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Bookie balks after judge hands him 30 months in prison

U.S. District Judge Joan Lefkow told Gregory Paloian “you went into this a second time with your eyes wide open and you made a bargain with the devil that it would work out.” But because of Paloian’s medical issues, she stopped short of a stiffer sentence prosecutors had sought.

Dirksen Federal Courthouse
Sun-Times File

Before she sentenced a man who had admitted running an illegal sports gambling operation in which people allegedly lost tens of thousands of dollars, a federal judge noted Wednesday it wasn’t the first time the man had gotten in trouble for gambling.

Rather, U.S. District Judge Joan Lefkow told Gregory Paloian, 66, “you went into this a second time with your eyes wide open and you made a bargain with the devil that it would work out.” Still, because of Paloian’s medical issues, Lefkow stopped short of a stiffer sentence prosecutors had sought, handing Paloian two-and-a-half years in prison instead.

“Your honor,” Paloian said, clearly disappointed. “Thirty months in the penitentiary?”

A heavy sigh came next. Then, during what seemed more like a casual back-and-forth than a formal federal court sentencing, Paloian and his attorney tried to bargain and quibble with the judge. And a prosecutor eventually joined in during the hearing held by video.

Defense attorney Joseph Urgo asked whether part of the sentence could be served in home confinement. Paloian said Lefkow’s ruling could turn out to be a death sentence. He admitted he made mistakes. But he asked, “What does this sentence accomplish other than the ultimate kick-somebody-when-they’re-down?”

Assistant U.S. Attorney Terry Kinney then countered that Lefkow should revoke credit given to Paloian for accepting responsibility for his crime — a move that could increase Paloian’s sentence. Kinney insisted that Paloian “has no touch with reality.”

But Lefkow finally ended the argument, telling both sides, “I am not persuaded to change my sentence either way.” And she told Paloian a 30-month sentence is reasonable.

“I know that it’s a hard pill to swallow,” Lefkow said.

Kinney asked last week for closer to three years for Paloian, a man with purported mob ties who pleaded guilty in January to running an illegal sports gambling operation. The prosecutor pointed to Paloian’s criminal history, which included a racketeering conviction involving a large gambling enterprise that ran from 1985 until 1998.

But Kinney also said Paloian and his agents in the latest gambling ring hounded gamblers as they lost tens of thousands of dollars, even prompting one gambler who couldn’t pay his debts to “burst into tears.” Kinney has said the ring included 60 gamblers, and one of the “most prolific agents” was “a veteran police officer from a local police department.”

Kinney has also tied Paloian’s case to another gambling case involving Vincent “Uncle Mick” DelGiudice.

Paloian and his agents referred to their gamblers as “goof, goofball, idiot, ‘f*&#%g little pu$%y’, little c&%*sucker and other descriptive monikers,” Kinney wrote in a court memo. Paloian also allegedly referred to one gambler as “an annuity,” a “dumb f#%k” and “an idiot and he pays.”

Urgo insisted in his own court memo that prosecutors had not found one example where a “customer” or “agent” of Paloian’s gambling ring suffered financial hardship or exhibited signs of problematic gambling habits — a claim Kinney challenged. Urgo also wrote that FBI agents confronted Paloian about their investigation into his gambling ring on Dec. 9, 2019, at a Starbucks in Melrose Park.

Paloian “immediately made very excellent decisions and has continued to make excellent decisions ever since those first moments in Starbucks,” Urgo wrote.

Before Lefkow handed down her sentence Wednesday, Paloian admitted what he did was wrong, and he insisted he “would never, ever, ever book again.”

“I am a criminal,” he said. “I admit it. I broke the law.”