Chicago Bookie With Mob Ties Faces Illegal Sports Betting Business Charges

  • 66-year-old Gregory Paloian ran this latest operation for four years, starting in 2015
  • Federal authorities want him to forfeit $274,070 and a 2017 Audi
  • The single charge carries a maximum federal prison sentence of five years
  • Paloian was sentenced to three and a half years in prison in 2002 for running another operation
Man fanning out stack of money
66-year-old Gregory Paloian, a Chicago bookie with mob ties, is facing federal charges for operating an illegal bookmaking business. [Image: Shutterstock.com]

Latest conviction

A 66-year-old bookmaker with ties to organized crime is facing charges once again for allegedly operating an illegal sports betting business in the Chicago area.

Gregory Emmet Paloian allegedly ran the gambling operation for four years, beginning in 2015. It was based mainly in Chicago, Elmwood Park, and Melrose Park as per the two-page document filed in Chicago on Friday.

 faces a single count of conducting an illegal gambling business

Federal authorities are looking for Paloian to forfeit $274,070, as well as a 2017 Audi. He faces a single count of conducting an illegal gambling business, which carries a maximum federal prison sentence of five years. The arraignment is set to take place on October 7 in Chicago in front of US District Judge Joan Humphrey Lefkow.

While the defendant’s attorney did not comment on the case, defendants who are charged via criminal information usually plan to plead guilty, according to the Chicago Tribune.

Mob links

Before this latest bookmaking operation, Paloian was sentenced in 2002 to three and a half years in prison for operating what was called a “hugely successful” bookmaking operation that had links to the mob.

It ran for more than two decades, taking in millions of dollars. During his sentencing hearing in 2004, Paloian said: “If I didn’t book, I wouldn’t be here.”

This betting ring was said to be under the protection of West Side Outfit boss Rocky Infelise. If customers were not paying their debts, Paloian said that he would make threats of referring them to get juice loans from the feared mob enforcer Jimmy Inendino.

A sentencing memo in 2002 from prosecutors detailed: “Paloian said that a bettor would be told cannons would be pointed at his head if he didn’t pay.”

Origins of his bookmaking

Paloian began bookmaking in the late 1970s when he was accepting bets in Riis Park, located on the West Side. Eventually, he started to accept bets over the phone while on the move. 

Once, after he was confronted by police, Paloian allegedly swallowed betting paper in an attempt to get rid of evidence. Over the years, he has been arrested dozens of times.

During a raid on his house in 1998, police found $150,000 in cash, as well as diamonds, Krugerrands, and jewelry. Most of the items were in safes hidden in a secure room that was discovered behind a fake wall in the basement. Also found was soluble paper, commonly used by bookies for recording bets, as well as a voice-changing device.