Show him the money

A Chicago-area bookie provides a glimpse into ‘the life’

By Trent Modglin

The budding stages of this operation, the thrill of it all, started back in high school, when he and his friends used to distribute parlay cards to fellow students. Even some of the young teachers were involved. They’d make $200-400 a week typically. At Super Bowl time, maybe $1,000. Not bad for a bunch of kids. Beats asking if someone wanted fries with that.

Now, it’s on a slightly larger scale for “Dave,” as we’ll call him, a resident bookie feeding Chicago’s craving to gamble. He has a regular job, but it doesn’t bring him perks like this.

He always eats out, barely knows what to do at the grocery store unless his girlfriend is there. Everything at his house is brand new. He took his entire family to Vegas last spring for his parents’ birthdays. Rented out an entire floor of a posh hotel. When he visits Vegas with his buddies, bar bills can reach $1,000 a day. They started tipping $100 a day to make sure they have the best chairs by the pool each afternoon.

Dave is never caught without a certain amount in his pockets. His own bets, on games, start at $500. At the tables in Vegas, it’s hundreds per hand, easy. He and his pals reside in the VIP lounge at casinos. He used to look at the people inside the velvet ropes differently. Now he’s one of them and doesn’t think anything of it. He’s not exactly sure when the transition was, when paying $200 for a $25 bottle of Absolut vodka would have seemed asinine.

“As young guys, I think we lead an extraordinary lifestyle,” he says of himself and his partners. “I don’t know too many guys like us that own s--- like we own or go out to the places we do. The best of everything. You’re paying, but so what? It’s really a joke.”

Dave, his partner and his partner’s partners all own sizable houses near Chicago, and they’re young. They share three properties in Florida. Dave has a 50-inch TV at his house that cuts off the scrolling scores at the bottom. He can’t figure out how to fix it, and he’s not happy about it.

He can’t go to movies unless he knows the theaters have a certain kind of plush seats. He won’t go to a restaurant without valet parking, and he wants his ride parked right in front. The tab, for whatever, is picked up by Dave and his partner. It was $1,200 for a dinner for six last weekend in downtown Chicago.

A woman, not so long ago, actually convinced him to leave the life. She had him in her corner for nine whole months. But the life won. He hated not having it. He got accustomed to having his pockets lined with money. Everything is better with money. “It’s not the same, just trying to live off a regular job,” he says. “It doesn’t cut it. Not for me. Not for my lifestyle at least.”

She liked being treated like a queen, but she wanted him to herself, or something close, something reasonable. She couldn’t get used to the hours he kept. But if you’re a bookie, and you get a call at midnight from a guy who owes you $10,000, you’re putting some jeans on and grabbing a jacket.

“A gambler, when they have the money, they’re gonna give it to you,” Dave says. “If not, they’re not gonna call you. But if you get the call, you gotta go.”

When you have more than 100 clients, it’s not only hard to lose, it’s hard not to find connections. Want something done to your house, new windows or a wood floor? Make a call. A deal on an SUV? Make a call. Courtside seats when the Lakers come to town? Sox playoff tickets? Done. He’s got a ticket guy he can’t get bad tickets from. Some are favors, other times it’s to help pay off debts.

His 100-plus client list for football drops to 75 or so during basketball season, then down to fewer than 50 for a baseball-filled summer. During Super Bowl week, there are at least 25 more people betting than usual. They come out of the woodwork.

People bet by calling a pager number, only the actual pager doesn’t really exist. When you call, you get a recording with a list of updated spreads for that week’s games and then an opportunity to leave a message, account number first. Dave and his partner used to handle it all themselves but now pay someone they trust $500 a week to transfer all the bets onto a legal pad, and he goes through a bunch of legal pads. They keep messages for a day or more to avoid discrepancies. Bets over $2,000 have to be given to a live voice on the other end. Dave’s cell phone bill starts at about $500 a month.

Voices on the recordings can sound more and more drunk as the day wears on. They start out betting $50 for the early games and can creep up to $300 pretty easily when they’re losing later in the day, all while the slurring of words increases. Then they begin to move to the late games out West as the hole deepens, trying to make it all up in one fell swoop. Then comes the final wager, maybe for $500. They may have little or no idea what they’re saying.

“The latest game is Hawaii. If they’re betting on Hawaii at midnight, I know they’re down money,” Dave says with a chuckle dripping with apathy. “I don’t even need to look at the books. It’s almost a proven fact.”

There is lots of driving involved in being a bookie. One day he’s heading to the Chicago Board of Trade, trying to round up all the suits at lunchtime, then he’s off to a construction site. When you owe, as a bookie, the clients come to you. But when you’re owed, you’ve got to go to them. Funny how that works.

Bookies don’t just take bets, they also throw down money, quite regularly actually. It’s called “picking off” other bookies, taking advantage of information before they change lines. And everyone does it. Dave and his guys are betting right now through an old veteran of the business, one who, foolishly, usually doesn’t tweak lines after he posts them. Playing the line movement can be awfully profitable, especially if it’s a significant move.

In the business, they’re called “sharpies,” guys with the inside track, guys who jump all over games once the lines hedge one way or another. Dave has fallen victim himself.

