The Rise and Fall of Internet Sports Bookie and Poker Pro James Giordano

From Bluff magazine to court, James Giordano was wired for success until Queens prosecutors captured him in their web

Last Wednesday, a former bookmaker named James Giordano stood up in a Queens courtroom to be sentenced for promoting illegal gambling.

Giordano, 55, was indicted in 2006 for running a sports betting website in the Caribbean that banked millions of dollars in bets from dozens of U.S.-based bookies and thousands of individual gamblers. Just over three years later, the case was finally at an end.

The hearing was brief, a routine matter of the kind that takes place in courtrooms all the time, and the sentence—five months in prison—hardly seemed noteworthy.

James Giordano's poker playing got him into Bluff magazine.
Bluff magazine
James Giordano's poker playing got him into Bluff magazine.
Al Goldstein: “I thought porn wasn’t going to last.”
Al Goldstein: “I thought porn wasn’t going to last.”

But for those who have followed Giordano's case, his sentencing was a characteristically ambiguous end to an epic battle being fought over your right to place a wager on the Internet.

It's a legal conflict that the United States is fighting all over the world with foreign countries that have repeatedly and angrily told off the American government. Other nations resent what they see as America's hypocrisy about what is, and isn't, the proper venue for placing a bet on a horse or a football team or a hand of poker, bringing us into conflict with entities as varied as tiny Antigua and the entire European Union.

There's no end in sight to that war, but the particular skirmish wrapping up last week at the Queens courthouse involved characters more close to home: a local bookie nicknamed Slippery Pete, another man whose career as a New York Mets scout ended indisgrace, a couple of reputed minor league wiseguys, some mouthy lawyers, and a colorful judge who, at one point, invoked Nevada's Bunny Ranch whorehouse to make a point.

The slate of players even includes the eccentric pornographer, Al Goldstein.

But in the starring role is a gentleman-bookie turned professional poker player who got his start watching bets laid down in the aisles of a Long Island supermarket. And you don't get from there to running a multimillion-dollar bookie joint in Costa Rica without some fast moves and moxie. So try to keep up.

In 1974, Jimmy Giordano was newly married. He had left college after one year and was looking for a course in life. His father-in-law planned to start a chain of pharmacies, and asked Giordano to manage the drug counter and the non-food aisles in a Pathmark supermarket to gain experience.

It was at the Pathmark that he first witnessed a curious ritual. Over the week, the produce manager took bets on boxing matches and football games from other employees. Every Wednesday, he'd make a phone call and then hand off the cash to a small, Italian-looking guy.

After watching this for a few weeks, Giordano says, he asked the produce manager a question: Why was he bothering to hand over the money? Why didn't he just handle the bets himself rather than call in someone else?

"It seems to me that if you eliminate the phone call, you can keep the money. That was my logic," Giordano says in the first news interview he has ever given.

He had found his calling. He ditched the pharmacy idea and went into business with the produce guy, starting a bookmaking operation of their own. Later on, he and another partner worked the business for another 11 years or so.

Despite the risk of arrest and jail, Giordano says he thought of his job as just that.

"My wife and I, we were clean-cut kids from South Merrick and South Bellmore, churchgoing. It just became a business. We never looked at it as being something terrible," he says. "You did your best to get your money, but we never got involved with thuggery or usury. We kept it clean."

Giordano's first arrest was in Suffolk County in 1991. He avoided jail time, but paid a fine.

Undaunted, he continued the business. By the mid-1990s, he had about 600 customers during football season. He was no schlub operating from a barstool, either; he rented space in an office building—there was no sign on the door—and used a phone system that rolled calls over so no one got a busy signal.

"I always had an aptitude for numbers," he says. "If you're going from here to there, I'll be able to tell you how many red cars you'll see. I'll give you odds that you might actually be willing to bet on."

In 1996, Nassau County authorities arrested him again. And again, he avoided jail time by pleading guilty and paying a fine.

But this second arrest, he says, gave him pause.

Firmly against the prospect of a third collaring, Giordano figured there had to be a better way. Internet gambling was in its infancy and promised a slick way to rake in a lot of cash. But, he insists, what drew him to it was the prospect of finding a way to do his work without the fear of incarceration.

On the Internet, and working in a country with different notions about gambling, Giordano figured there had to be a way to do things legally.

Proof that he wanted to do things as legitimately as possible? He points out that he hired Nassau County lawyer Peter Bee, a former mayor of Garden City, Long Island, to study U.S. law on online wagering before he set up shop.

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