True crime biopics are all the rage at the moment. In recent weeks, Netflix series Narcos, which depicts the life of cocaine kingpin of all kingpins Pablo Escobar, has risen in popularity. Today, another work inspired by a real-life gangster hit theaters in the form of Black Mass. In this film, Johnny Depp portrays reputed boss of Boston’s Irish mob, “Whitey” Bulger. From the 1970s into the new millennium, Bulger ruled the streets of Boston, mainly due to his status as a federal informant with the FBI. Just think Jack Nicholson as Frank Costello in The Departed. The character is loosely based on Bulger.
James Joseph “Whitey” Bulger, Jr. was born in 1929 and came up in the Mary Ellen McCormack Housing Project (now called the Old Harbor Village Public Housing Project) in South Boston. While his brothers had scholarly ambitions, Whitey was drawn to streets and made a name for himself as a thief and vicious brawler. He eventually joined an Irish-American gang called the Shamrocks. In 1943, at the age of 14, Bulger was arrested for the first time on larceny charges. later, he would catch assault, forgery and armed robbery charges and was sentenced to juvenile hall.
Upon his release in 1948, Bulger joined the Air Force and was stationed in Kansas, then Idaho where he served as an aircraft mechanic. However, his street instinct was still keen and he caught several charges for assault and was placed in the stockade as punishment. He was also arrested in 1950 for going AWOL. Nevertheless, he was still able to leave the service with an honorable discharge in 1952.
Unable to straighten his life out, Bulger was convicted on his first federal charges for armed robbery and truck hijacking and was sent to Atlanta Penitentiary in 1956. Here, he is said to have been a lab rat in the MK Ultra program along with 18 other prisoners for 18 months. In this program, Bulger and the others were given LSD and other drugs as they were tested as mind-control substances by the CIA. Bulger says that they were misled to believe that the government was searching for a cure for schizophrenia. He said the experience to him “to the depths of insanity.” Bulger was transferred from Atlanta Penitentiary to Alcatraz in 1959, then to Leavenworth, then to Lewisburg, before being paroled in 1965. He had served nine years.
After his release, Bulger had a short-lived career in maintenance and construction. It wasn’t long before he became a bookmaker and loanshark under Donald Killeen, boss of the South Boston Irish mob. A war broke out with the rival Mullen Gang after Killeen’s younger brother chomped the nose off of Mullen Gang member Michael Dwyer. During this war, Bulger caught his first body, killing Donald McGonagle after mistaking him for his brother, Paulie. Paulie McGonagle then killed Bulger’s mentor Billy O’Sullivan, believing him to be his brother’s murderer. The Mullen Gang had the upper-hand and Bulger knew it, so he, allegedly went to Howie Winter, leader of the Winter Hill Gang, and advised him to kill the Killeens. Donald Killen was killed outside of his home in 1972, but former boss of the Mullen Gang Patrick Nee says that his crew was responsible for the murder.
Shortly after, Nee invited Bulger was invited to a sitdown, mediated by Howie Winter and Joseph Russo, capo in the Italian Patriarca crime family. After this meeting, over steak and ginger ales, the gangs merged with Winter overseeing everything. Bulger pulled up on Killeen’s sole surviving brother, Kenneth as he jogged in Boston’s City Point neighborhood with his Winter Hill Gang enforcers Stephen Flemmi and John Mortorano and warned him saying, “It’s over. You’re out of business. No more warnings.”
Bulger and the Mullens gang controlled the criminal underworld in South Boston after that. In 1973, they were known to shakedown bookies and loansharks. Bulger would also advise his boss, Winter, to off anyone who got out of pocket. In 1979, Winter and many of his associates were indicted on charges stemming from horse race fixing. Bulger and Flemmi were left out of the indictments, and Bulger seized control of the Winter Hill Gang.
