Chicago Bookmaker With Mob Ties Gets 30-Month Prison Term for Illegal Sports Betting Operation

  • Gregory Paloian ran a sports betting operation in Chicago for four years starting in 2015
  • Prosecutors said the business generated “hundreds of thousands of dollars” for the 66-year-old
  • Judge Lefkow noted the offender’s previous gambling convictions, including ties to the mob
  • The defense argued that the term constituted a death sentence, but Lefkow affirmed her ruling
Prisoner being led away by guard
In Chicago, 66-year-old bookmaker Gregory Paloian has received a 30-month prison sentence for operating an illegal sports betting business for four years. [Image:]

A profitable illegal enterprise

A Chicago bookmaker with ties to organized crime has received a two-and-a-half-year prison sentence for illegal sports betting and tax offenses.

According to a Wednesday release on the Department of Justice (DOJ) website, Gregory Emmett Paloian conducted his illegal bookmaking business in Chicago, Melrose Park, and Elmwood Park. The 66-year-old began the operation in 2015 and accepted wagers on a range of sports for four years, including collegiate games.

Paloian pleaded guilty to one count of running an illegal gambling business, and one count of filing a false tax return

Earlier this year, Paloian pleaded guilty to one count of running an illegal gambling businesss, and one count of filing a false tax return. US District Judge Joan Humphrey Lefkow handed down the 30-month sentence after a hearing in Chicago on Wednesday.

In the sentencing memorandum, assistant US attorneys Terry Kinney and Ankur Srivastava described Paloian’s enterprise as a “highly lucrative illegal business.” They said the offender and his agents generated “hundreds of thousands of dollars” by taking the sports wagers.

Paloian’s previous offenses

Paloian’s sentencing brings the case to a close following the pressing of charges and subsequent arraignment in October last year. Judge Lefkow noted Paloian’s previous gambling transgressions when delivering her verdict on Wednesday. As reported by the Chicago Sun Times, she told the defendant:

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.”

Lefkow was referring to offenses that saw Paloian arrested multiple times over the past 20 years. His criminal record includes a 1980 conviction on charges of extending juice loans to gamblers. Chicago police also arrested Paloian in 1995 for taking wagers at a basketball facility in Elmwood Park.

Most notably, a federal judge sentenced the bookmaker to three-and-a-half years in prison in 2002 for running a sports betting operation in collaboration with the Chicago mob. Under the protection of West Side Outfit boss Rocky Infelise, the enterprise ran for more than two decades between 1985 and 1998, taking in millions of dollars in the process.

In addition to his gambling-related charges, part of Paloian’s sentencing related to tax offenses. The bookmaker filed false tax returns between 2012 and 2018 to under-declare his income. According to the DOJ release, this cost the IRS $172,458 and the Illinois Department of Revenue $25,238.

A possible death sentence

Last week, assistant US attorney Terry Kinney initially requested a three-year sentence for Paloian. In addition to the defendant’s criminal past, Kinney pointed to the tens of thousands of dollars lost by gamblers and the disregard shown towards his customers.

the ultimate kick-somebody-when-they’re-down”

Although the judge ultimately served a shorter sentence than Kinney hoped for, defense attorney Joseph Urgo still raised issue with its length. He argued that, owing to Paloian’s poor health, the 30-month term essentially constituted a death sentence. He asked: “What does this sentence accomplish other than the ultimate kick-somebody-when-they’re-down?”

Lefkow refused to change the sentencing, even though she said the defendant might find it “a bitter pill to swallow.” Meanwhile, in his concluding statement, Paloian ultimately admitted to wrongdoing and insisted he “would never, ever, ever book again.”

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