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

Brave said that was against the law.

"The only thing [in that example] that went on in Queens County was collecting a debt that occurred in Las Vegas," the judge said.

Brave insisted that would be a crime.

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.”

"The wager took place in Vegas; the debt occurred in Vegas," the judge pointed out. But the prosecutor wouldn't budge.

"What about the New York State Lottery and Mega Millions—are they promoting gambling?" the judge asked.

Brave said no.

"They are telling everyone, 'Please gamble,' " the judge pointed out.

"That's a legalized form of [gambling]," Brave answered.

"So it's legalized in Vegas. That's exactly my point," Schulman said.

Brave still wouldn't concede. "It is still advancing and profiting from gambling even though it happened where the conduct was legal," he said.

"Gambling is legal in Queens County when Aqueduct is open," the judge responded.

Then the judge took another tack, and proposed a hypothetical situation involving a Queens resident going to Nevada to patronize the Bunny Ranch, a well-known legal brothel once featured on a cable-TV series.

"What if the guy charges $10,000 worth of services of a prostitution ring and then stopped payment on a credit card. Do you mean they can't come here and sue in our courts because prostitution is illegal in New York?"

Brave replied, "I think we're getting far afield."

In the end, Schulman reduced Giordano's bail to $750,000, calling the original amount of $5 million "an abuse of discretion." Giordano left custody after 10 months in jail while his legal case grinded on.

His attorneys argued that the wiretaps should be suppressed because Queens investigators had no business listening in on Costa Rican deals that were legal in that country. Brown's office says a New York judge signed off on the warrant to search the computers in Costa Rica. The office didn't need approval from the Costa Rican government. One of Giordano's attorneys, Paul Testaverde, went after the judge, Stephen Knopf, in his criminal case, accusing him of conspiring with prosecutors to suppress Giordano's rights and, at times, raving at Knopf, telling him he should kick himself off the case "based on the outrageous actions of Your Honor in this case, based on the illegal actions of Your Honor."

Knopf ignored him.

But as 2009 unfolded, everyone in the case seemed to dread the prospect of a trial, which would have been lengthy and technically daunting. Knopf began pushing both sides to come to some kind of plea agreement. Testaverde faded to the background as other Giordano attorneys took control. One of them was Becher, who had been involved in one of the early Internet gaming companies, a firm based in Panama that was indicted by the feds in 1998. The company paid $1.2 million in fines.

"We had done everything to be transparent," Becher recalls. "We paid taxes, and we declared our earnings. And I think at the end of the day, the government realized there were legal hurdles to their case, with no law on the books specifically about Internet gaming."

With both sides eager for a deal, Giordano agreed to plead guilty to promoting gambling and accept a sentence that would put him in Rikers for about five months. He agreed to forfeit just over $1 million, and waived the right to seek another million seized from other defendants. His 26 co-defendants forfeited more than a million dollars. Some of them also got jail time.

Even though Giordano had already served 10 months in jail, he and his lawyers regarded the plea agreement as something of a victory. He kept his house. He did not have to go to state prison. "The case was a stretch to begin with, but, to use a poker analogy, the decision came down to whether to go all in and force a trial or fold," says Richard Willstatter, Giordano's lawyer in the plea negotiations. "He decided to fold and take a reasonable compromise."

But, if his case was so strong, why, in the end, did he plead guilty?

In an interview shortly before his sentencing, he explained that he was worried he wouldn't get a fair shake in Queens County. "They got a judge to allow them to search computers in a foreign country," he says. "They illegally obtained the information, and a judge upheld them. Am I going to wait to go to trial, lose, appeal, and spend another $100,000-plus? This is the problem I was facing. So I made a reasonable deal. I had put my family through enough."

Queens District Attorney Richard Brown says, "Mr. Giordano was the last of 30 defendants—including his own wife, daughter, and son-in-law—to plead guilty and to admit that they participated in an incredibly lucrative and illegal global gambling operation. . . . Unfortunately for Mr. Giordano, the law enforcement community is just as adept in using new technology to stop him and others involved in such criminal activity."

Giordano's clearly still bitter that he was indicted at all: "The Queens District Attorney is brash and arrogant. It's a little place between Manhattan and Long Island. They need headlines. I was their headline."

Three years of investigations, wiretapping, and another three years of court wrangling to put a bookie in jail for five months: It was a payoff only a sucker would bet on.

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