Black Mass: The story of Whitey Bulger, gangster and FBI informant

Directed by Scott Cooper; written by Mark Mallouk and Jez Butterworth; based on the book by Dick Lehr and Gerard O’Neill

Black Mass, with Johnny Depp, is based on the career of the notorious Boston crime boss James “Whitey” Bulger, one of the FBI’s Ten Most Wanted Fugitives from 1999 until his capture in June 2011. After Osama bin Laden, number one on the list, was killed by US forces in May 2011, Bulger was briefly moved to the top. The FBI offered $2 million for tips leading to his arrest, the largest sum ever offered for a US fugitive.

Throughout the 1970s and 1980s, Whitey Bulger was the head of the Irish mob crew known as the Winter Hill Gang, which largely controlled Boston’s underworld. His brother, William “Billy” Bulger, was President of the Massachusetts Senate from 1978 to 1996. After his 2011 arrest Whitey Bulger was charged with 19 counts of murder, racketeering, money laundering, extortion and weapons smuggling. He is in prison today.

Although the extent of Bulger’s relations with law enforcement is not entirely clear, it is well-documented that he began cooperating with the FBI in 1975 to provide information on the Italian mafia. Whitey had connections within the Boston Police Department, the Massachusetts State Police and the FBI, all of whom aided his reign of crime and violence. Bulger also gave money and guns to the Irish Republican Army (IRA), which was fighting British occupation of Northern Ireland during the time.

Much of the money his gang made was from shakedowns of other drug kingpins in the Boston area. Eventually, by the mid-1990s, Bulger fell out of favor with his FBI handlers and was forced to go on the run for the next 16 years. When he was captured in a Santa Monica, California apartment in 2011 it was feared he would name names in his trial.

The FBI, in particular, had reason to worry. In exchange for Bulger’s information against the Italian mafia, the FBI shielded Bulger and his friends from prosecution. Wiretaps were exposed, as were government agents within Bulger’s gang who were then murdered by Bulger. Innocent people were framed for murders committed by Bulger’s gang, and left to die in prison. Much of this is now known because of civil lawsuits brought against the federal government by the family members of Bulger’s victims.

Given this lurid yet revealing history of organized crime in Boston, it was somewhat inevitable that Hollywood would turn its glamorizing sights on this story of police and thieves. In fact, Jack Nicholson’s mob boss character in The Departed by Martin Scorsese (2006), a deplorable film, was loosely based on Whitey Bulger.

American director Scott Cooper, whose credits include Crazy Heart and Out of the Furnace has now made Black Mass starring Depp as Bulger. Benedict Cumberbatch plays Senator Billy Bulger, Joel Edgerton plays FBI agent John Connolly, who recruited Whitey as an informant, and Jesse Plemons plays Kevin Weeks, Whitey’s right hand man and “enforcer.”

The film is competently made. There are strong performances throughout, especially from Depp who is almost unrecognizable underneath heavy makeup. The music and cinematography is quite effective and one gets the sense that the filmmakers tried to be as historically accurate as possible in recreating the physical look and feel of Boston in the 1970s and 1980s, when much of the story takes place.

Having said that, Black Mass curiously fails to bring this complicated history to life and the final result is an unsatisfying picture, dramatically and aesthetically. The film is not as violent as the typical Scorsese or Quentin Tarantino effort, but there is too much of a (lazy) focus on the beatings, shootings and strangulations that Bulger and his men commit. It is also difficult to determine what exactly director Scott Cooper is trying to say about this “unholy” nexus between the cops and robbers.

Both the relationship between Bulger and his brother, one of the leading Democratic Party politicians in Massachusetts at the time, and between Bulger and the FBI are deeply suggestive. Would Whitey Bulger have known the success he did without these connections? What does this say about the nature of “crime” and “justice” in class-divided America? Moreover, the timeframe of the movie is significant: the mid-1970s to the mid-1990s, the age of Reagan, Bush and Clinton, the worship of the “free market,” greed and individualism, the collapse of the Soviet Union and the “end of history,” etc. None of this is given much attention.

