Despite having won a legal wager in court that allowed him freedom during his final months, Greg Paloian, a well-known bookmaker for the Chicago mob, died June 8 at age 67.
That final bet by Paloian paid off for nearly a year as he managed to stay out of prison to fight a malignant brain tumor.
His attorneys, U.S. prosecutors and a federal judge all pushed his prison report date in consideration of his declining health.
RELATED: Chicago mob bookmaker Greg Paloian wins unusual gamble in federal court after cancer diagnosis
A Facebook picture of the one-time mob bookie showed the usually jovial Paloian seeing dollar signs, which federal investigators long said was a fitting photo for a man who made millions in sports gambling profits for the Outfit.
But, in sentencing him to 30 months last year, a federal judge described Paloian having made a "bargain with the devil" after his previous convictions for similar crimes.
Paloian and his attorneys pushed hard to keep to keep him from spending his last months of life behind bars.
They won that legal bet -- most recently having his prison surrender date delayed to next February -- even though Paloian and his team knew that it was a surrender he probably would never make.
RELATED: Chicago mob bookmaker headed back to federal prison; claims it's a death sentence
He had struck a plea deal with the government in January 2020, admitting to running a large scale sports gambling operation and falsifying his taxes.
According to his guilty plea, Paloian took bets on professional football, basketball, baseball, hockey and college sports.
In the end, U.S. District Judge Joan Lefkow handed Paloian two-and-a-half years in prison, leaving the career bookie to wonder at the time whether it would turn out to be a death sentence for gambling.
The surrender date was put off by Lefkow until the government, Paloian and his attorney, veteran criminal defense lawyer Ralph Mezcyk, could work out an arrangement for the non-violent criminal not to spend his last years of life in prison.
He never served the time and died with the final felony still on his record. A last plea for compassionate release from his sentence was denied on the technicality that he wasn't actually in prison to be released from anything.
ALSO SEE: Whitey Bulger murder: 3 men charged in connection with 2018 death of notorious mobster
Paloian's final bet came at a time when the Outfit has quickly found itself in competition with so many legal wagering sites and opportunities for bettors.
The old-style mob bookie business in which Paloian thrived may be smaller these days, but illegal syndicated gambling with different odds, linked to crime syndicate loan sharks in some cases, is still a money-maker for the Outfit.