Jim is the name he uses as a bookie, not the name he uses at his other job, which is something he’d like to not talk about, because he’d like to keep that job. Jim is broad-chested and bearded and built like the kind of kid who’d have been a good linebacker in high school. Jim didn’t play football, though. Hockey was his sport. Still is. But hockey is terrible for betting. Football is basically perfect, Jim says. The week of the Super Bowl was going to be busy for him, but we aren't there yet. The Pro Bowl is playing on a television way back in the bar and some soccer is on up front, and Jim is sitting right in the middle, next to the kitchen, where the bar narrows and there’s a small window where the barkeeps pick up wings and fries mostly, and the line cooks tap a service bell when an order’s up. Sometimes the ring of the bell punctuates Jim’s sentences, and he pauses after the bell and sips from a glass of ale or a glass of water. Jim does not look like a cautious man but he acts like one. Overhead, over the drone of the kitchen and bar and even the games, a Buddy Holly record plays.
Jim started betting football seriously about five years ago. This was his own thing, he wasn’t running his book yet. But growing up Jim always had stupid little jobs, schemes he’d create for himself, like speakeasies run out of friends’ basements. That kind of thing. When he started betting more seriously he realized the big downside to the websites, and there are basically a million of them, is that it’s so hard to get your money out once you win—of course it’s hard to get your money out, Jim says, of course that’s how they keep you playing, and make money, the websites. Anyway he was like, "I’m just going to provide all my action through my own book. It started as a joke, really." So Jim started an account on a website, sportsbook.com, and told people they could bet through him, on this account, so they wouldn’t have to go through the bullshit of getting their money out, but if they won he’d take 10 percent of their winnings. And when they lost everything, they’d have to re-up the balance.
This went on for a little bit, more people, friends of friends, came along, and Jim did some loose math and figured if this many people were betting he could just be the house. That’s when it really started. "At this point, it was between seven and ten regular betters, like, every week they’d bet on a few games, at least a few hundred each, that was the magic number." Then the service bell goes ding.
All told today Jim has about 40 in his book—customers, friends of friends of friends. Half of those bet more than once a week, a hundred on this, a hundred on that. He pays out using PayPal but also "I have some people who are a little tin-foil-hat-y and just want cash." If you go down $250 to Jim, you have to pay it down, that is, you have to go back in to Jim. There’s some math here, and Jim threatens interest on late payments, 10 percent, but honestly almost everyone pays it down. He carries a little book with him, he pulls it out, a little black Moleskine where he keeps track of who’s in for what, flipping through the figures and tables quickly before slipping it back into his back pocket. People email their bets in, he writes it down. The only sort of client who is a pain are a few dudes who bet real heavily, a few grand a week, go up and down all the time, and are always floating between $300 up and $400 down. Unless they hit $500 down Jim’s not making anything off of that, and doing all kinds of calculations.
The ideal customers are the guys who are very fiscally responsible, bet a lot, and lose a lot. They never lose much, it's just, throughout the season, they’ll go down three times maybe. That’s $750 total. Each time they’re out $250 they just pay Jim back and start again. "There’s not really any amount of money someone can get into me for that’s worth me having someone beat them up. Like, I don’t care. In the worse case scenario someone goes down $500 and doesn’t pay me back. It’s not like I gave him a loan, in a weird way it’s money I didn’t even have. He got into me for it." Ding, sip, pause. "I try to be as friendly about it all as possible. It all is just through word of mouth. I’ve had a couple people just hit me up and I have no idea who they are but I have to check them out. I have to do a check, you know, that’s just good business. Certainly this is all illegal, but I’m just such small potatoes I don’t have any concerns about the cops coming after me, but, you know, it’s not my full-time business so I’d rather have fewer customers. It’s sort of like, there are the drug dealers who are really smart about it, who won’t talk to you unless they’ve met you, and there are others who’ll give their number to everybody. That’s just a bad business plan." Pause. Sip. "Not Fade Away" comes on.
"I had a few lunatics bet the Pro Bowl. Normally, the bets come during the week, starting Wednesday. You’re in your office, you’re bored, you start looking at the lines"—that’s the betting lines, the odds—"and sure on game day some people will bet on the coin flip and stupid little prop bets like that. Game day Sunday will be huge, a lot of last minute bets, live betting during quarters, halfs. Probably double what I do midseason, and midseason is probably $3,000 to $4,000 on a Sunday. But the funny thing about football, it’s so perfectly geared toward betting; the beginning of the season is more hectic than the end in a lot of ways. People are just hungry for it. There are more games, first of all, but also, it’s been hyped all summer.
"I had to pay out $2,500 once. A few guys love to bet on, like, college basketball, which makes it harder. I have to research the lines. Most of the guys are in their mid-20s, mid-30s, they’ve got some sort of full-time job, they chase that juice they get out of winning. I know some Teamsters who know some real bookies, and that’s not for me. If you recommended some dude to me who was 45 and had two kids and was, like, betting the mortgage I would just say no. I don’t need the money that badly. And I would feel too shitty if some dude lost his house because of me.
"I don’t have a particular endgame in mind but I know i can’t do this forever. It’s not even the time, really, which is like an hour a day, sometimes more. It’s more just like, I don’t have any serious long-term plans, but I do eventually hope to have something more like a normal life and not be out until four in the morning and doing drugs when I'm 45. And I never want to be like, I can’t read my imaginary kid a bedtime story because I’m staying up late looking at basketball scores because some dude made a bet."