Before she sentenced a man who had admitted running an illegal sports gambling operation in which people allegedly lost tens of thousands of dollars, a federal judge noted Wednesday it wasn’t the first time the man had gotten in trouble for gambling.

Rather, U.S. District Judge Joan Lefkow told Gregory Paloian, 66, “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.” Still, because of Paloian’s medical issues, Lefkow stopped short of a stiffer sentence prosecutors had sought, handing Paloian two-and-a-half years in prison instead.

“Your honor,” Paloian said, clearly disappointed. “Thirty months in the penitentiary?”