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.

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The only known photo of Billy the Kid and an early mug shot of Whitey Bulger.

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Next year, we will see yet another Billy the Kid flick, this one called Birth of a Legend: Billy the Kid and the Lincoln County War.

The Outlaw from Southie

At the time that Billy the Kid’s photo was getting set for auction, a judge was asking legendary South Boston mob boss Whitey Bulger if he could pay for his own lawyer.

“Well, I could, if you give me my money back,” Bulger quipped, referring to $800,000 in cash found in the wall of an apartment in Santa Monica, California, where he had been living for years with his girlfriend. A more poignant scene unfolded a few days later, when Whitey “smiled slightly” at his two brothers, John and William (long the most powerful politician in Massachusetts), who sat in on one court session, according to The Wall Street Journal.

Whitey Bulger’s downfall finally brought an end to an Irish-American tragedy, one that begins in the impoverished housing projects of South Boston and detours horrifically into a netherworld of drugs and murder, where even FBI agents were willing to work for the bad guys. Along the way, many people died, there were attempts to run guns to the IRA, rumors swirled that the “good son” Billy Bulger may not be so good, and Whitey just vanished for over a decade.

Public Enemy Number One

At the time of his capture, Bulger was Public Enemy Number One, at the top of the FBI’s Most Wanted list ever since Osama bin Laden was killed. And yet, even as Hollywood movies based on his crimes were made, Bulger eluded authorities. Phantom Whitey Bulger sightings were reported from Ireland to his native South Boston.

Not unlike some legend of the Old West, the less we actually knew about Bulger, the more fascinating he seemed to become.

The Bulger myth had already swelled to epic proportions in 2006, with the release of the Martin Scorsese film The Departed. Jack Nicholson played ruthless Boston Irish mob boss Frank Costello, who had more than a few things in common with Bulger. The Showtime TV series Brotherhood was also about a New England Irish crime boss whose brother was a powerful politician. (Billy Bulger was president of the Massachusetts State senate for years.)

Meanwhile, Hollywood rumors continue to swirl that Irish cinematic royalty Jim Sheridan and Daniel Day-Lewis will make a movie about Bulger, and how he manipulated law enforcement officials before he vanished in 1997.

Aside from movies and TV shows, Bulger has inspired enough books to line a long shelf.

“No One Made Us Feel Better”

How did Whitey Bulger become such an outlaw, as well as a mythic character?

“No one made us feel better about where we lived than Whitey Bulger,” Michael Patrick McDonald writes in All Souls, his lyrical, heartbreaking memoir of growing up in South Boston. “Whitey was the brother of our own Senator Billy Bulger, but on the streets of Southie he was even more powerful than Billy. He was the king of Southie, but not like the bad English kings who oppressed and killed the poor people of Ireland. No way would we put up with that.”

Of course, as McDonald’s book makes clear, that’s exactly what Bulger was doing.

He was instilling the Irish of Southie with local pride, only to later sell them lethal drugs or recruit them for criminal business, then dispose of them when they were no longer useful. Bulger and his associates also knew how to stir up fears against outsiders, including African Americans, which culminated in the infamous 1970s school busing riots.

But there is more. As Dick Lehr and Gerard O’Neill write in their excellent book Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob, Whitey Bulger was indeed a “gangster with a reputation as the ultimate stand-up guy.”

There was nothing worse in Southie than a snitch, a rat. To be an informant “defied the culture of [Whitey] Bulger’s world, South Boston, and his heritage, Ireland.”

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.

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