The Departed The film takes place in Boston. Irish Mob boss Francis "Frank" Costello plants Colin Sullivan as a mole within the Massachusetts State Police; the two characters are loosely based on famous gangster Whitey Bulger and corrupt FBI agent John Connolly, who grew up with Bulger.Scorsese, Martin. [http://books.google.com/books?id=500THs9cCnMC&pg=PA50 "Martin Scorsese, The Departed" (transcript of 2007 interview)]. In: Kagan, Jeremy. Directors Close Up 2: Interviews with Directors Nominated for Best Film by the Directors Guild of America: 2006 - 2012. Scarecrow Press, 2012. p. 50. Simultaneously, the police assign undercover trooper William "Billy" Costigan to infiltrate Costello's crew. When both sides realize the situation, each man attempts to discover the other's true identity before his own cover is blown.