Jack Nicholson's real-life inspiration for Frank Costello (the mobster he played in The Departed ) was arrested in Santa Monica, California in June, 2011. James "Whitey" Bulger, a notorious crime boss and former FBI informant for three decades, went into hiding for several years after his deal with the Feds unraveled. The film's plot centers on a Boston police officer (Leonardo DiCaprio) going undercover to arrest Costello. At the same time, Costello's planted an insider (Matt Damon) within the police force for personal gain. Both men are trying to rat out the other. In real life, Damon's character was based on FBI Agent John Connolly, who tipped off Bulger for years to avoid arrest. Billy Costigan, played by DiCaprio is based on a New England State Trooper who joined Bulger's gang. The film's technical advisor, Thomas Duffy, was a former detective assigned to investigate the Bulger's crime syndicate. So if the film feels authentic, it is!
"Whitey" Bulger was ranked in the top ten on the F.B.I's Most Wanted List, and linked to several murders. At the time of his arrest he was found with over $800,000 in cash and 30 guns. The charges against him include racketeering, possession of firearms, conspiracy, and money laundering. Former partners of Bulger have testified that he made payoffs to two dozen Boston police officers and half a dozen F.B.I. agents. John Connolly was convicted for his ties to the crime syndicate, but several other shady characters never faced trial. Despite the fact vs. fiction similarities, The Departed ends much differently than the real-life saga (*Spoiler alert*). Frank Costello meets an untimely end as opposed to Bulger who eluded authorities for almost 16 years. During that time, Bulger reportedly saw a screening of the film.
Since his capture, there's been increased interest in movie location tours in Boston, where some of the filming occurred and Bulger hung out with his mob cronies.
Read more about Bulger's arrest here
Other Boston-area crime sagas:
The Friends of Eddie Coyle