6 Fascinating Facts Learned From An Interview With A Modern Day Bookie

A friend and I put down $100 bucks a piece on the Tampa Bay Buccaneers over the Oakland Raiders in XXXVIII. Obviously, if you know sports, we won. It took over two weeks to collect our money.

The bookie was a big time somebody in a town full of nobodies. The prodigal’s son had returned because he couldn’t swing a bat and hit a ball with enough consistency to move up a level in minor league ball. He decided to become a bookie because working in an office was probably too demeaning. I’m not sure if he’s still in the game, twelve years later, but I don’t imagine he lasted too long if he couldn’t even pay up such a small sum. I still see his name around town, hovering over crossing bats and balls on posters and lawn signs, in another attempt to take money from people.

Bookies and sports betting are much different now. Sure, they probably still hunt down people who don’t pay up and still live a shady existence, but these days almost anyone could take bets and money from strangers. All they really need is a website and face that says “pay up or things will get uncomfortable.”

This fascinating piece on Playboy.com details the life of one such fella, Roland, and how bookies today are different than the period pieces seen on TV. He’s a little less Tony Gazzo from Rocky but a little more Bobby Baccalieri from The Sopranos.

Here are just some of the more fascinating parts of the interview.

If You Don’t Pay, Your Buddy Is Screwed

“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.

Gambling Always Makes Things Worse

“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.”

Sometimes, Just Sometimes, A Bookie Will Do The Honorable Thing

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.”

It’s All Computers These Days

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.”

The Charming Bookies Of The Old Days Are Long Gone

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.”

Even Bookies Need Real Jobs

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.”

Check out the complete interview here.

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Chris Illuminati is a 5-time published author and recovering a**hole who writes about running, parenting, and professional wrestling.