Black Mass Brought the Whitey Bulger Saga to the Big Screen
The 2015 film starring Johnny Depp brings the story of James "Whitey" Bulger's rise to the top of Boston's underworld through the help of fellow gangsters and corrupt FBI agents
Captured
In June 2011, James Joseph Bulger Jr. was arrested by the FBI.
Better known by his nickname “Whitey,” a reference to his blond hair, Bulger had spent the previous sixteen years on the run from the law. He’d worked as an FBI informant since the 1970s and provided US law enforcement with valuable intelligence on his rivals, the New England mafia’s Patriarca family.
But Bulger was certainly no innocent–he had been the leader of the notoriously violent Winter Hill Gang, amassing a long criminal history of his own.
For a time, his FBI handler, John Connolly, protected him from criminal prosecution in exchange for information on the Patriarcas.
In late 1994, Bulger went on the lam after Connolly tipped him off about a pending indictment against him. During his time as a fugitive, Bulger made it onto the FBI’s Most Wanted list–just below Osama bin Laden.
It wasn’t until his trial, following his 2011 capture, that Bulger finally faced justice for his decades of criminal activity.
Bulger’s chaotic double life as a ruthless crime boss, while simultaneously acting as an FBI informant–along with the sixteen years he managed to spend on the run from the law has inspired numerous fictional characters, from Scorsese films to pulp crime television.
Black Mass
In 2015, Director Scott Cooper released Black Mass, a biopic not just inspired by Bulger’s life but based on it.
While Black Mass largely follows Bulger’s story as we know it, the film does dramatize and embellish it in places.
Perhaps most significantly, the film suggests that Bulger’s brother William (played by Benedict Cumberbatch) put him back in touch with Connolly. But Bulger vehemently disputed his brother’s involvement in the matter, claiming that one of his conditions for working with the FBI was that his brother never find out he was doing so.
While William Bulger was by most accounts a law-abiding state senator and cleared of all involvement with his brother’s crimes, Whitey claimed that, as Irish-American South Bostonians, they shared a sense of loathing for police informants.
Meanwhile, Bulger’s former enforcer, Kevin Weeks, disputed the film’s portrayal of Bulger’s son’s death. While Johnny Depp’s Bulger doesn’t go fully off the rails until after his son dies, the real man had ordered plenty of murders long before that point.
Bulger himself took issue with the film, too; while he’d spent decades cultivating a reputation as a “Gentleman Gangster,” Depp portrays him as a psychopathic killer, a traitor to his allies, and a willing accomplice of the FBI.
But it’s not just former gangsters who have been critical of Black Mass; some have argued that the film casts an overly sympathetic eye on men who were accomplices to Bulger’s most heinous acts.
Others, such as Weeks and Flemmi, were also guilty of murder and torture, and Connoly spent decades protecting them from criminal prosecution.
For the average moviegoer, Black Mass is a story about one man’s hideous crimes, but for those familiar with Boston’s criminal history, the real horror is the deep-seated corruption within their own justice system.
Whitey Bulger
James Bulger was born in 1929, the second of six children in an Irish immigrant family.
He grew up in the South Boston housing projects where his family moved to after his father lost an arm in an industrial accident. While several of Bulger’s siblings (including William Bulger, who went on to become an accomplished politician and lawyer) excelled in school, Bulger never took to academics; instead, he jumped straight into a life of crime.
Bulger’s first arrest was in 1943 when he was charged with larceny. Not long after, he joined a street gang known as the “Shamrocks” and began developing a reputation as a skilled thief and street fighter.
In 1956, Bulger served his first-ever term in a federal penitentiary, after being convicted for armed robbery and hijacking a truck.
During his time in the Atlanta Federal Penitentiary, Bulger volunteered to participate in medical experiments which he was told would help to find a cure for schizophrenia. In reality, he had become a human test subject in the MK-Ultra program–a highly secretive CIA operation that sought to identify drugs that could be used to brainwash subjects in interrogations and force confessions.
Over an 18-month period, Bulger, along with several other inmates, was repeatedly dosed with LSD. He kept his hallucinations while on the drug a secret from the doctor and attendants present at the trials, out of fear that he would be “committed for life.”
In 1965, after nine years in prison, Bulger’s third petition for parole was granted.
Boston Gang Wars
After his release from prison, Bulger wove his way into the Killeens, a notorious South Boston crime family.
In 1971, a turf war between the Killeens and the rival Mullen gang led to a string of killings throughout Boston and its suburbs. The older Killeens initially found themselves outmanned and outgunned, but Bulger intended to take matters into his own hands.
Initially, he had set out to kill Mullen member Paul McGonagle. But, in a case of mistaken identity, Bulger accidentally shot McGonagle’s law-abiding brother, Donald, instead.
As an act of revenge, Paul murdered Bulger’s mentor and fellow Killeen member, Billy O’Sullivan, under the assumption that he was responsible for Donald’s death.
The Killeens fled Boston for a time out of fear of further retaliation. But, upon their return, they attended a meeting with leadership from the Mullens and the larger Winter Hill Gang.
The three gangs agreed to join forces, with Howie Winter, leader of the Winter Hill Gang, as the boss.
Whitey spent the following years climbing the ranks of the Winter Hill Gang–and, when Winter and several members of his inner circle were arrested for fixing horse races in 1979, Bulger was perfectly positioned to step into the power vacuum and seize control.
It was also during this time that Bulger’s son tragically died of Reye syndrome (a brain disease triggered by aspirin) at the age of 6.