“He would wait until it moved a point or a half a point, and bam, he was on it like white on rice,” he says. Dave is speaking of Jerry, from Indiana, another bookie for sure, who played the system and played it well. Took them for about $240,000. What a run he was on. Never leveled off. The one time they thought they had him, when he lost $80,000 one week, he fired back with eight straight winners to pull even the next week. When they would meet him to deliver his winnings, he would brag about his new Corvette.

It got so bad they started taking his picks and putting their own money on them in an offshore account, just to recoup some of the cash he was taking from them. They ended up earning about $100,000 of it back. “That’s how bad he was beating us,” Dave says. “It was terrible. That was the first smart thing we did.”

The second smart thing was finally cutting Jerry off. People told Dave to do so earlier, but he and his partner assumed a bad stretch was inevitable, like it is for everyone else.

If they see a disparity among their clients, like $30,000 more on the Packers to cover against the Eagles, they’ll offset it by changing the line in the Packers’ favor or betting some of their own money, say $15,000, on Green Bay, usually with other unknowing bookies or in an offshore service. They never want to get hammered. (Remember, bookies are content to have an equal number of gamblers on both sides of a game so they can get out with the 10-percent juice the losers pay.)

Although it’s not like it was back in the day, when the FBI came kicking in doors, you still have to take precautions in this line of work. Dave and his partner, not wanting to leave a paper trail, don’t own credit cards, which makes life difficult when it comes to reservations for a hotel in Vegas or concert tickets in the city. But once Dave gets to where he’s going, cash, to no one’s surprise, is treated as well as anything.

A cross-cut shredder, for all those legal pads, is vital. Don’t tell people your business. Plenty of people already know what you do, and they’ll always have something to hold over you. People get jealous. Don’t ever have too much evidence at your house. Cops know everywhere to look. Dave has heard stories about Cheerios boxes and fake safes and digging in the backyard. Be smart. Don’t take bets in front of anyone. Don’t do anything on your house phone. Change your phone numbers at least once a year. Put nothing on a computer. Surround yourself with good people. Dave’s lawyer bets with him. His accountant grew up with him. Always be looking ahead.

Things have changed in other ways too. The business has taken on a softer side of sorts. You can’t go and beat guys up anymore, threaten them with a baseball bat to the kneecaps and such. But you can skirt the edges.

When one guy, a real big talker, was down $40,000 and not lining up to pay, his partner paid a pizza delivery guy for his address, delivered a pizza himself, and, well, smacked half of it out of him. “With something like that, if you’re owed that kind of money, you’re not going to get it all unless it’s a true player who you know or who’s got that kind of trump,” says Dave with a shrug of the shoulders. “If not, you’re going to get a deal, like a plea bargain.” Unless a guy who owed a lot of money to a lot of people leaves for Italy, which happened, not too long after Dave slammed on his brakes and left his girlfriend in the car to go talk to him on his front steps, fists-around-the-collar style.

Friendships are ruined in this business. I wanted to ask Dave if that’s the case, but he beat me to it. A good friend he knew since grammar school had collected $60,000 off them. The guy invested his winnings in a condo before busting hard. He used to be a big spender, ordering champagne all the time, enjoying the good life. “Now he won’t call me, he won’t talk to me,” Dave says. “I’m not gonna ever do nothing to him, but you know what I mean? It hurt my feelings more than anything.”

Guys with families are especially tough to deal with. What can you do? Dave has had to cut deals with friends to get them off the hook. They owe him $20,000, he lets them off at $7,000 and then shuts them down. Sometimes they try to come back, usually at Super Bowl time.

“I know the inside and out of this business, and if you take a $15,000 or $30,000 bet like I did the other day on New England, you gotta know that these guys are good for it,” Dave says. “Even if they say, ‘I promise I will,’ I’ve heard that a thousand times.”

If you’re looking for a sense of guilt, guilt over his business or his lifestyle, you’d best start looking elsewhere.

“These guys are old enough to make their own decisions,” he says. “You can’t be their mom or dad. They know what they’re doing. It’s like any addiction, man; it’s like an alcohol problem or a cigarette problem. That’s how I look at it.”

Dave doesn’t always watch the games. But that doesn’t mean he isn’t in tune with what’s going on. “Every day when I check the scores, my heart beats fast,” he says. “You can feel it because you got big money out there.”

And he doesn’t seem worried about his big-money enterprise drawing him into trouble, or getting pinched, as street lingo goes. But, like everything else, it’s not like it was, Dave says. “It’s not syndicated. You get a ticket now. Illegal gambling — it’s like a misdemeanor.”

There is a time when he’ll call it quits and leave the life. A time when he’ll leave the velvet ropes, the drunken messages for bets on Hawaii, the $1,200 dinners, the line moving, the plea bargains, all of it behind. Leave it to someone else. I assume that. He doesn’t say it. Right now, he can’t see it in the near future. Maybe 10, 15 years, he says. I look at him, unconvinced for the first time all day. You sure about that? He smiles, his eyebrows soar to the top of his forehead. “No, I don’t know that. As long as it’s good, I’ll stay in. I’m just enjoying the ride.”

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