‘Black Mass’ Reveals Dark Life of Boston Gangster Whitey Bulger


In Boston there was a time when the Winter Hill Gang reigned supreme. The story on how they ruled the Boston underworld is a familiar story locally, and its one that has captivated the minds of everyone in Boston for years. Now the story is going worldwide as Johnny Depp plays Whitey Bulger in the Warner Brothers movie ‘Black Mass,’ a story that has long since become engrained in Boston’s urban legends of the rough South Side of the city.

Operating with impunity as a the ring leader of a ruthless empire that moved drugs, buried bodies, gambled, extorted through violence, and other means, Irish Mafia boss Whitey Bulger was as cold as the New England winters. At this point, knowing rappers, we wouldn’t be surprised if  his name is in the works to become the title of a Boston rapper’s mixtape if it hasn’t already.  With a rap sheet that included a stint at Alcatraz and over 19 murders Bulger got it done with the law on his side, having a brother that was deep in the political game of Massachusetts.

But in this true story crime drama, there are twists and turns that leave a blemish on Whitey’s career as a gangster. Having struck a deal with Boston’s division of the FBI, Whitey was able to run the South side of Boston while he operated as an informant for the ABC boys. Did you say snitch or rat? To Whitey it wasn’t being a rat, it was a business decision that allowed him to make millions moving drugs and dominating the lucrative black market of Boston’s underworld.

Although Jim Bulger still maintains to this day that he “never cracked,” FBI sources say that he simply doesn’t want it to be true given his “Southie” upbringing that frowned upon rats.  Either way corruption was rampant. At times Whitey says he paid FBI employees as much as $25,000 – $50,000 cash handing them a box or envelope. To the Winter Hill Gang there was always a way to corrupt government agents. While the FBI was focused on the Italian Mobb, they let the Godfather of the Irish Mafia do his dirty work with no repercussions. To this day Bulger maintains that he always asked the questions, him running the convos and looking for tips, not the other way around.

Hip-Hop culture has always had a fascination with gangsters like Scarface, Goodfellas and other crime movies – this one def adds to the list of films for us to enjoy . Johnny Depp is ruthless, dark and at times chillingly comfortable in his role as a sick and twisted Boston mobster that killed over 19 people that we know about.

While the film tells an incredible story of how the law can get tied up in the streets, but the truth of the matter is that many people lost lives and this guy tormented South Boston for decades. How did the Boston FBI really allow this to happen? The answer and eventual scapegoat was John Connelly, who finds himself at the center of this film. We won’t ruin for you but this is def a good gangster movie for anyone looking to know more about Whitey Bulger the notorious Boston gangster.