Boston’s Criminal Underground
From the early 1900s through the late 1970s, Boston’s underworld was controlled by two powerful, vying criminal organizations –the Italian Patriarca family, and the mainly Irish Winter Hill Gang.
Both groups made their fortunes off of various criminal rackets–illegal gambling, loan sharking, trafficking of stolen goods, and seedier areas like pornography and narcotics sales.
It wasn’t just illegal and unethical “business” activity that caught the attention of US law enforcement agencies, though.
What made organized crime especially dangerous was its insular nature and the ruthlessness with which mob bosses defended what they believed belonged to them.
Members of the Italian Mafia operated under the principle of omertà–or, silence in the face of the law. Rather than seeking legal reparations for injustices against them, mafiosos were expected to turn toward the Mafia family and its own twisted form of justice. It is for this reason that many Mafia crimes remain unsolved to this day.
But omertà was not an unbreakable code. The FBI managed to utilize well-placed criminal informants, including Bulger, who could give them valuable information that helped disrupt the New England mafia.
And it was thanks to these informants that, by the late 1970s, organized crime in the US finally began to decline.
Bulger the Informant
The FBI first attempted to recruit Bulger in 1971. He was initially approached by Special Agent John Connolly, an old childhood friend.
Connolly failed to win Bulger’s trust–but just a few years later, Bulger’s partnership with Winter Hill enforcer & FBI informant Stephen Flemmi led him back into the agency’s arms.
During a late-night conversation with Connolly, Bulger agreed to work with the FBI, with the mutual goal of taking down the Patriarca family.
“If they want to play checkers,” he reportedly told Connolly, “we’ll play chess.”
In later court depositions, Bulger’s affiliates claimed that the vast majority of information provided to the FBI came from Flemmi.
However, Connolly would sometimes put Bulger’s names on the files to justify his value as an informant.
Connolly reasoned, he could justify his continued meetings with Bulger–and keep him protected from criminal prosecution by exaggerating Bulger’s usefulness to the bureau.
When FBI supervisor John Morris was placed at the Boston field office, Connolly briefly feared that Morris would rein in his protection of Bulger–but before long, Morris had become their accomplice.
Tensions between the Winter Hill Gang and the Patriarcas continued to escalate until the conflict finally came to a head in 1983.
The Boston Police Department raided a Winter Hill-affiliated butcher shop, on a tip that a kidnapped employee of a coin-op laundry shop owned by the Patriarcas was being held there. They found the victim hanging from a beef rack with severe torture-inflicted injuries.
The conflict (and Morris’s incompetent management of the case) triggered an internal FBI investigation, while the press speculated about potential corruption. Prior to that point, it was unheard of for a criminal of Bulger’s status to remain at large for years without a single arrest.
By 1988, news had officially broken that Bulger was under the FBI’s protection as an informant.
Not long after, the DEA, state, and local police indicted Bulger for extortion, racketeering, drug trafficking, and murder.
There was no debating the matter anymore; the FBI had been compromised.
Payback and Death
Though they would of course deny it, it was fairly obvious for anyone with the eyes to see that since Bulger had thoroughly embarrassed and exposed the US government and their criminal activities, the feds were looking for some payback.
Their chance came in late October of 2018 when the Federal Bureau of Prisons transferred the then 89-year-old Bulger from a federal facility in Oklahoma to the notoriously dangerous U.S. Penitentiary in Hazleton, West Virginia.
Bulger was there for less than a day before the wheelchair-bound gangster was brutally murdered by inmates. He had been beaten with a padlock wrapped inside a sock, and his eyes and tongue had nearly been removed.
Bulger’s death was the third homicide at the facility in less than two months. Many people openly stated that Bulger had deliberately been placed in harm's way as retribution by the US government for exposing their blatant corruption.
Just prior to Bulger’s death, correctional officers from Hazleton prison had told members of Congress about the extreme and dangerous atmosphere at the prison. This removed any plausible deniability that the government may try to plead.
Bulger’s family filed a wrongful death suit against the Justice Department. However, the lawsuit was dismissed.
James Bulger was buried in St. Joseph’s Cemetery in West Roxbury, Boston.
Sources:
Bulger, James. “I Was a Guinea Pig for CIA Drug Experiments.” Web.archive.org, OZY, 30 Oct. 2018, web.archive.org/web/20181030231252/www.ozy.com/true-story/whitey-bulger-i-was-a-guinea-pig-for-cia-drug-experiments/76409. Accessed 17 June 2024.
Child, Ben. “Real-Life Gangsters Pour Scorn on Johnny Depp Mob Biopic Black Mass.” The Guardian, 21 Sept. 2015, www.theguardian.com/film/2015/sep/21/real-life-gangsters-scorn-johnny-depp-black-mass-whitey-bulger. Accessed 17 June 2024.
Dockterman, Eliana. “The True Story behind “Black Mass.”” Time, 21 Sept. 2015, time.com/4043186/black-mass-true-story/.
Landsbaum, Claire. “Here’s What’s Fact and What’s Fiction in Black Mass.” Slate, 23 Sept. 2015, slate.com/culture/2015/09/black-mass-accuracy-whats-fact-and-whats-fiction-in-the-james-whitey-bulger-biopic.html.
Wikipedia Contributors. “Whitey Bulger.” Wikipedia, Wikimedia Foundation, 7 Sept. 2019, en.wikipedia.org/wiki/Whitey_Bulger.