Just as the infamous South Boston Irish mob boss James “Whitey” Bulger was arrested on June 22, a photo of another outlaw from another century, Billy the Kid, sold for millions of dollars. 

Whitey and Billy were different in many ways. One made his name in the Wild West, while the other ruled gritty urban streets. But it turns out these infamous Irishmen had a lot in common.

Among other things, they spent years on the run from their enemies, and still today show that Americans remain fascinated by mythic outlaws.

Million Dollar Photo

No one would be more surprised than Billy the Kid that his photograph sold for $2.3 million at auction on June 25.

Billy, who was about 20 at the time, probably paid 25 cents to have the picture taken around 1879. The photograph – a tintype, which is an early type of photography that used metal plates – is believed to have been taken outside a saloon at Fort Sumner, New Mexico. The photographer is unknown.

The fragile metal image survived because Billy passed it on to Dan Dedrick, one of his pals, and it stayed in Dedrick’s family until it was consigned by Dedrick’s nephew, Frank Upham, to Brian Lebel’s 22nd Annual Old West Show & Auction in Colorado.

The photo was expected to bring up to $400,000, but it took just over three minutes to get to the $2.3 million mark. The photograph went to collector William Koch, who already has a vast collection of Old West memorabilia, which also includes General Custer’s rifle, as well as guns owned by outlaws Frank and Jesse James.

Born in New York

By most accounts, Billy the Kid was born Henry McCarthy in New York City on November 23, 1859. His mother was Catherine McCarthy. His father has variously been listed as Patrick McCarthy and Patrick McCarthy Bonney. So, it seems quite certain that Billy had Irish blood running through his veins. Ironically, it would be Irish adversaries who would do Billy the Kid in.

In 1870, Catherine moved to Coffeyville, Kansas (although some accounts say she moved to Indiana) with Henry, as well as his brother Joseph, and Joseph’s father William Antrim, whom Catherine later married.

The family later moved to Silver City, New Mexico where Catherine ran a laundry and Antrim worked as a miner. Catherine suffered from tuberculosis, a disease that was rampant in New York City at the time, and it was thought that the drier climate would help her condition. Catherine died, however, in 1873.

According to the website Badhombres, Henry, who was 15 at the time of his mother’s death, didn’t get along with his stepfather and was soon out on his own. He got in trouble for petty theft, but he was also a good student who, according to one teacher, wasn’t in more trouble than any other kid. A reader, Billy the Kid apparently had a penchant for dime novels, which is fitting, as he would later inspire dozens of western adventure stories and movies.

Becoming “the Kid”

The first time Henry McCarthy was called “the Kid” was when he killed an Irishman called Frank P. “Windy” Cahill who had been drinking in George Adkins’ Saloon in Camp Grant, Arizona. Cahill, a huge man, and a blacksmith by trade, called Billy a pimp and hit him across the head, knocking him to the ground. Billy drew a gun and shot Cahill in the stomach. He died a day later.

After that, Billy was on the run and ended up back in New Mexico where he became embroiled in what was known as the Lincoln County War.

According to Dermot P. Duggan, writing in Irish America (October 1991), two Irishmen, L.G. Murphy and J.J. Dolan, owned huge cattle ranches and controlled the town of Lincoln, including the sheriff William Brady. Murphy-Dolan were big suppliers to the U.S. Army and were stealing cattle from another big ranching baron, John Chisum, to fill some of their orders. Billy, after initially working for Murphy-Dolan, met up with John Tunstall, an Englishman who had moved to Lincoln in 1876 and started a ranch on the Rio Felez a few miles from the town. He has also teamed up with Chisum against the Murphy-Dolan outfit.

Billy and Tunstall developed a bond. Tunstall was impressed with Billy and became a father figure to the boy. However, Sheriff Brady’s men, probably at Murphy’s instigation, killed Tunstall in cold blood in February 1878. Billy swore revenge and eventually (with the help of his gang) killed several of Brady’s men. On April 1, 1878, Brady himself was killed.

Enter Pat Garrett

The tit-for-tat killings went on for months. The Governor of New Mexico, Lew Wallace, a former General in the Union Army, put up a reward of $5000 for the capture of Billy. But he also met with him to work out an amnesty in return for his testifying against the cattle thief J.J. Dolan. (His partner L.G. Murphy had died of pneumonia). Billy’s testimony helped convict Dolan, but Wallace wasn’t able to come through on his promise of amnesty for Billy and, shortly after testifying, Billy made his escape.

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.”

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?

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.”