The true story behind Jack Nicholson’s character in ‘The Departed’
As well as being a remake of 2002 Hong Kong crime classic Infernal Affairs, Martin Scorsese’s The Departed also took several cues from real-life criminal cases to flesh out its complex web of double-crosses, undercover informants, and citywide corruption.
Even though Scorsese drew the line at the studio’s desire to have his own labyrinthine tale emulate Infernal Affairs by spawning multiple sequels, everybody was evidently happy with the end result based on its Academy Award wins for ‘Best Picture’, ‘Best Adapted Screenplay’, and ‘Best Editing’, even if the biggest cheers were reserved for the legendary filmmaker finally taking home that ‘Best Director’ trophy.
In addition to liberally lifting story elements and plot points from Infernal Affairs, The Departed was indebted to a pair of criminal figures above all others. Matt Damon’s Colin Sullivan was based in part on the corrupt FBI agent John Connolly, with Jack Nicholson’s Frank Costello sharing several traits with notorious kingpin Whitey Bulger.
Ironically, given the close relationship shared between Sullivan and Costello in the film, Connolly was Bulger’s handler during the latter’s time as an FBI informant, another characteristic that was applied to Nicholson’s fearsome criminal figurehead. Although their shared history isn’t exactly recreated beat-for-beat, Bulger was nonetheless left seriously displeased at the way he was broadly recreated on-screen.
Casey Sherman – co-author of the book Hunting Whitey: The Inside Story of the Capture & Killing of America’s Most Wanted Crime Boss – told The Hollywood Reporter that Bulger was left seething when he saw The Departed. As well as the revelation that “the first time that Whitey jeopardised his own freedom” during his time on the run from the authorities was to go and see the movie, he was caught by a Sheriff’s deputy showcasing his disapproval at the three-time Oscar-winning icon’s work.
As Sharman explained, the deputy told them in an interview “that Bulger shook his head in disgust many times while watching Jack Nicholson’s fictional version of him on the big screen”. Of course, Bulger spent years denying that he’d informed the FBI on criminal activity in Boston despite the fact he’d most definitely been feeding them information, whereas Costello is only outed as a rat towards the end of The Departed when his illicit house of cards begins tumbling down.
Bulger wasn’t convinced by Johnny Depp’s turn in the biopic Black Mass, either, and he refused to cooperate with the production “because Depp’s character gave away secrets to the FBI and ratted out both his friends and gangland rivals”. Even when he’d become a renewed source of intrigue and fascination, he still wouldn’t come clean on his double life as a federal asset.
Costello being outed as an informant adds another layer to the intrigue at the heart of The Departed, but as far as the character’s inspiration goes, they both share the sentiment of having no acknowledgement of their irrefutable status as a rat.
