What’s It AboutThe true story of Whitey Bulger, the brother of a state senator and the most infamous violent criminal in the history of South Boston, who became an FBI informant to take down a Mafia family invading his turf.

“Most of What Follows is True” is how my favorite movie, Butch Cassidy & The Sundance Kid, opens.  If Black Mass opened the same way, it would be entirely too fitting as Whitey Bulger is the closest thing to an outlaw modern America has ever seen.  

I’ve lived in Massachusetts for the overwhelming majority of my life.  Growing up in the 80’s and 90’s in Massachusetts there were things that you learned and things you just knew.  

What you Knew

  • As long as Larry Bird was in the building, the Celtics had a chance to win
  • There are four seasons, but in Boston you only get two: Winter and humidity
  • The name Whitey Bulger


Things You Learned

  • The Red Sox would always lose but you had to love them more for it
  • A Bubbler is a water fountain, a frappe is a milkshake, a rotary is a traffic circle
  • The name Whitey Bulger


Weird, right?  How do you both “know” and “learn” something?  Let me explain.

You “knew” the name Whitey Bulger carried weight; you “learned” why you should fear it.  South Boston is not a huge town — 35,000 people live there.  At least triple that claim to have known or been influenced by the most notorious gangster in modern history.  You can’t throw a rock in greater Boston without pegging someone who has at least one Whitey story.  Some people tell stories about high school glory days, some people tell stories about vacations.  If you meet someone between 45 and 70 and they are from the stretch of Massachusetts from Braintree to Medford, they most likely tell at least one story that begins with, “Oh yea… I knew Whitey.  One time I saw Whitey do X,” with X being any number of horrifying things.



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The Whitey tales are rarely told as good news, despite the grinning teeth telling them.  Anecdotal cautionary tales told like war stories.  Remembrances of what Boston used to be like back in the “good” old days.   

The grip he had on an entire generation of Bostonians is astounding.  When talk radio host and frequent Bulger basher, Howie Carr, released his book, The Brothers Bulger, I went to the book signing in Braintree, MA.  The crowd that showed up was there for one reason– to heckle a journalist who dared speak ill of a folk hero.  “Sure, Whitey did ALL the crime for twenty-five years, but he was OUR GUY!  He bought me a bike once!”  Things like that.  It was bizarre.  

Remember the scene in Spider-Man II when Spidey saves a train load of people and loses his mask in the process?  The crowd of people all see his naked face and when Spider-Man realizes they have, a child hands him back his mask and says, “don’t worry… I won’t tell.”  The citizens of that fictional New York banded together to protect the secret of their hero.  That was the “neighborhood” approach to Whitey.  Bulger survived at large for so many years because of the protection he received from the masses.  It was as if everyone turned their heads and didn’t see nothin’ because he did the dirt, but he didn’t do it to “us.”  

To hear some people speak of him, he was Robin Hood and the Winter Hill Gang was his band of Merry Men.  To others, he was the Boogie Man.  The legend of Whitey lurking behind every corner and as ever present as a shadow.  A man whose exploits could serve as a bedtime cautionary tale to the youth of Boston.  

“Don’t break the rules… or Whitey will get you.”


Any great fictional crime story centered in Boston has a hint of Whitey to it.  It would be impossible not to.  He is as synonymous with the romanticized gritty version of Boston as a dropped R.  From Dennis Lehane’s series of books to movies like The Departed, The Town, and Mystic River, the gangster rising up from the streets in fiction would be doing so in the shadow of James Bulger.  

In the same way that ghost stories are told when the audience feel like it’s safe, it is only fitting that now with Whitey behind bars that a biopic based on his life would be released.  Black Mass is a biopic as it’s main subject is a real person and the stories weaved together to make this film are mostly real.  What I’m choosing to view this movie as is a fairytale, but one of Grimm’s Fairytale– the source material that has given us so many happy-ending-blue-skies Disney movies.  This is a fairytale that is centered around the monster who also happens to be the hero.  Which stereotype Whitey fills depends on which side of Boston you’re from.  All that is missing is a poisoned apple or a spinning wheel.  

While the Butch & Sundance quote sums up the movie and the liberties taken to make a compelling film, the most apropos quote to describe the story comes another film of star Johnny Depp.

“You best start believin’ in ghost stories… You’re in one.”


Cinemadness Pre-Cap Gut Reaction: Black Mass is going to be great.  It could be the hometown effect, but I doubt it.  There’s no way this many amazing actors could attach themselves to a subpar product.  This should be everything we loved about Goodfellas and The Departed and everything we came to appreciate about Gone Baby Gone rolled into one.

When Should You See It: Opening Night

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