Outlaws: Billy the Kid and Whitey Bulger


In 1880, fellow Irish American Pat Garrett was made sheriff of Lincoln County and he managed to capture Billy, but he couldn’t hold him for long. A couple of months later, on July 13, 1881, Billy had another run-in with Garrett at the house of his friend Pete Maxwell and Garrett shot him dead. Billy was unarmed.

A Hollywood Legend

Billy the Kid’s death turned out to be merely the first act of his longer, mythic life. His exploits would inspire countless books, plays and radio specials. Meanwhile, generations of Hollywood’s most celebrated talent created films based on Billy the Kid. In the 1930s and 1940s, King Vidor, Wallace Beery, Roy Rogers, Buster Crabbe and Howard Hughes were among the actors and directors who made films about Billy the Kid and Pat Garrett.

Paul Newman, Kris Kristofferson, Val Kilmer and Emilio Estevez (son of Irish American Martin Sheen) are among the stars who portrayed Billy the Kid in subsequent films.

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.”