Outlaws: Billy the Kid and Whitey Bulger


And yet, in the end, that’s also what Whitey was. An informant. A snitch. A rat.

“Something Different”

James “Whitey” Bulger was born in Dorchester, Massachusetts in 1929. His father was a laborer but lost his arm in an accident. The family moved into a South Boston housing project at the height of the Great Depression.

“At the time there were no disability pensions, no workmen’s comp, no doles of any sort,” Howie Carr writes in his book The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century.

There were six children in the Bulger home. (“Average sized…by South Boston standards,” Carr quips.) The Bulgers’ father was quiet, especially after his accident, while older siblings Billy and Whitey “would always dominate the family,” according to Carr.

Despite their Depression-era obstacles, Billy and Jack Bulger proved to be strong students.
Whitey, though, went his own way.

“From the beginning, there was something different bout Jim,” TJ English writes in his authoritative book Paddy Whacked: The Untold Story of the Irish American Gangster.

Whitey’s first arrest came at the age of 14. Even when Whitey (so named because of his shock of blond hair) joined the military in the late 1940s, he was reprimanded for getting into several fights.

In and Out of Prison

Bulger spent much of the late 1950s and early 1960s in assorted prisons on robbery and assault charges. This did not deter Whitey, later, from joining the so-called Killeen gang, led by South Boston crime leader Donald Killeen. Killeen was gunned down in 1972, and several Irish-American gangsters have since fingered Bulger in the killing. Whoever whacked Killeen, it put Bulger in the position of rising up the ranks of the rival Winter Hill gang.

It was also around this time that Bulger was approached by the FBI, who knew he was a criminal, but believed he could offer valuable information on other criminals.

“The deal between Bulger and the FBI was deeper, dirtier and more personal than anyone had imagined and it was a deal that was sealed one moonlit night in 1975 between two sons of Southie, Bulger and a young FBI agent named John Connolly,” Lehr and O’Neill write in Black Mass.

Working with the FBI

The Connolly-Bulger relationship was like something out of the Bible: the lawman and the outlaw, both from the same tough Irish streets. Connolly had run into Bulger in an ice cream store way back in 1948. Even then Whitey was a legend, and offered to buy the little kid some ice cream. Awe-struck, Connolly did not know how to respond.

“Hey kid, I’m no stranger,” Bulger said to Connolly, as recounted in Black Mass. “Your mother and father are from Ireland. My mother and father are from Ireland. I’m no stranger.”

Connolly finally relented and requested vanilla.

Bulger and his loyal soldiers consolidated power through the 1980s, making him the most powerful crime figure in New England. One reason he was able to do this was because he could eliminate any criminal competition. He would simply give Connolly and the FBI information on other criminals, then take over their rackets when they were arrested.

Bulger had the best of both worlds. He could control his competition, and yet was also protected by law enforcement. He was also seen as a “king” on the streets of South Boston. “He protected us from being overrun with the drugs and gangs we’d heard about in black neighborhoods,” Michael Patrick McDonald writes. This despite the fact that Whitey had reputedly whacked Irish gangsters and was flooding the streets with drugs, which would decimate a generation of Irish-American youngsters, and made funerals a far too common occurrence for Southie residents.

The End

Bulger’s life was so charmed that in 1991 a story hit the newspapers that a store owned by Whitey had sold a winning lottery ticket. Swiftly, however, the story changed. It emerged that Bulger was actually one of four people who’d purchased the ticket. Whitey Bulger – elusive criminal, local legend – had won $14 million in the lottery. Or at least he’d gotten his hands on the winning ticket.

But even for Bulger, the charmed life could not last. As outlined in Black Mass, FBI agent John Connolly had more or less fallen under Bulger’s spell, to the point that he’d tipped Bulger off that the FBI was about to arrest him in 1994. Bulger fled and began his life on the run. Connolly’s own web of lies unraveled and he was fingered for conspiring with Bulger in 1999 and jailed on numerous other charges.

Bulger remained a free man until June 2011. He will likely spend the rest of his life in prison. But he will live on in books and films and TV shows. And who would be surprised if Bulger, before he dies, gets his hands on, say, one more winning lottery ticket?