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

Becher believes that cases like Giordano's are more about asset seizures than about keeping the public safe.

"For local prosecutors, it's a chance to take down real money," he says. "It's not a deterrent. It's actually an incentive for people to do things the wrong way."

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But Brown sees it as a sort of gateway crime, which justifies his long prosecution of Giordano. "History has taught us that illegal gambling has always been the bread and butter moneymaker for organized crime," he says. "Internet gambling has been compared by some to the crack cocaine epidemic of the late '80s and early '90s. It is highly addictive—it is easy to get hooked. It has been said of Internet gambling that 'You simply click the mouse—and lose your house.' Once you start, you can't stop."

As for the effort to legalize Internet gambling, Frank introduced the latest version of his bill in May 2009. By the end of July, the bill had dozens of co-sponsors in Congress, including Republican Peter King of New York as well as 10 Democratic reps also from this state.

The Frank bill would not allow sports betting, but it appears to allow all other kinds of wagering.

By the time Giordano left for his stint in jail, the bill had garnered 63 co-sponsors.

Meanwhile, the Treasury Department has agreed to postpone enforcement of the Bush Internet gambling law for another six months.

If Frank is successful, the major overseas firms will enter the U.S. market at once, and, more than likely, the big American casino companies will be right behind them.

"The switch is waiting to be flipped," Becher says.

So will Giordano return to the Internet gambling business once he is released from Rikers? No, he says.

"I'm out of it, looking for something else to do," he says.

While his indictment in 2006 was widely covered by the local press, there was only a single reporter at his sentencing last week. His wife and three relatives made up the rest of the gallery.

When his name was called, Giordano, dressed in a gray sweatsuit and fleece jacket, hugged his wife and said, "All right. I love you. Take care of yourself. For now, just put me out of your mind and live your life."

Twenty minutes later, he was escorted from the courtroom through a side door and was on his way to Rikers Island. At the door, he turned one last time to his family.

"Bye, guys," he said.