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Feds want stiff prison sentence for bookie in gambling case, say he tried to sell judge a ‘fantasy’

A series of court records open the widest window yet into the gambling case involving Gregory Paloian.

Dirksen Federal Courthouse
Sun-Times file

Federal prosecutors are asking a judge to hand a stiff prison sentence to a bookie with purported mob ties, insisting he tried to sell a “fantasy” to the judge about a fun and fair gambling ring that, while illegal, aimed never to exploit anyone.

In reality, Assistant U.S. Attorney Terry Kinney wrote in a court filing Wednesday that Gregory Paloian and his agents hounded gamblers for payments as they lost tens of thousands of dollars, and even prompted one gambler who couldn’t pay his debts to “burst into tears.”

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

Paloian defense attorney Joseph Urgo last week asked U.S. District Judge Joan Lefkow to spare Paloian from prison. Urgo wrote 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.

He wrote in a court memo that Paloian “conducted that business in as ‘clean’ a manner as possible, the goal being to never financially exploit anyone, never allow anyone to gamble beyond their means. And safeguards were developed and utilized to ensure this.”

But Kinney, in his own memo Wednesday, wrote that Urgo’s memo was “more fantasy, tall tales, and wishful thinking than reality.” The prosecutor asked Lefkow to give Paloian a prison sentence at the higher end of a range laid out by federal sentencing guidelines. Paloian’s plea agreement estimated that would be around three years, but prosecutors may challenge that.

Kinney also made note of Paloian’s criminal history, which included a racketeering conviction involving a large gambling enterprise that ran from 1985 until 1998.

The court records, along with recently unsealed search warrant affidavits, open the widest window yet into the case against Paloian, who was first charged last October. When Paloian pleaded guilty in January to running an illegal sports gambling operation, Kinney hinted at wide-ranging evidence that included “a large number” of recordings.

The following month, Kinney tied Paloian’s case to another gambling case involving Vincent “Uncle Mick” DelGiudice, who has admitted running a sports bookmaking business from 2016 to 2019 around Chicago. That case also led to charges against Mettawa Mayor Casey Urlacher, the brother of Chicago Bears great Brian Urlacher who was pardoned in January by Donald Trump in the final hours of Trump’s presidency.

Urgo wrote that FBI agents confronted Paloian about their investigation into his gambling ring on Dec. 9, 2019, at a Starbucks in Melrose Park. Urgo wrote that Paloian “immediately made very excellent decisions and has continued to make excellent decisions ever since those first moments in Starbucks.” He also wrote that Paloian “immediately unlocked his smartphone so the agents could have easy access, and he then surrendered the phone.”

One of those agents wrote in an affidavit seeking a search warrant in March 2020 that agents immediately put Paloian’s phone in “airplane mode” after seizing it so it could not be remotely accessed. Even though the phone initially appeared to contain relevant text messages, “a subsequent review of the phone several days later revealed that its data had been erased,” the agent wrote.

Urgo declined to comment on the case Thursday morning.

In a related affidavit filed in December 2019, the agent wrote that law enforcement sought to tap Paloian’s phone Feb. 27, 2019, and conducted physical surveillance of Paloian and another individual March 15, 2019, as they visited The Dome at the Parkway Bank Sports Complex in Des Plaines.

Kinney wrote that authorities “know now that Paloian was running a bookmaking operation as early as 2012 and continuing until shut down by the FBI.” He wrote that the ring included 60 gamblers and wrote that “one of his most prolific agents” was “a veteran police officer from a local police department.”