Certain elements of Black Mass are quite effective. The corruption of the police and the politicians in particular rings true. There is almost a seamless continuity between the smoky and dim-lit bars that Whitey and his men drink in and the elegant restaurants and sterile offices of the police and public officials. A division of labor, so to speak, exists. The FBI and the police, along with the politicians, preach “law and order” in public, while, in reality, they collaborate with and make use of powerful thugs like Whitey Bulger.

At one point in the film, FBI Agent John Connolly (Edgerton), who helps tip off Bulger about the agents and informants in his midst, is seen driving a flashy car and wearing a pin-stripe suit, with sunglasses and jewelry, all of course paid for by Bulger’s bribes. It is difficult to tell where the gangster ends and police official begins. This obviously is the point.

However, the character and contradictions of working class life in Boston are not deeply explored, including the question of “snitching” and the city’s so-called code of silence. Thugs like Bulger took advantage of the tight-knit and besieged South Boston working class to enrich themselves. Under conditions where the political officialdom was discredited and despised, the Irish mob presented itself to the impoverished community at times as an alternative social authority, gaining credibility as well for its running guns for the Irish Republicans. This was of course entirely a fraud, as both Bulger’s anti-social violence and his collaboration with the FBI and police should indicate. Black Mass is not clear about these issues.

Indeed, the film is somewhat ambiguous toward the figure of Bulger himself. He is a sociopath to be sure, but also a loving father and devoted son to his ailing mother. A number of the scenes, such as the one where Bulger scolds one of his agent-handlers for “spilling” the family recipe over the dinner table, have a tired quality to them. We have seen this sort of sequence in Scorsese’s Goodfellas and numerous other movies.

By the end, Black Mass becomes somewhat tedious. It is not the most memorable entry in the crime genre in recent years.

As a historical note, 2015 is also the 40th anniversary of the Boston school desegregation crisis. In 1974 US District Court Judge W. Arthur Garrity Jr. set out a plan for compulsory busing between predominantly white and black schools, which ignited protests in white neighborhoods. In the face of opposition to the plan, the police essentially occupied South Boston in 1975 and various “left” elements declared the problem to be the wholesale racism of the white working class and called for federal troops to be sent in.

Every effort was made to divide the working class in Boston and whip up backwardness. To provide some sort of social context, during the desegregation crisis, while white students citywide received more funding per student than black students, students at predominantly white (and poor) South Boston High School received less than students in majority black schools in Roxbury.

The Workers League, predecessor of the Socialist Equality Party, opposed both the racist elements and the middle class “left,” which tied itself even more firmly to sections of the Democratic Party and its allies such as the NAACP. The Workers League campaigned for the unity of the working class in the fight against poverty and racism.

Whitey Bulger, unsurprisingly, was violently opposed to de-segregation, and rose to prominence during those years. An associate of Bulger’s, James Kelly, headed the South Boston Information Center, the leading anti-busing group.

In a perceptive essay, “Busing & Whitey Bulger,” written to commemorate the anniversary for WGBH News, writer Michael Patrick MacDonald reminisced:

“In my neighborhood, we always knew there were two Southies [nickname for South Boston]—and that while some people in Southie ‘knew people,’ most of us had absolutely no connection to power. … Our chants of Hell No We Won’t Go [in opposition to the busing plan] rose up in unison from the grimy projects to the vinyl-sided row houses of the West Side to the hills of City Point. And united we jumped into the arms of career politicians whose popularity soared in a community that, rightly or wrongly, felt under siege. Our unified, loud, and sometimes violent resistance ended up benefiting Judge Garrity, whose all-white, very well-funded schools in elite Wellesley would never be considered ‘racially imbalanced,’ a term reserved by law for schools that were more than 50 percent ‘minority.’”

MacDonald adds, “To thrive, Bulger needed Southie united in a closed, paranoid, and conspiratorial culture of silence. And for many of our poorest families, that ultimately worked toward our own destruction.”

It is precisely this complicated social background that is conspicuously missing from Black Mass, and would have made for an infinitely better, richer story.