Cancer-Diagnosed Mob Bookie Greg Paloian Plays Compassionate Relief Card, Wins Year’s Prison Reprieve

  • A federal court has granted Paloian’s request for compassionate relief due to cancer
  • Paloian had to surrender himself to Terre Haute federal prison in Indiana on May 20, 2021
  • Terre Haute prison now expects Paloian to begin his sentence on August 18, 2022
  • Paloian’s mob connections included Rocky Infelise and the feared enforcer Jimmy Inendino
  • The former Outfit bookie finally confessed, insisting he’d “never, ever, ever book again”
Bird escaping cage
Former Outfit bookie Greg Paloian has been given a year’s reprieve on prison after a federal court granted his request for compassionate relief based on a cancer diagnosis. [Image: Shutterstock.com]

Paloian ran book for Chicago mob

If you’ve run a book for the Chicago mob, you probably get wise early to having a get-out-of-jail-free card up your sleeve for contingencies. Outfit bookmaker Gregory Paloian, 66, had one such card, which he recently used to literally get out of jail.

According to a report by ABC7 Chicago’s I-Team on August 6, Paloian won a year’s delay on his prison term after a federal court granted his request for compassionate relief based on an aggressive cancer diagnosis.

The I-Team’s Chuck Goudie took to Twitter in April to publicize a news report on Paloian’s 30-month prison sentence, accompanied by a Facebook photo of the bookie wearing dollar-sign novelty specs.

US District Judge Joan Lefkow sentenced Paloian to two and half years behind bars on April 7, 2021 as a result of a plea deal.

At that time, reported the Chicago news station, Paloian begged Judge Lefkow “for mercy in the form of probation,” informing the court that doctors had diagnosed him with early onset Alzheimer’s. According to news reports, Paloian’s sentence was “on the low end” of what federal prosecutors wanted.

Doctors subsequently diagnosed Paloian with a malignant, stage 4 brain tumor.

Under terms of the April sentence, Paloian had to surrender himself to Terre Haute federal prison in Indiana on May 20, 2021. On May 4, however, doctors informed the court the ex-mob bookie had suffered two seizures. Doctors subsequently diagnosed Paloian with a malignant, stage 4 brain tumor.

After the court granted his appeal for compassionate relief, Terre Haute now only expects to welcome Paloian on August 18, 2022.

Long odds for lifelong gambler

While Paloian is now undergoing chemotherapy treatments, the odds of surviving the type of cancer doctors’ diagnosed him with are long, at around the two-year mark.

According to the I-Team’s report — citing a description of Paloian’s condition from freshly filed court records and from “doctors’ statements acknowledged by prosecutors” — whether the lifelong gambler makes it to Terre Haute in a year, let alone survives a 30-month stretch, is “a long shot.”

vigorously pressing hi-stakes losers to pay up, with the threat of the Outfit always present”

In January 2021, Paloian struck a plea deal with the government, confessing to falsifying his taxes and running an extensive illegal sports betting operation for over four years, taking bets on pro football, baseball, basketball, hockey, and college sports. According to news reports in April, prosecutors say the bookie raked in “hundreds of thousands of dollars in an average month handling bets and vigorously pressing hi-stakes losers to pay up, with the threat of the Outfit always present.”

During his 45-minute telephone hearing in January, Judge Lefkow asked Paloian to say in his own words what his wrongdoings were. Answering in an unemotional tone, the outfit bookmaker said: “I took sports wagers from various friends of mine and people that I knew, and paid or collected depending on the outcome of the games.”

Court records show Paloian’s checkered criminal history includes Chicago Outfit connections and friendships with notorious underworld characters including John “Quarters” Boyle, West Side Outfit boss Rocky Infelise, and feared mob enforcer Jimmy Inendino.

Chances of surviving prison?

If Paloian gets to prison, serves his term, and walks free, it might not come as a surprise given his instinct for self-preservation. According to the Chicago Tribune, Chicago police caught Paloian jotting down suspected bets at an Elmwood Park basketball facility in 1995.

When police approached him, Paloian stuck bunches of paper in his mouth and “fell to the ground and rolled around” until he had swallowed them, prosecutors said.

In Paloian’s concluding statement after his April sentencing, however, the former Outfit bookie finally owned up to doing wrong, insisting he’d “never, ever, ever book again.”