The real story of Whitey Bulger and the FBI

Black Mass (2015)

This week was the 10^th anniversary of James “Whitey” Bulger’s sentencing in federal court on numerous murder and drug conspiracy charges.  The anniversary made us think of the remarkable story of Bulger, the FBI, and Massachusetts organized crime. 

This narrative was told as a fictitious “inspired by a true story” movie in The Departed (2006).  If you want a more realistic film about the extraordinary events around Bulger, the movie to watch is Black Mass (2015).

 

Black Mass is a remarkably truthful dramatic look at the corrupt relationship between Whitey Bulger’s Winter Hill Gang and Agent John Connelly of the FBI.  Connelly grew up with Bulger in the Old Harbor Housing Project in Boston.  Connelly became a Special Agent in the FBI and got himself assigned to the Boston Office.  He reunited with Bulger, ostensibly to get information on the Italian Mafia in the city.   

This was the start of a multi-year corrupt relationship with the murderous Irish mobster that allowed numerous killings to occur and made Connelly a quarter of a million dollars in payoffs.  He wasn’t subtle about it either.  He checked most of the box’s indicative of corruption: buying a boat, a condo, a nice house, a flashy watch, tailored suits, and leaving paychecks from the FBI uncashed in his desk.

 

Like The Departed, Black Mass has a fantastic cast.  Whitey Bulger is played by Johnny Depp, who, love him or hate him, is a great actor and gives another gritty performance here.  John Connelly is played by Joel Edgerton who is decent portraying the corrupt and scheming G-Man.  Kevin Bacon (of course), Benedict Cumberbatch, Dakota Johnson, and Jessie Plemons round out the troupe. 

While the movie has some dramatic flair and adds a few minor side plots, it is overall remarkably true to fact for Hollywood.  If you want to learn the nuts and bolts of this story of corruption and murder, you will get them here in this entertaining and dramatic thriller.   Of course, just like in real life, this film has a happy ending as Connelly, Bulger, and Winter Hill mobsters all end up in jail or in the morgue. 

Epilogue: The film was made before Whitey Bulger was murdered under very suspicious circumstances in 2018.  Bulger was transferred to a more dangerous federal prison in West Virginia, where several known mobsters were doing time.  He was moved from a secure unit and placed into general population.  Three men with ties to the Boston Mafia beat him to death while he sat in his wheelchair.

 

 The three perps were identified but for reasons unclear it took the feds four years to obtain an indictment and the trial is not expected to start until the end of 2024.  Perhaps the DOJ doesn’t want another black eye in regard to their dealings with Whitey Bulger.  We are unlikely to get answers until then because, of course, the DOJ can’t comment on “ongoing investigations” (that statement might as well be carved in marble at 950 Pennsylvania Avenue as the DOJ motto).

Black Mass runs about two hours and is both entertaining and informative.  It was interesting enough that I am going to pick up the book it was based on, Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob, by Gerard O’Neill. 

The film can be rented on any streaming service, but we could not find it for free anywhere.  Take a few hours and get an entertaining history lesson with this well-acted true story.  Enjoy!