Eponymous Gangster Week Continues: How Much Whitey is in The Departed?

Seen from a distance and when studied in minute detail, The Departed synchs up closely with Whitey Bulger. But in mid-range, they have nothing to do with each other.

Pull back as far as you can, and The Departed is the story of a powerful Boston mob boss with close ties to corrupt law enforcement agents. That’s obviously a story very much in line with Whitey’s life.

Get a little closer and things diverge dramatically. Like how Billy Bulger’s not in the movie. You’d think a movie so thematically invested in duality and the line between crime and crime fighting could make room for a corrupt politician brother. But that character is outside of the plot mechanics of Infernal Affairs. 

Also, because the movie follows the Infernal Affairs template as closely as it does, law enforcement gets off easy. According to multiple accounts, it wasn’t just a lone bad cop working with Whitey; the whole Boston FBI office was under Whitey’s sway. All the business about Matt Damon surreptitiously communicating with Jack Nicholson was fiction: Whitey’s real life FBI buddy Zip Connolly used to just leave his front door open so Whitey could make nighttime visits.

But more importantly, aside from being an enthusiastic murderer, Nicholson isn’t playing a character that’s much anything like Whitey. Nicholson’s a hard-living, bloated badass. IRL, Whitey is a teetotaling fitness nut. And while Whitey is evidently keenly interested in World War II, he’s hardly the James Joyce-quoting erudite Nicholson plays.

So OK, then, the screenwriters didn’t want to model the character too closely on Whitey or the Winter Hill gang. Except then either by accident or little dog whistle peeps, they left in a lot of weird parallels to Whitey’s life.

  • Kid Matt Damon is seduced by Jack Nicholson with milk and groceries. Whitey bought Zip Connolly ice cream as a kid.
  • Kid Matt Damon conspires with Whitey at an auto-repair garage. Whitey’s Winter Hill gang used to meet at an auto garage.
  • The movie opens with scenes from ’70s Boston racial riots, which while irrelevant to the film’s story, were hugely important to the rises of both Bulger brothers.
It could never happen, but it would be interesting to make a more accurate Whitey biopic and have the exact same cast. Damon and Di Caprio could play young Billy and Whitey and Martin Sheen and Nicholson could be the old versions and you could flash back between the two, Godfather II-style.
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