Netflix is now streaming Black Mass, a crime drama boasting a star-studded lineup. Johnny Depp’s real-life gangster role has been highly praised, despite his Black Mass Oscar snub. The movie delves into the controversial alliance or "devil's deal" between notorious gangster Whitey Bulger and FBI agent John Connolly.

Released from prison in the 1960s, Bulger returned to Boston and established a powerful criminal empire. Connolly, a South Boston native, struck a deal with Bulger to help him dismantle the Italian mafia. Black Mass is based on the book of the same name. The authors, two veteran Boston reporters Dick Lehr and Gerard O’Neill, explained it is “a metaphor for the FBI’s corruption, with Bulger as the devil,” (Black Mass movie made him “sick to his stomach,” due to how it compared to the book.

James "Whitey" Bulger Was The Crime Boss Who Led The Winter Hill Gang

Whitey Led The Gang Who Among Other Crimes Helped To Arm The IRA

James “Whitey” Bulger took over leadership of the Winter Hill gang in 1978 when the previous leader, Howard “Howie” Winter, was incarcerated. The gang was a primarily Irish-American organization. Their name is derived from the Winter Hill neighborhood in Somerville, Massachusetts. The surname of Howie Winter is a coincidence. Whitey’s leadership of the gang until 1995 was at the peak of the severity of his crimes, with him gaining the most experience in murder throughout the 1980s. The Winter Hill gang was most known for fixing horse races, as well as supplying weapons to the Irish Republican Army (IRA).

His ascension to leader was made possible because of his protection by the FBI. He had already got away with serious crimes by this point. For example, Frank Capizzi was shot three times by Bulger in 1973. He told this to the FBI when they visited his home. Despite this, Bulger was not arrested. This is because he was a “Top Echelon” informant, which allowed him to evade justice and progress to the top of the rackets. Although he may not have been a direct informant by this point, he had a connection to the FBI via Stephen Flemmi.

Whitey Bulger Became An FBI Informant In The '70s

Bulger, Suspected By None, Was A Top-Echelon FBI Informant

By the time Bulger took over the Winter Hill gang, he had already been an FBI informant since at least 1974 (The Mob Museum). He worked most closely with FBI Special Agent John Connolly, a school friend of Bulger’s. Connolly – or “Zip”, as Whitey Bulger called him – abused his position to share confidential information with his informants, including Bulger, and faced sentencing for this in the early 2000s, along with a retrospective conviction for a more serious crime later on.

Bulger was not the only FBI informant or “rat” within the Winter Hill gang – Stephen Flemmi was also an informant working alongside him. Flemmi is still alive and currently serving a life sentence. Both Flemmi and Bulger provided information on other gangs to the FBI in addition to Winter Hill. Making themselves invaluable to the FBI was important to ensure they stayed protected – when they did not have any important information to report, they made it up to maintain their relationship with the agency.

The Winter Hill Gang's Rivalry With The Patriarca Crime Family Explained

The Two Gangs Had A Fierce Rivalry That Helped The FBI's Motives

The Patriarca crime family, also known as the New England Mafia or the Boston Mafia, is an Italian-American organized crime group operating in New England. With factions based in Providence and Boston, the family has a significant presence in Massachusetts, Rhode Island, and Connecticut. The Patriarca family “were sometimes allies but often rivals with the Winter Hill Gang” (The Mob Museum).

The key difference between the Winter Hill Gang and the Patriarca family was their geographical scope. The Winter Hill Gang was primarily a Boston-based criminal group, while the Patriarca family was part of a national and international crime syndicate. While the Winter Hill Gang was formidable, they couldn't compete with the Patriarca family on a national level. Nonetheless, the two gangs had a fierce rivalry – this ultimately helped the FBI, who used their high-level Irish-American mob connections to go after the Italian mafia, who were a source of obsession for the FBI.

How Whitey Bulger Became A Fugitive

Bulger Was Given A Tip-Off About His Indictment

Bulger’s fate in Black Mass is very difficult to plot in a single film, which is a condensed version. It misses some really interesting material, including Whitey’s 16 years as a fugitive. There are excellent books about it, including The Brothers Bulger by Howie Carr. Bulger vanished on December 23, 1994. Carr details additional events in the days leading up to his absconsion, which provide more backstory. For example, Whitey had been journaling reflecting on his participation in an LSD experiment during his prison years he took part in to reduce his sentence, resulting in terrible nightmares plaguing him throughout his life.

Bulger was able to be a fugitive for so long because he had been anticipating it for some time and prepared his new identity, “Thomas F. Baxter”. He had also received a tip-off, allowing him to make a quick escape, whereas his peers were arrested. The tip-off was from Kevin Weeks, his longtime friend and lieutenant. He telephoned Bulger saying, “We need to talk,” cautious about revealing anything because of the prevalence of phone bugging. Weeks had been given the information of an federal indictment from Zip.

Whitey Bulger's Arrest & Trial Explained

Bulger Was A Most Wanted Fugitive For Over A Decade

Bulger was on the FBI’s Most Wanted list – his poster even briefly appeared in the movie Hannibal, and he was often featured as the fugitive of the week on the TV show America’s Most Wanted. His final capture and the reason behind it is astounding. ABC News reported that the FBI had traced the serial numbers of his girlfriend Catherine Greig’s breast implants back to her plastic surgeon’s office, a vital lead to Bulger’s arrest in 2011. Before this, he lived as Thomas Baxter, a retiree traveling with his partner. He traveled as widely as London without being caught.

Bulger, aged 81, denied involvement in 19 murders...

London was his last credible sighting in 2002, almost a decade before he was finally apprehended. The reward for his capture – $2 million – was the largest reward the FBI had ever offered for a domestic fugitive. Mr. Bulger, aged 81, denied involvement in 19 murders and other criminal activities, including extortion, money laundering, and possession of firearms. After a lengthy trial, Mr. Bulger faced a multitude of racketeering charges, including involvement in 11 murders, in 2013. He was sentenced to life in prison. Judge Denise J. Casper described Mr. Bulger's crimes as “almost unfathomable” due to their extent, cruelty, and wickedness (New York Times Archive).

What Happened To Whitey Bulger & The Winter Hill Gang After His Conviction

Unlike Bulger, Other Winter Hill Gang Were Already Arrested

Whitey Bulger died in a federal prison in West Virginia in 2018 at age 89. He was beaten to death by fellow inmates. This happened only one day after he arrived at the Hazelton Penitentiary. Two of his assailants were mobsters, and it seems likely that the motive behind it was Bulger’s infamous “rat” status. Boston Globe columnist Kevin Cullen’s book points out the suspicion behind the prison’s failure to protect Bulger from these particular inmates. With any number of prisons not containing Boston-area gangsters, it seems suspect that Bulger was transferred to this one considering the risk.

Notable associates in the Winter Hill Gang had already been arrested in the 90s while Bulger was on the run. Kevin Weeks gained the nickname “Two Weeks” because of how quickly he flipped under interrogation. Flemmi was denied comionate release from his life sentence in 2021 (Patriot Ledger) – “The parole board set Flemmi's parole date for the year 2218, saying he has 2,680 months still to serve.” Patrick Nee, a former associate of Bulger and Weeks, was released from prison in 2000. He later wrote the book A Criminal and an Irishman in 2006.

Source: Boston Magazine, Boston, The Mob Museum, New York Times Archive, Patriot Ledger