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

"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."

They would also lower the "juice" (also known as "the vig") — the commission a bookie gets for taking a bet — to try to get guys to jump ship. It worked.

Do bettors realize they're not getting as good lines as they once were?

"I think the mind of a degenerate gambler is only in the present week," Steve says. "It gained us clients and we only did that for the first couple years but it got us guys. Casinos make their slot machines pay out more to get people in, and then they tighten them up a little bit. That's what we did. We got guys in and because of it, the web extended. Then we went back to normal and started moving lines against what people were taking, which made it much more lucrative."

Their base has now expanded five or six times from where it started.

"It's all kind of spiderwebbed out and we try to keep it so that everybody's at least tied back to somebody who's tied back to somebody who's tied back to us, so we can hold them accountable for him," Steve says. "Like I know you through him, so if you owe me money, I'd go to him and say, 'Dude, your fucking boy owes me $1,000, you need to get on him because I'm holding you responsible for that bullshit.' And after a while and you're good, we meet a couple times, have a beer and bullshit, now we're good, and you can tell me you got a guy, and if he owes me $200, it's on you. If we have no problems, you're good with me and I'm good with you, we meet a couple times and pay on time, then we're set."

Ben recruited a group of steady bettors for Steve several years ago when he was off playing college football. He found out some of his teammates were betting on other college football games through an assistant coach — about as clear of an NCAA violation as it gets.

"We'd come in from pre-game warmups and these guys would be checking their phones. At halftime, we'd come to the locker room and they'd check again," Ben says. "I told them I know somebody credible, they run it like a business and they run it very efficiently." Plus, getting busted was less likely if they weren't running action through their coach. So they switched. And it turns out rich kids in college are good customers.

"The kids like that, the younger kids we know who come from richer families, go to mommy and daddy for help with money for 'books,'" he says. "But that money for books is to pay off gambling debt. It happens."

Outside of the friend-of-a-friend network, there's other ways to recruit new clients. For example, you might find a new pal sitting at the bar. You know, that one one guy sitting by himself, wearing an Indians hat or Browns jersey but anxiously and attentively watching the blowout end of a regionally irrelevant game.

Steve explains: "You go to a bar and you can tell, you can just tell the guy's gambling on games, you can just fucking tell. The guy's paying attention to the game nobody should give a shit about, that's the first telltale sign. That guy has some money on it. A Dolphins-Rams game, who gives a shit about a Dolphins-Rams game? But some guy sitting at a BW3 is watching it at the bar and he's angry about why they're running a draw on 3rd-and-six. You walk over and ask who they got, you lead them into it. He'd say, 'Oh, I got the Rams.' 'I got the Rams too. What's your line?' You just ask them what their line is, they'll tell you. He says he got a -6. You tell them you got -5.5: 'You got a bad book.' It's just one thing like that and all of a sudden you got a new guy. You give them your phone number like you're picking up a chick."

***

With a large customer base and years of their betting patterns built up to analyze, Steve knows what he needs to know to keep the money come rolling in. The bookmaker's goal is to adjust the line to get an equal amount of money on one team as they do on the other, then just profiting off the commission (the "juice"/"vig") the loser pays to place the bet. If you get people betting $1,000 on Team A and a $1,000 on Team B, that's an automatic profit of $100 from the 10-percent juice the losers have to pay. That's what you want: The more even the distribution of money, the less you risk.

Much of the weekend during the college and pro football season is taken up by Steve on his couch, computer open to the spreadsheets he keeps on each client and the website that curates all of the betting trends of the eight major Vegas casinos and online sportsbooks that he uses to set his own lines, and typing on the prepaid Blackberry (registered under a phony name) he uses to send out his lines and take in his action. The Vegas lines are a guidepost, but his clients' previous plays — logged on his computer — ultimately dictate what he sends out go to the group a half hour before games begin.

It's all a guessing game based on what he thinks people might decide to bet on and the side they'll pick when it happens. He has a one-time shot to get it right, one group text to send out that can sway five figures in one night. "Once it kicks off, we always send each other texts saying 'let's hope we're right,'" Steve says about communication with Luke during games.

