Chicago mob bookmaker Greg Paloian wins unusual gamble in federal court after cancer diagnosis

CHICAGO (WLS) -- Outfit bookie Gregory Paloian rolled the dice last January and pleaded guilty to running a large-scale sports gambling operation and falsifying his taxes. But then came a bet with far worse odds: Paloian was diagnosed with terminal brain cancer.

The jovial and longtime mob bookie, whose Facebook photo has him seeing dollar signs, had been sentenced to 2 and a half years behind bars as a result of the plea deal.

Paloian, 66, was supposed to report to the Terre Haute federal prison in Indiana on May 20, 2021. But on May 4, doctors told the court that he suffered two seizures.

Paloian's dire diagnosis was a malignant brain tumor, stage 4, with a very poor prognosis for surviving more than a couple years.

The surrender date was put off by U.S. District Judge Joan Lefkow, until the government, Paloian and his attorney, veteran criminal defense lawyer Ralph Mezcyk, could work out an arrangement for a non-violent criminal not to spend his last years of life in prison.

The I-Team has learned this request from Paloian for compassionate relief has been granted, putting off his prison surrender date for one year. It now stands at August 18, 2022.

Although Paloian is now receiving chemotherapy, the odds of long-term survival, even for a lifelong gambler, are not good. According to the description of his condition in newly-filed court records, and from doctors' statements acknowledged by prosecutors, whether he makes it to that new prison date a year off is not a sure thing, and surviving a 30-month sentence is a long shot.

The past year, numerous imprisoned Chicago Outfit bosses have asked to be released because they feared getting COVID while locked up. Some achieved their freedom, while ohers are still behind bars.

If Paloian makes it to prison, it will be a signal that he somehow survived what doctors are describing as a terminal illness.