Then & Now: Revisiting 'Good Will Hunting'
Flynn was a reputed associate of the Winter Hill Gang who had been arrested, but eventually acquitted, in connection with the 1982 murder of Brian Halloran, who was cooperating with the FBI in a case against "Whitey" Bulger.
According to Harrington, Van Sant said, "I'd love to put Jimmy in the movie. He's such a Boston-Irish guy."
Harrington jokingly suggested Flynn play the judge.