Subscribe to Cigar Aficionado and receive the digital edition of our Premier issue FREE!

Email this page Print this page
Share this page

Living by the Book

Illegal Gambling Operations Handle Millions of Dollars Every Month
Michael Konik
From the Print Edition:
maduro issue, Winter 93/94

(continued from page 3)

Says Bobby, "The last thing we want is to draw undue attention to our office over a few thousand dollars. A couple of times out of 100 you're going to get screwed. That's probably the biggest drawback to making book."

Well, almost. The largest liability, of course, is that it's illegal. Several weeks before the commencement of the 1993 NFL season, the U.S. attorney in San Francisco, after a five-year investigation, cracked what the office believes to be the largest sports-betting ring in the country. The feds used telephone wiretaps, informants and IRS records. A federal grand jury returned a 59-count indictment against 26 members of a bookmaking syndicate that was thought to take in more than $1 billion a year from more than 10,000 bettors. These bookies, some of them Americans who worked out of a villa in the Dominican Republic, face felony charges of racketeering, money laundering and conspiracy, among other things.

Bobby's office in New York frequently used the Dominican connection as one of their "outs." If their books became too imbalanced or they simply wanted to bet with the Smart Money, the Manhattan bookies could call their wholesaler in Hispaniola. Seized telephone records surely contain Bobby's number. Yet he and his colleagues profess to be unfazed. "I know the figures sound huge. But really, we're small potatoes compared to a lot of other guys. Sure, the cops could bust us if they wanted to, probably. But they've got bigger fish to fry. I've heard some guys say that the over/under is four. If there's less than four people working in the room, it's a misdemeanor. More, a felony. I don't know, that's probably bullshit. But in some ways it makes sense: the bigger the office, the bigger the bust."

None of the bookies I spoke with has ever been charged with a felony. In fact, only one of them has ever been arrested. Ricky,* a 20-year veteran of the business who works in a rural area of the Midwest, has been collared four times. On each occasion he was charged with promoting gambling (a misdemeanor), fined $500 and given a suspended sentence.

Still, Bobby has contingency plans. "We've never had any problem," he says. "But we're prepared." His crew rents an alternate apartment, vacant except for preinstalled phone lines. "If we get busted, we move." The biggest risk Bobby takes isn't going to prison but gambling tens of thousands of dollars on the "hot side" or executing the weekly exchange of cash. "My exposure is minimal. I meet with my clients once a week with a paper bag of money tucked under my shirt. To me, that's the scariest part of this business. Walking around New York City with $20,000 bucks in $100 bills tucked into your shorts. Besides that, I don't worry. In fact," he says, "since I started making book, I never had it so good."

But not as good as Kelly.*

Except for the cellular phone that seems perpetually pinned to his ear, he appears to be an average citizen, a civic-minded pillar of his exclusive Southwestern community. And in many ways he is: the school playground boasts a shiny, red fire truck; the kiddie soccer league plays in stylish new uniforms and the library contains enough Macintoshes to start a small design firm--all thanks to Kelly's beneficence.

But the guy has his dark side. Whenever he goes to Vegas he regularly wins and loses six figures at the poker table. He bets $50,000 on one roll of the dice. And when he makes a sports bet, it's usually at the casino's highest limit. Granted, if he wins or loses $250,000 over a weekend, it's not going to have much effect on his lifestyle. Because Kelly, pillar of his community, is probably America's biggest bookie.

Working in a syndicate with four other well-financed partners, Kelly takes the bets nobody else will handle: when bookmakers around the country need to get a bet down, they call him. The minimum wager is $10,000--"anything else is too messy," he says, dead-pan--and the maximum is whatever Kelly feels comfortable with. "I generally don't like to take more than $200,000 on any one game, unless it's the Super Bowl, where all the information is totally out in the open. During the regular season, too many things can happen that I don't hear about in time. Maybe 10 minutes before the kickoff of a nothing game, the quarterback's wife has a miscarriage. Maybe the coach of a big favorite decides he's going to give his second-stringers a lot of playing time."

Though Kelly won't reveal how much action he typically handles over an NFL weekend, other bookies who bet with him estimate his volume at $6 million to $7 million. Multiply that by 16 regular season games, add in the playoffs, and you've got a bookie who can afford a few soccer uniforms. And that's not counting the baseball, basketball and hockey seasons. Because the numbers he deals with are so large, and, in practice, so unwieldy--carrying around $10,000 bucks in a suitcase is not easy--Kelly settles only two or three times a year, flying to Miami or Chicago or Seattle to rendezvous with clients. Or he'll sometimes use a "clearing man," a broker who arranges money transfers between two cities for a 5 percent commission. And other times he'll simply say, "give it to me when you see me." Which is a gentlemanly thing to do when sums equivalent to a congressional salary are involved.


< 1 2 3 4 5 >

Share |

You must be logged in to post a comment.

Log In If You're Already Registered At Cigar Aficionado Online

Forgot your password?

Not Registered Yet? Sign up–It's FREE.

FIND A RETAILER NEAR YOU

Search By:

JOIN THE CONVERSATION

    

Cigar Insider

Cigar Aficionado News Watch
A Free E-Mail Newsletter

Introducing a FREE newsletter from the editors of Cigar Aficionado!
Sign Up Today