"It's knowledge of what your guys have taken in the past. You have to pay attention to trends," Steve says. "If you have 20 guys who take the Broncos every week, you move the Broncos line a little more, make them cover an extra point, force them to take the other team. That's all tracked: I have to know these things or I can't do my job. Every week, I need to know that for the past five weeks he's taken these teams, I need to know if he takes home dogs, road favorites, all that shit. You have to know what people are going to take. I know for a fact 30 people are going to take the over [total point total] for the Saints game every single week. I know that they're just going to do it. That over, every week, is going to be moved up a half a point."

The line moving is most obvious for Browns and Ohio State games. There are people who are going to "bet with their heart" regardless of the line, so he has to move the nationally determined line significantly more to compensate for the many clients who always want to pick the home team to give them an incentive to go with the opponent. It's a bluff: If people saw how he's moving the lines against the Browns and Ohio State — and other traditional popular picks like Oregon football, the Broncos and Saints — and took the other teams, they'd win more often than not. But they don't.

"None of them will fucking do it, none of them will call my bluff," he laughs. "If I'm going to move it, call my fucking bluff. And none of them do it. They just continue to fall into the pattern, so why wouldn't I do it?"

***

Northwestern was down 34-30 to Ohio State when they lined up on their own 8-yard-line with just enough time for one final desperate play to beat the Buckeyes on Oct. 5. It was a nationally televised back-and-forth matchup of two previously unbeaten teams, but people who put money on the Buckeyes were not celebrating: Vegas set the line at seven points, so the impending four-point victory after the final play would mean they'd lose their money.

Watching excitedly from his apartment, Steve was already documenting the spoils of his victory in the spreadsheets: Nearly everybody who bet with him put money on Ohio State, despite the slightly higher line he sent out. Even in Vegas, with the line increasing from 5.5 points to at least 7 as the game approached, there was significantly more money on the Buckeyes than Northwestern. A lot more. All Northwestern had to do was not turn the ball over and give up a touchdown on that final play and both Steve and the Vegas casinos would be raking in one of the biggest wins of the season.

But then something crazy happened: A Northwestern player fumbled a pitch and the ball trickled into the Northwestern endzone. A Buckeye defensive lineman pounced on the ball as the game clock hit all zeros. Touchdown. Ohio State's 34-30 victory suddenly became a 40-30 victory. They covered the line. It meant nothing to the outcome of the game, but even broadcaster Brent Musburger knew the implications went far beyond that:

"Scramble for the ball, touchdown Ohio State!" he exclaimed on the broadcast. "And you know what, there are some folks who are celebrating and others who are saying, 'You gotta be kidding me.'"

His broadcast partner Kirk Herbstreit asked: "Who's celebrating, Ohio State fans?"

"They were celebrating early! There are some numbers crunchers who... " Musberger chuckled a little bit. "Oh my goodness. Oh my goodness."

It's almost like Musburger was talking directly to Steve with that comment, as he tossed his laptop to the ground the moment Ohio State's defense fell on the ball in the endzone.

"Anything other than that, I win," he recalls. "We lost five figures on that play; Vegas lost $100 million on that touchdown. I broke my computer after that. I threw it mostly because I had everything entered already because the chance of that happening were like one in a billion."

But sometimes fluke plays — the ones that have nothing to do with the result of the game but somehow end up changing the result of the bet — work in his favor. He recalls the blowout end of an NBA game a few weeks ago when a player was just dribbling out the clock and tossed a shot up as a goof.

"A guy sank a pointless three-pointer as time expired on some meaningless NBA game to cover the line," he says. "And we made more than a grand on that pointless three."

***

Steve and Luke run a profitable operation together — one that got them both out of that suffocating and soul-crushing gambling debt — but the major friction between them now revolves around different philosophies on handling the customers who are now in significant debt to them.

Luke's too nice, too friendly, too quick to forgive so much debt from someone who owes thousands of dollars and shouldn't allow people to place bets when they owe money, Steve says. He gets angry having to take bets from "asshole degenerate" bettors he knows got a deal on their old debt.

"I give Luke shit all the time because he's your best friend, your next-door neighbor kind of guy," Steve says. "Because Luke builds these budd-buddy relationships with these guys, these guys are willing to work with him. He gives them enough of the fucking carrot, he puts that carrot out in front of them and lets them work toward it, then get a little bit of it. He gets paid about half of what he's owed and then still lets them make plays. He'll let them do shit like that, but for nine months of the year those are the guys I have to to deal with on a day-to-day basis. I have to communicate with these guys nonstop."

