Outlaws: Billy the Kid and Whitey Bulger
The legendary Billy the Kid and the recently captured Whitey Bulger, both Irish American outlaws, share much in common in their lives on the lam.
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.
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?
Billy Bulger, meanwhile, faced harsher questioning about what he really knew about his brother’s whereabouts – and life of crime. Billy had to step down from his post as leader of the Massachusetts state college system and, testifying before Congress in 2003, said: “I now recognize that I didn’t fully grasp the dimensions of his life.”
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