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The Crimes of Gangster James “Whitey” Bulger

I've spent half a century writing for radio and print (mostly print). I hope to still be tapping the keys as I take my last breath.

Whitey Bulger's mugshot from 1959.

Whitey Bulger's mugshot from 1959.

James "Whitey" Bulger

James Bulger was born into an Irish-American family in 1929. He grew up in gritty South Boston in a family that was no stranger to poverty. He got the nickname “Whitey,” which he hated, because of his blondish hair as a child.

While his siblings did well at school, James preferred life on the streets and took to crime at an early age, with his first arrest coming at age 14.

He started with shoplifting and stealing from the back of trucks making deliveries, and soon he was involved with a street gang engaged in assaults and robbery. A favourite activity was to lure homosexuals, who would be beaten up and relieved of their valuables.

Bank Robbery

In the early 1950s, Whitey Bulger pulled a series of armed bank robberies. But he and his fellow crooks were not very accomplished and soon they were caught.

In 1956, Whitey drew a 25-year sentence and served part of it in the infamous Alcatraz Prison. He got out after nine years and returned to Boston having learned all he needed to know to survive in the underworld.

Boston Gang Warfare

Several Irish-American gangs operated in South Boston running loan-sharking, extortion, and bookmaking rackets.

At the top of Boston’s crime hierarchy was the Italian Mafia that controlled North Boston under boss Raymond Patriarca; all the Irish gangs paid tribute to the Patriarca family.

The Killeen Gang was led by Donald Killeen and Bulger went to work for him as an enforcer. The Mullen Gang under the leadership of Paulie McGonagle was in the same line of work and the two outfits clashed from time to time.

Raymond Patriarca.

Raymond Patriarca.

In 1971, a Killeen associate bit off the nose of Michael Dwyer, a member of the Mullen Gang. That gruesome event triggered an all-out war with bodies turning up throughout Boston and the surrounding area.

Whitey Bulger was in the thick of the gunfire, but he realized he was on the losing side. So he made a bold move. He met secretly with Howie Winter, boss of the Winter Hill Gang and, allegedly, told him he could stop the gang war by taking out the Killeen leaders.

On May 13, 1972 someone emptied most of the contents of a machine gun’s magazine into the face of Donald Killeen.

It's always been suspected that the "someone" was Whitey Bulger.

The Winter Hill Gang

After the murder of Donald Killeen, a truce was called in the gang war and Whitey Bulger joined the Winter Hill Gang. He rose quickly through the ranks as a go-to guy when what’s known in criminal circles as “wet work” needed to be done.

The list of dead bodies attributed to him includes mobsters Spike O’Toole, Paulie McGonagle, Eddie Connors, Tommy King, and Buddy Leonard. There were many others.

In 1979, Howie Winter went to prison after a conviction for fixing horse races. Whitey Bulger was also deeply involved in race-fixing yet he avoided prosecution and succeeded Winter at the head of the gang. He was now the undisputed king of South Boston’s Irish-American organized crime.

FBI surveillance photo of Whitey Bulger (right) with one of his close associates Stephen Flemmi.

FBI surveillance photo of Whitey Bulger (right) with one of his close associates Stephen Flemmi.

Whitey Bulger’s Double Life

There was a reason Whitey Bulger avoided indictment on rigging horse races.

Some childhood friends of Bulger’s had chosen a different path and had gone into law enforcement; one of them was FBI agent John Connolly. James’s younger brother, William, had also chosen a less criminal career and had taken up politics, being elected President of the Massachusetts State Senate in 1978.

These connections led Whitey into the arms of the FBI and its Top Echelon Program (TEP).

The TEP was set up to infiltrate the Mafia and find informants on the inside. Whitey had lots of links with the Patriarca family but resented the supremacy of the Mafia and the need to share territory with them.

So when the FBI offered him a deal, he was happy to tell what he knew about Patriarca in exchange for federal police protection. It was also an attractive opportunity to take down a rival and have sole possession of Boston’s criminal world.

Bulger’s controller was John Connolly and he kept his old friend safe from prosecution.

When Boston police investigated Bulger for drug trafficking, murder, or other serious crimes, a directive would come from Washington to back off. Whitey was able to continue with his criminal enterprises with impunity right under the noses of local law enforcement.

In 1986, the FBI was able to smash the Italian Mafia organization in Boston and Whitey emerged as the city’s top organized crime boss.

Under his leadership, it’s alleged that at least 18 murders took place while the FBI told everybody in law enforcement to look the other way.

Whitey Bulger Vanishes

As head of organized crime in Boston, Whitey Bulger expanded into the drug trade and this attracted the attention of another federal group, the Drug Enforcement Agency (DEA).

The DEA got a lucky break when agents found a drug trafficker who got into a deal with Bulger that went wrong and he ended up owing the crime boss $100,000. The dealer knew he was a dead man if he didn’t get help so he turned to the DEA in exchange for protection.

In August 1990, the dealer’s information led to the arrest of more than 50 members of Bulger’s drug ring. The FBI continued to keep Bulger safe, although his time was running out as his chief protector, the FBI’s John Connolly, had retired.

In the early 1990s, the DEA and the Massachusetts State Police gathered evidence that Whitey Bulger was engaged in money laundering and extortion. In December 1994, John Connolly, in touch with ex-colleagues, got wind of the investigation and tipped Bulger off. The gangster quickly disappeared.

Whitey Bulger later in life.

Whitey Bulger later in life.

Global Manhunt

James “Whitey” Bulger appeared on America’s Most Wanted Fugitives list in 1999, at one point placing second only to Osama bin Laden. But he eluded capture until 2011.

He was tracked down to Santa Monica, California where he was living quietly in an apartment with his girlfriend Catherine Greig. FBI agents also found more than $800,000 in cash, 30 firearms, and a bunch of fake IDs.

Hauled back to Boston, Bulger faced 33 indictments, including taking part in 19 murders. There were also racketeering, extortion, money laundering, drug dealing, and other charges to answer.

After a two-month trial, in April 2013 a jury found him guilty of most of the charges. U.S. District Judge Denise Casper summed up the opinion shared by law-abiding citizens of James “Whitey” Bulger: “The scope, the callousness, the depravity of your crimes are almost unfathomable.”

She handed Bulger two life sentences plus five years. In late October 2018, he was found dead, apparently killed by someone, in his cell in a West Virginia maximum security prison. He was 89 years old.

In August 2022, three men were charged with the murder of Bulger. One of the accused is believed to be a Mafia hitman.

Bonus Factoids

  • Gangster Howie Winter once said of Bulger he was so clever “he could teach the devil tricks.”
  • According to one of Whitey Bulger’s enforcers, Kevin Weeks, Christmas gifts to police officers ensured the organization enjoyed a business-as-usual New Year: “Each December Jimmy would send us out with envelopes stuffed full of money and luxurious gifts . . . Jimmy always said Christmas was for cops and kids” (The Mirror).
  • In 1991, Whitey Bulger held a winning ticket in the Massachusetts state lottery worth $14.3 million. The ticket had been bought by Michael Linskey in one of Bulger’s liquor stores. Mystery surrounds how Bulger and his associates “came into possession” of the ticket, but it seems Linskey might have been “persuaded” to cut Whitey and a couple of friends in.


© 2017 Rupert Taylor


DDE on January 29, 2018:

What a character and to have lived as if nothing bothered him. Informative and I learned lots about Whitey Bulger