Ben, his roommate, mentions that Luke's amiability is effective in getting money for a bookie who refuses to break kneecaps to "send a message" to debtors. "You see in the movies where a bookie has his meat hunt you down or kick your ass if you don't pay, but it's not like that," Ben says. "They play the guilt trip. It's like, 'Come on, man. You've been running, just pay me a little bit. I'll work out a deal with you if you pay me this, or I'll cut it 25 percent.'"

Steve's still on the fence about that tactic: "'Dude, you can't be everybody's friend because that's why people don't respect us,' I tell him. But on the other side, we've had people pay off debts over the course of the year because they respect him enough and don't want to do that to him. It walks a fine line, the approach he takes, and I don't always agree with it, but it works to an extent. We're not going to break your knuckles. I've had to fall in line and take a similar approach, an 'I'll be your buddy' kind of thing."

The agent for a couple of Browns players once owed them $40,000; he only owes them $6,000 now.

***

Steve is making money now, and though his past fears about repaying bookies have disappeared, they've been replaced by the nearly constant paranoia that he's going to get busted by the IRS or police.

There are endless scenarios he runs through his head: If one of his guys gets arrested for something else, would they dime him out to get a better deal? Could the new person he added be an undercover agent? Is his cell phone being tracked via GPS? Are the cops going to bust down the door at his job and take him away?

"Everyday it's fucking non-stop worrying," he says. "You just don't know. We're talking about degenerates, seedy degenerates, guys that have lost their wives because they have gambling problems, guys that have separate bank accounts. God forbid Johnny has a coke problem too, you don't know. Some dude could get pulled over driving drunk and they could go through his phone and see his shit. You don't know, everyday, you don't know."

And then there's the difficulty in stringing together anything resembling a normal social life. Steve's entire operation is based around sending lines out a half hour before games and immediately logging everything into his spreadsheet. It doesn't leave much room for romantic relationships with women who'd rather go out and do things on the weekends and not plan their schedules around the time of the Western Michigan vs. Ball State kickoff.

It takes him from his friends and family too. Steve recalls how he had to leave a New Year's Eve party last year at a friend's apartment so he could log onto the computer and send out balances to clients just after midnight, so people could see what they owed from that day's NFL games before the next day's NCAA bowl games. A week earlier, he had to leave his family's Christmas Eve gathering to send out balances for the same reason.

"What it's like now is not how it's supposed to be," Ben says. "It wasn't supposed to be Steve having to leave family on Christmas Eve to go sit in his car for 45 minutes because there's a bowl game and he has to send shit out, or having to take breaks at work because he has to send shit out. When Steve had a girlfriend, it was a conflict because she wanted to go do things on the weekend and he had to get things done. He's an everyday person who not only has an obligation to his boss, but the 50 other people betting with him, because if the shit isn't done the exact same way as the past five years, people freak out."

Steve interrupts: "Yeah, if all the lines are not not out exactly 30 minutes before the games, I'll get all these text messages within five minutes - a string of question marks, maybe. 'Where the fuck they at?' 'Where are the lines?' 'You up?' 'You alive?' 'What's going on?' I've got a life to live too. Like, at work, I have to schedule my breaks around this shit."

But would he do it again if he could go back to 2008?

"Yeah, because it takes care of my gambling itch," he says. "See, gambling degenerates, you get an itch."

Are you a degenerate?

"Oh yeah," he says. "I have a gambling problem, and this cures it. I don't need to gamble because of this. Otherwise I'd gamble... I am gambling, essentially, but I get paid at the end of the day. I get paid more if we win, but I get paid, regardless, at the end of the day."

***

Back in late summer, Steve and Ben were talking about moving out of their apartment in the winter when their lease ended. The bookie business was getting too much for Steve and he wasn't getting paid nearly enough, he said, to justify the hit his social life was taking. Ben would take over for him; Steve would head south.

But as the months came and went, the talk died down. The deadline came and went with no mention by Steve.

You don't escape your bookie's financial stranglehold by working a minimum wage job, and you don't stop being a bookie to return to one.

*The names in this story have been changed to protect the subjects' identities.

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