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How to Get Into Sketchy Sports Betting

Most sports betting is still underground, but the internet has made it more convenient. Paying off your illegal gambling debts, however, will never be as painless as paying for an MP3.

Photo by Flickr user Andy Wright

Ray Lesniak, a New Jersey state senator, recently told the Star-Ledger that he plans on “placing my first bet at Monmouth racetrack on Sept. 8 for the Giants to beat the spread against the Lions on ‘Monday Night Football.’” He's demonstrating a hardcore commitment to his cause by saying he plans to commit what is currently a crime in New Jersey, the legalization of which is still heavily opposed by the likes of Chris Christie. But he's far from alone in trying to legitimize American sports betting.


Currently, the pastime Lesniak advocates comes complete with ex-mafiosi, uncles who threaten to break your legs, and goons who show up at your job and demand their cash. Where? Over the billions of servers and connections that make up the modern version of the Wild West.

The only type of legal sports betting in most US states is fantasy sports games. To be legal, the game must be (1) based on skill, (2) based on the results of multiple players across multiple real-world games, and (3) the prize amount must be fixed before the contest begins. There are a few federal laws that make just about everything outside of that illegal, so if you’re looking to bet on who’s going to win tonight’s Yankees game and whether the other time is going to lose by one run or three, you've entered the world of sports books, which are completely illegal outside of Nevada, Oregon, Montana, and Delaware.

For the average Joe who doesn’t have the time or resources to go to Las Vegas and sit around and bet on sports all day, there are plenty of lines—another way of saying "the spread," the odds of a team winning what and by how many points—they can bet against, right from their bedrooms using their smartphone or computer.

If it’s online it’s gotta be legal, right? Not quite.

Bookies and illegal betting have always existed and have mostly been controlled by the mafia—tropes we’ve seen in mass media since we were kids. What’s happening now is these guys wised up and moved their operations online. Take for example. Go ahead, click on it.


You’ll see Sportsbook, Poker, Casino, and Racebook at the top. When you click, you get this:

There’s no “start here” button or “check the lines” option. When you look around the website, you realize that even though there’s a box for logging in with a username and password, there’s no option to sign up.

The website claims to be a “leader in providing safe and secure online wagering" on NFL football, college football, horse racing, basketball, Major League Baseball, hockey, NASCAR, and boxing. Betting options include "spreads, totals, moneylines, quarter lines, half-time lines, futures, props and much more.” When you check out the terms and conditions, though, you see they are for “entertainment purposes only” and “may not be used in connection with any form of gambling or wagering.”

I talked to Les Barry*, who once used a site like this one, to find out how users get around the strange log-in system. Regular guys like Barry across Long Island, “people at the deli, real estate agents, shit like that,” who have some extra money—and who may or may not be connected to the mafia—set up websites like and act as sort of virtual bookies. They sit safely inside their homes and run the websites. In order to get people to go to their site to bet, they hire what are called “agents.”

Agents go out into the world and look for “people who want to bet.” They approach these people, let them know they can place sports bets, and if they’re interested, they’re given a special username and password so they can log in to the website directly. The idea is that this agent knows you directly, sort of recruited you for the site, and will oversee you, for lack of a better word. So once you get your special username and password, you log in, and to your delight, you already have $1,000 in credit to bet with. This is how they get you.


Winnings are paid and losses are collected at the end of each week, when the new lines come out. So you got your thousand dollars of fake internet credit and decide to bet a grand on the Dolphins vs. Jets game. Because you bet with your heart and chose the Dolphins, they lose and so do you, which means your fake internet money is gone and now you owe it to the real agent who introduced you to the website. That’s when things get kind of nasty.

Screenshot of Vegas Insider, the standard for oddsmakers

“They know down the line people are going to lose more money than they win. There were times when I would be up during the week—I’d be up two, three, or four thousand dollars—and because I was addicted, I would just keep betting and losing it all at the end of the week. You find yourself chasing—that’s what it’s called. You lose more, and then…” Barry explained over the phone, trailing off toward the end.

When it was time to pay up at the end of the week, he’d meet agents in shady locations like Starbucks. When Barry didn’t have the money, threats started coming in.

“There was one time, maybe four years ago, when I lost like six grand and I had half of it, and I thought I’d be all right. I go to the guy’s house to bring it to him, and he’s like, ‘If you don’t fucking have the other three fucking thousand dollars by next Friday, then that’s it,’ and sure enough, every day I was getting threats. Text messages, phone calls, it’s an ongoing nightmare. That’s just how it is.”


No longer involved in sports betting, Barry said the only sports bets he’d make these days would be in Vegas, where there is no credit system. While he did say it’s not as bad as the “old days” when people’s cars were getting destroyed and cousins would suddenly go missing, the money-retrieval process can be humiliating.

“They’ll show up at your job, they’ll embarrass you. They’ll show up at your house unannounced. You don’t need that. And it’s not like they’re just gonna forget.” They’ll just keep harassing you until you pay up.

“These guys were seriously pressing me, showing up at places where I was out at night and stuff. I paid it off and got past it. You don’t need to fucking go to the gym and see someone you owe money to.”

On the other hand, getting your winnings can be as much of a nightmare as paying for your losses. Like any legally questionable business, word of mouth and reputation keep them afloat. It's like when you’re looking for a new pot dealer, and you ask your other friends for a guy who's going to sell you a decent dimebag of Matanuska Thunder Fuck and isn’t going to rob you. This self-regulation doesn't always work.

“There was a time when I won thirty grand, and on a computer screen it said I was owed $30,000. I call the guy I signed up with and said, ‘You guys were supposed to pay me last Friday,’ and they tell you to go fuck yourself, and what do you do?”

There’s another side to this business that is happening entirely offshore, mostly in Costa Rica. As opposed to BetJupiter, websites like and are more legitimate. They don’t run on old-fashioned credit because bettors actually use a debit or credit card to make a bet (like in Vegas). You or I could sign up, and from New York to Florida, we could make sports bets all day long regardless of their legality. We wouldn’t have to worry about goons knocking on our door if our gambling got out of hand. We also wouldn’t be targeted by police, because cops don’t care about the junkie; they’re only concerned with the supplier.


As with any online business that's outside the law, authorities can only catch up so quickly. But they do eventually catch on. Barry told me a story about one of his friends who had $10,000 tied up with one of these offshore websites. One day out of nowhere, the website was shut down, and he has yet to recuperate his funds. But they still exist and are arguably thriving. Why is this? According to Lesniak, It’s an unenforceable law.

I spoke to Lesniak on the phone about this. "We can’t reach out to them or prosecute them because it’s off borders and outside of our jurisdiction," he told me.

The existing business is most likely entrenched, and likely defending the status quo however it can.

Barry was an 11th-hour source for this article. The first person I was going to speak to, Jaques* (a co-worker of mine for several years), took my phone call but clammed up when I started asking questions. He seemingly hung up on me, and when I called back he didn’t answer. A little while later, I got a phone call from someone demanding to know who I was, whom I worked for, and who was giving Jaques’s number out to me. Despite his Hollywood, Florida, area code, his thick accent told me he was a transplant from the New York/New Jersey area, and he wasn’t very happy to know that I was asking questions.

“It feeds the mouths of organized crime, and it benefits companies that are operating outside of the jurisdiction of the United States." Lesniak told me. "Shocking, by the way, that organized crime still exists in the United States, but it does."

*Names have been changed.

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