Critical eye

“Black Mass” the movie: Fact or fiction?

Criminal defense lawyer Rikki Klieman covered the trial of Boston gangster Whitey Bulger as a legal analyst. She looks back on that time and shares how the main players compare with their depictions on film.

Johnny Depp delivers a remarkable portrayal of a chilling, evil, sociopathic killer with a caring side. (Warner Brothers)

Viewing the excellent new film Black Mass, about the notorious and strategic Boston organized crime figure James “Whitey” Bulger, I was riveted to my seat, even though it may have been harder for me than for most audience members to suspend disbelief. I worked as a lawyer in Boston from 1975 to 1994, and covered the Bulger trial as a legal analyst, so I know way too much about the facts and characters in question.

Johnny Depp delivers a remarkable portrayal of a chilling, evil, sociopathic killer with a caring side — a side buried along with Bulger’s mother and his six-year-old son, and obliterated by the LSD trips to which the gangster was subjected as part of a prison experiment. When Depp is on camera, you cannot look away from that dead-eyed stare. He is terrifying.

Yet, by no fault of this fine actor, as I watched the film, I knew that Depp was not James Bulger. Depp had never met him so, as many talented actors do, he created his own version of the man.

Benedict Cumberbatch, in an equally brilliant and nuanced performance, presented his own insightful interpretation of William Bulger, James’ brother, who served for 18 years as president of the Massachusetts Senate. The actor’s version was a bit different from the man I remember. I hate to sound like a jaded Bostonian, but even Cumberbatch’s physical height threw me off: Billy Bulger is much shorter than the actor. However, the brotherly love between Jim and Billy, as presented in the film, rings entirely true.

Rikki Klieman covered the Bulger trial as a legal analyst.

Rikki Klieman covered the Bulger trial as a legal analyst.

Moviegoers unfamiliar with the big story — decades of FBI corruption in connection with the bureau’s organized-crime informants in the gang wars between Italian and Irish mobs — would be well advised to delve into the wealth of informative literature available on the subject. Black Mass, the book, is mesmerizing. In truth, Bulger is only one of many figures in the true story: the stunning corruption of some members of the federal government, which undermined investigations of the State Police and permitted, encouraged and enabled Bulger to rise from a small time hood to a protected organized-crime kingpin, while his brother became one of the most powerful politicians in Massachusetts.

One performance in the film that is uncanny in its accuracy is that of Joel Edgerton as disgraced FBI Agent John Connolly. I knew John well. I worked with him and against him. I went to social functions where he was the life of the party. I even dated a fellow in 1979 who shared a summer house with Connolly, so I saw him in his social splendor. I attended those FBI Christmas parties where he supplied the alcohol. Who knew, then, that he obtained it from Bulger himself?

Edgerton’s performance in Black Mass is beyond Oscar-worthy. It is pitch perfect. He captured Connolly’s speech, his walk — or rather, his strut — his mannerisms and bravado. His final moments on screen show him as an almost exact image of the disgraced Connolly, resigned to his fate, his appearance and demeanor dramatically transformed by his demise. I can’t get Edgerton’s performance out of my head.

Warner Brothers

Johnny Depp as notorious Boston organized crime figure James “Whitey” Bulger. (Warner Brothers)

A striking contrast, and perhaps the least accurate characterization in the film, is that of Stevie “The Rifleman” Flemmi. The script, and not the actor, bears the blame for that. The screen Flemmi, as written, bore no resemblance to the truly despicable criminal that Flemmi is in life. The script makes him out to be a somewhat reluctant follower, a timid, troubled fellow subordinate to Bulger, one who goes along with Bulger‘s corrupt relationship with Connolly. The truth is that Flemmi is a stone cold killer who was an FBI informant for fifteen years before Bulger ever formed an alliance with Connolly. He became Bulger’s partner in crime, not his lackey.

Watching Flemmi testify at the actual trial, I wondered why he got any better deal than Bulger. Then I remembered the rule — he was arrested first and his only chance for a better prison placement, even if he was staying in for life, was to testify against Bulger. Flemmi was nonetheless filled with rage — a heartless killer bearing no resemblance to the softened film version.

None of which means that viewers won’t be gripped by the outstanding performances in this film. They will, and justifiably so.

Rikki Klieman is a legal analyst and an attorney. 


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