The reason Bulger and Flemmi were not indicted can be credited to their status as FBI informants. In 1971, FBI personnel approached Bulger in hoped he would cooperate against the Patriarca family, but he denied them. However, FBI special agent John Connolly was successful in recruiting him in 1974 after Bulger teamed up with Flemmi, who had been working with the feds since 1965. Connolly convinced Bulger that he could be a valuable asset to him in his feud with Patriarca underboss Gennaro Anguilo. Bulger’s response to Connolly’s pitch was, “Alright, if they want to play checkers, we’ll play chess. Fuck ’em.” According to Connolly, “The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them.” From then on, both sides exchanged intelligence. Bulger also lavished the feds with expensive gifts and cash. In a 2011 interview, Flemmi said, “Me and Whitey gave them shit, and they gave us gold.”
Bulger and the Winter Hill gang were immune from the law, and flourished. The Patriarca family lost control of their rackets after a 1986 RICO indictment sunk Anguilo and other top brass. Bulger also gave up members of his own organization who he viewed as problems.
Throughout the 1980s, Bulger, Flemmi and Kenneth Weeks ran Boston through extortion, loansharking, bookmaking, truck hijakcing and weapons dealing. Employees of the Boston Police Department and Massachusetts State Police were also bought off. Bulger was viewed as a drug dealer, but he never really was. He shook-down drug dealers. He would call the top dealers in Boston to his headquarters and demand that they pay him for the privilege of making money in his town. Bulger allowed cocaine and marijuana dealers to live, but shut down heroin and PCP rings. He also forbade the sale of drugs to children. It is said that Bulger made $30 million extorting drug dealers.
One of the most daring deals that Bulger made was one with the infamous Irish Republican Army (IRA), an outfit he claimed he’s never roll on. In the early ’80s, after a meeting with IRA Chief of Staff Joe Cahill, Bulger and Nee raised a million dollars by shaking down drug dealers. The used this money to buy weapons to ship to the IRA. 91 rifles, eight submachine guns, 13 shotguns, 51 handguns, 11 bulletproof vests, 70,000 rounds of ammunition, “plus an array of hand grenades and rocket heads.” Bulger also procured C-4 explosives. All of the weaponry was loaded into a Valhalla van on a ship to sail across the Atlantic to Ireland. However, thanks to an informant, the van was intercepted by the Irish Navy and members of the IRA were arrested. One of the crew members named John McIntyre was arrested, and he implicated Bulger. FBI agent Connolly overheard and told Bulger, who murdered him, assisted by Flemmi.
In 1991, Bulger and three other men won the Massachusetts State Lottery on a ticket purchased in one of Bulger’s stores. The $14 million come-up is believed to be obtained illegally.
The beginning of the end was the 1994 probe into Bulger’s gambling operations by the DEA with state and local police. The FBI was not involved because they were proven to be compromised by Bulger. When the authorities got several bookies to admit that they answered to Bulger, a RICO indictment was handed down. Connolly informed Bulger that the indictments were coming and he fled Boston. He eluded the feds, here and abroad, for 16 years, 12 of them on the FBI’s Most Wanted Fugitives list. The $2 million reward on his head is second only to the reward wanted for the capture of Osama Bin Laden. He was captured by the Bulger Fugitive Task Force (FBI agents and a Deputy US Marshal) on June 22, 2011. He was charged with murder, “conspiracy to commit murder, extortion, narcotics distribution and money-laundering.” When they got him, a search of his apartment yielded more than $800,000 in cash, 30 guns and fake IDs. In 2013, Bulger was charged with 32 counts of racketeering, money laundering, extortion, and firearms possession. Included in the racketeering charges were 19 murder counts. A number of his associates, including Flemmi and Weeks, testified against him. Two months later, Whitey Bulger was convicted of 31 of the 32 counts. He was convicted for 11 of the murders. The judge handed down a sentence of two terms of life, plus five years.
The FBI didn’t get off Scott-free either. Connolly was convicted and jailed in 2002. In 2006, the department was embarrassed when a federal judge ruled that the Bureau mishandled Bulger and Flemmi and blamed them for the 1984 murder of McIntyre. McIntyre’s family received a $3 million award from the government.
This isn’t everything, but it should give you a good sense of who the man depicted in Black Mass, if you plan on going to theaters to see it. We haven’t seen too many gangsters like Whitey Bulger in our lifetimes and we won’t see too many more like him.