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Degenerate, Inc.: The Paranoid and Obsessive Life of a Mid-Level Bookie

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"When you win and win big, there isn't a better feeling in the world — you're on cloud fuckin' thirty-nine," Steve says as he turns on his large TV, plops down on the reclining section of his oversized leather couch and pulls a laptop close. "You want to pop bottles of champagne in the basement because Hawaii won some game."

Steve stops briefly to check several cell phones pinging with non-stop incoming text messages.

"But when you lose, it's like you got kicked in the balls, twice," he says. "You get kicked in the balls, and they pick you up and kick you in the balls again as soon as you regain sensation."

Steve's a bookie and, according to some daydreams, a soon to be ex-bookie, but for now he's sitting in his living room commanding a mid-level operation on a college football Saturday. "This shit makes me smoke, drink and chew tobacco," he says about his life as he ponders moving south after his lease is up to start over. There are customers to be tended to now, however, and scores to watch. It's both what keeps him tethered to his gig and dreaming of an end — the rush, the cash, the line manipulations, the fights, the all-consuming record keeping, the hindrances to normal life, the paranoia, the sleepless nights and the degenerates that keep him in action.

Steve, in his mid-twenties, and Luke, the older brother of an old friend, have built a healthy business for themselves on the other side of the law — a solid client base, steady income — and like any other business, there are ups and downs and headaches, though some are peculiarly unique to this line of work. And for a long time, they were on the other side of the gambling equation, until a crushing downward spiral of debt convinced them to switch sides five years ago and to take bets instead of making them.

***

Steve handles the day-to-day nuts and bolts of the operation and receives a flat monthly salary for his work. Small bonuses after particularly prosperous months are delivered, larger bonuses after particularly prosperous years. He and Luke have paired up since 2008 to take bets on four leagues — NFL, NBA, NCAA football and basketball — pulling in tens of thousands of dollars a year from a consistent bettor base that includes friends, friends of friends, friends of friends of friends and the occasional guy from the bar.

Among the trove of construction workers, landscapers, lawyers, local business owners and other random guys they take action from is an agent for several Browns players, who happens to owe them several thousand dollars (which is significantly less than the $40,000 he owed before he started making payments) and a broadcaster who covers the Browns. And even if they're not betting with your book, you get to know the folks who like action, even if they're taking it to the guy up the street. Steve talks about a former Indians pitcher, who retired not all that long ago, who likes to bet, but doesn't elaborate on if he bet on baseball while active in MLB or if he took his bets.

Steve's a self-described "degenerate" gambling addict, but is also an obsessively accurate record keeper: The detailed spreadsheet he uses to track every single move from the 50 or 60 people who bet with him ensures the balances are right at all times and also provides data he uses to adjust the lines he sets for future games. He checks the lines Vegas sets for the games, adjusts them based on what he thinks his clients will pick, sends a text to every single client a half hour before games starts and then records each pick the moment they come in.

Luke handles the money, meets with the bettors during the week to collect or pay out, calls the shots about who can bet with them, works out deals for people who fall too far behind in repaying debt, and pays Steve for the work. They both have "legitimate" jobs that can fund the necessities; the betting business pays for everything else and a few things more.

They were on the opposite side of the gambling spectrum five years ago. Steve was going to community college and living in a house with Luke and Luke's younger brother. They both were thousands of dollars in debt to bookies.

"We had a little bit of a gambling problem," Steve says. "We gambled before this together. We lost, pretty bad."

They were hemorrhaging money on two fronts. First, they were paying steep fees and commissions to call professional handicappers like Adam Meyer (known as "Adam Wins") and someone known as "Mikey Wins" to get their advice, and then when that advice would be wrong, they'd have to pay the bookies they were using as well as the fees.

"They fucking suck. You lose with those guys," Steve says. "Based on what you pay him, you get the better play. He'll tell you five plays a month or five plays a week, whatever it is. He'll be like, 'Take the Browns over the Dolphins this week. The Browns are definitely going to cover by three, and take the Packers over whoever.' He'll tell you he has $40,000 on this game and $80,000 on that game, but you don't know what the fucking guy's really got. And then he's like, 'We'll keep track and if you make X amount of dollars in one month, then you pay me this.'"

Those bets are supposed to come through — that's what you're paying for.

"You're giving these guys credit card numbers over the phone," Steve says. "I've wired money to New York; $1800 in cash I've thrown down on the counter at Western Union to wire the money to 'Juanita Lopez' in New York City. And we didn't even win money with that; we lost it. It was one of those things where why would we continue to gamble. We're paying these guys to give us winners and we're still losing."

Steve and Luke were $20,000 in debt to bookies when they decided to make a change. You can't bet your way out of betting debt. All Steve had then was the money from his minimum wage job, student loans and what he borrowed from his unsuspecting family. He cried himself to sleep wondering what he'd have to sell next to dig himself out of the hole he gambled himself into.

"Me and Steve, we both thought we knew more than Vegas so we thought we'd just start betting big with our bookies and then on the side, we just take a little action," says Luke. "With our bookies, if we lost, we decided we'd just pay that off with the action we were taking in. But we got really, really in the hole with our bookie and Steve was crying a lot."

Steve interrupts: "I went to bed every night thinking, 'Okay, I have to sell this now.'"

"We were probably $20,000 down with our guys," Luke continues. "I took out a second mortgage and then paid off my guys, but it kept rolling until we were in so much trouble that it finally switched. I think it was Steve finally giving up that finally turned me. He was asking to borrow money from his mom and grandmother. When we stopped, we were able to concentrate a lot more on just the booking side of it."

***

Luke took the lead. He was a few years older, put up the money to fund the operation (if you're going to take bets, you damn well need the money to pay out immediately if the bettors hypothetically win every game in a given week) and knew the guys he could swipe from other bookies.

"He's the money, financially, always has been." Steve says. "I worked for him for the first three years, basically, to pay off my debts from when we lost gambling."

The next step was finding the initial betting base, which turned out to be pretty easy. Degenerate gamblers tend to know other degenerate gamblers. Ben — who now shares an apartment with Steve, grew up with him and Luke in the same Cleveland suburb they're in now, has recruited people to join, and sometimes helps out with the operation — says Luke is the type of guy who knows everybody. He's the kind of guy who still keeps up with old high school football teammates and knows the kind of people who put money on games.

"A lot of those guys were betting through the guys that Luke was betting through," says Ben. "But Luke is a nice guy, he can go, 'I'm your friend, why don't you just bet through me?' The thing Luke has on his side is he had a large group of people he already knew."

"You just have to find degenerates that want to gamble," Steve says. "That's a serious thing, I'm not being funny. We knew guys that liked to gamble, so it's just like, 'Why don't you make your plays with me?' Booking business is all word-of-mouth referral and shady people."

And it's knowing how to hook them in. Like a cable company's free-HBO-for-a-year promotion, Luke and Steve knew they'd have to set more gambler-friendly lines at the beginning to hook them in before normalizing everything and raking in the profit.

"We started with like 10 guys and, to be honest, we put ourselves out there the first couple years," he says. "We would lower lines, we would move lines so that they would be more favorable for them and people would want to bet with us. Like if the Packers were playing the Niners and the Packers were -7.5, for the first couple years we'd make it -6.5. That might not sound like a lot, but it is."

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