A movie based on the life of Whitey Bulger?


A story centered on the corruption of the FBI?

Double Check.

Questionable Boston accents?

Oh yeah.

I didn't see The Departed until a few years after it came out in 2006. But just like many others who saw it, I was familiar with the fact that it was loosely based on events involving Whitey Bulger and the infamous Winter Hill gang.

So what's different about Black Mass starring Johnny Depp? There are a few key differences you should be aware of before you write this movie off.


Black Mass centers on the relationship between James Bulger, FBI Agent John Connolly, and Whitey's younger brother Billy. It seeks to detail the deals that were made between Whitey and Connolly, and how the Winter Hill Gang was given a free pass to commit whatever crimes they wanted for years.

The Departed comes close to that. However, Frank Costello (based on Whitey), was not as keen on eliminating his competition (as Whitey in real life was), but more focused on continuing his business opportunities as an (il)legitimate businessman.


One thing you'll immediately notice about Black Mass is that it's a period piece. It looks to take viewers back to the late 1970s and early 80s to when the Winter Hill Gang ran amok in the streets of Boston. It recreates the cars, the clothes, and (unfortunately) the haircuts of that time.

The Departed was actually a remake of a Chinese film, Internal Affairs, and takes place in modern day Boston.

The Ending

I haven't seen the movie yet, but I can guarantee you it won't end with Whitey's death. Whitey is currently serving several life sentences in a Florida prison.

Jack Nicholson's character in The Departed met an untimely demise at the hands of a state trooper he had in his employ. Again, not even close to how Whitey's real life story ended up being.

Looking forward to the film? Come on out with us this Friday night to Flagship Cinemas where we'll be joined by the one and only, Howie Carr. A man who's dedicated most of his career to exposing Whitey, and actually ended up on Whitey's hitlist.

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