sports wagering at racetracks. This was a victory not only for the NFL, which made vague arguments about the “irreparable harm” posed by legalized gambling, but also for small-time bookies. Thanks to the ruling, Roland and his colleagues will remain in business, and an estimated $380-billion worth of illegal sports bets will go untaxed every year.


Roland’s current system is a far cry from his humble beginnings. While attending college in Los Angeles during the late 1990s, he started taking action on football from a few friends using odds he found printed in the newspaper. Before long, news of an on-campus bookie spread, and his business ballooned to 80 clients. One fall evening, after returning from a night class, Roland turned on his phone to find 65 messages from angry gamblers desperate to get in on the Monday night game. At this point he started skipping school to focus on business.

Soon, he implemented client account numbers and brought in two assistants: the first to help field calls, the second to help with collections.

“I hired a dirtbag to go after deadbeats,” he said. “I felt bad about it.”

But his guilt was quickly assuaged by cold hard cash. As the years went by, Roland’s book continued to grow. Between 1999 and 2000, he pulled in more than $250,000 taking bets strictly on college and NFL football.

This sort of money didn’t go unnoticed by established bookies in the area. But unlike in the movies, where challenging an existing racket will get you killed, Roland’s newfound success presented him with a business opportunity; a competitor offered to buy a 50 percent stake in his book.

“He’s an old-school Italian guy with 40 years in the business,” Roland said. “He’d never talk to you.” But despite his partner’s ethnicity and “old-school” persona, Roland claims the mafia gambling racket we see in film and television is a thing of the past, at least in Los Angeles.

“Chicago might still be mob,” he said with some skepticism. “And I’m sure there’s some Asian gangs down in Chinatown. But we’ve never had to pay up to anybody.”

The partnership allowed Roland to scale back his operation to a more manageable level, which means he can be more discriminating when taking on clients. He’s down to about 35 active, more trustworthy gamblers—including doctors, lawyers, entertainment executives, and of course, a few police officers.

“I play poker with a lot of cops, so I’m never worried about my game getting robbed.”

But despite the smaller scale, Roland still makes between $50,000 and $70,000 a year in secondary income after splitting with his partner. This isn’t surprising, considering only three of his clients make a profit on a consistent basis.

“There’s a banker who makes a few key bets per week,” Roland said. “He makes about $500 to $1,000 a week.

The rest of us aren’t so lucky.

“I see all of the totals, and over the long term, no one else makes money.”

Even during his worst year, Roland still ended up making $23,000. That might not seem like much, until you consider he only works as a bookie about 10 hours a week. But during his more lucrative years, he’s made $135 an hour.

“It’s mostly drive time,” he said. “One guy I know used to run a book out of his sandwich shop, so all his clients had to come to him,” he said.

“The sandwiches were pretty good.”


While a $135-an-hour side job that doesn’t involve sex with strangers might seem like a dream come true, there’s always the issue of getting caught. His own partner has been nabbed multiple times, but always ended up getting off with probation.

“I should worry more,” he said. “But I don’t. The guys who are getting busted are usually breaking legs. That’s just asking to get noticed.”

But like anyone who knows the story of Al Capone, Roland still has a healthy fear of the Internal Revenue Service. “I report all my profits as gambling winnings,” he said. “I pay my taxes. The only thing they can charge me with is bookmaking, which is a slap on the wrist.”

While there was a time when deadbeat customers could expect more than a slap on the wrist from one of Roland’s collection agents, his current system is far less brutal. “I never felt good about having guys roughed up, especially after I had kids,” he said, seeming sincere. “Now I cap losses and allow for a slow payback if necessary. Once a guy gets paid back to a certain point, I tell him it’s over, and that I better never see him again.”

And if he does see him again? “I ran into one guy, but I just pretended not to notice.”

While the new system is good news for customers on a losing streak, it means Roland is taken advantage of from time to time.

“I had one guy, a poker player, stiff me for $7,000,” he said. “Last I heard he fled the country.”


Some of the story’s details and the author’s name have been changed to protect the guilty.

Playboy Social

Never miss an issue. Subscribe and save today!

Loading...