Ten unbelievable stories from the wild life of James “Whitey” Bulger

The man and the mythology.
The man and the mythology.
Image: AP/FBI file photo
We may earn a commission from links on this page.

James “Whitey” Bulger was found dead yesterday in a high-security West Virginia prison, where he was serving two life sentences for 11 murders, and had been recently transferred from a Florida facility. The notorious Boston-area organized crime boss was beaten to death by mob-affiliated inmates, the New York Times reports, citing unnamed prison officials.

Bulger was a stone-cold killer, a mob boss, and a larger-than-life figure whose exploits while running the Winter Hill Gang were mythologized in the media, in books, and on the screen. He spent 16 years on the lam, and 12 in second place on the FBI’s Ten Most Wanted Fugitives list, behind only Osama bin Laden.

Here’s a look back at some strange highs and lows in the life of one of America’s most notorious men.

As an FBI informant, he handled his handler

John Connolly was a childhood friend of the Bulger family who later became an FBI agent. He returned to Boston after recognizing “Cadillac” Frank Salemme on the streets of New York City and arresting him.

Three years later, in 1975, Connolly and Bulger made a deal: Bulger would supply the FBI with information on the Italian Mafia if the Feds would guarantee him their protection. The arrangement allowed Bulger to repeatedly escape conviction for everything from horse-race-fixing to gunning down a former henchman in the middle of the day on a Boston street. Connolly also protected Bulger from the law by informing him about possible attempts to bring him to justice.

Eventually, Bulger’s name emerged in an investigation into corrupt ties between the FBI and mob informants, landing Connolly in prison after being convicted of racketeering and second-degree murder.

His brother became one of the most powerful politicians in the state

While Bulger was making a name for himself in the Boston underworld, his younger brother, William Bulger, achieved fame and power via politics.

“Billy” Bulger had a successful career in local politics, eventually serving as the president of the Massachusetts State Senate from 1978 to 1996—winning re-election eight times to achieve the longest tenure in the state’s history. He later became president of the University of Massachusetts, but resigned in 2003 while under pressure after refusing to cooperate with authorities in the hunt for his brother.

He ran away and joined the circus

When Bulger was a teenager growing up in South Boston, the Ringling Bros. and Barnum & Bailey circus came to town. When it left, he went too. As his brother William wrote in his 1996 memoir, “he was in the winds for several months,” working as a roustabout. This circus-specific term refers to a kind of gofer, responsible for putting up, and taking down, the big tent; fetching and carrying; and handling animals and equipment. “He loved it,” William Bulger recalled.

He was recruited as an inmate for LSD trials

Bulger himself wrote last year for Ozy that he was permanently damaged by his participation in drug trials conducted by an Emory University professor while he was an inmate in an Atlanta prison in 1957:

Each week we would be locked in a secure room in the basement of the prison hospital, in an area where mental patients were housed. We went in from 9 a.m. Tuesday to 9 a.m. Wednesday. We were injected with massive doses of LSD-25…In minutes the drug would take over, and about eight or nine men — Dr. Pfeiffer and several men in suits who were not doctors — would give us tests to see how we reacted. Eight convicts in a panic and paranoid state. Total loss of appetite. Hallucinating. The room would change shape. Hours of paranoia and feeling violent. We experienced horrible periods of living nightmares and even blood coming out of the walls. Guys turning to skeletons in front of me. I saw a camera change into the head of a dog. I felt like I was going insane.

He won the lottery—sort of

In 1991, Bulger acquired a winning lottery ticket for $14 million—but he didn’t exactly come across it by chance. Instead, according to a 1995 FBI affidavit, Bulger and two associates each paid around $700,000 to buy the ticket—and $2.3 million of the total winnings—from fellow Bostonian Michael Linskey, in an elaborate money laundering scheme. (The cash itself came from illegal gambling, extortion and loansharking overseen by Bulger and his associates.) Following the FBI investigation, the Lottery Commission eventually froze payments to Bulger’s account. Over the next 20 years, he had been due to receive another $1.9 million.

He hated his nickname, and preferred to go by Jim

Bulger’s nickname, Whitey, was given to him when he was young, due to his shock of white-blonde hair. He tried to shake it off, suggesting Boots as an alternative, but it stuck.

He was turned in by a former Miss Iceland

For more than a decade, Bulger had slipped through the fingers of law enforcement. It took a single phone call from a former beauty queen to eventually bring him down. Anna Bjornsdottir had lived next door to a couple named Charlie and Carol Gasko—the assumed names of Bulger and his girlfriend and fellow fugitive Catherine Greig.

She recognized her neighbors in a 30-second FBI television ad aimed at women watching daytime television, which showed photographs of Greig and Bulger from the 1990s. (Bjornsdottir and Greig had bonded over a love of cats.) She rang the tip line, and eventually landed herself a $2 million tipster’s fee—and put Bulger behind bars.

He’s been played by Johnny Depp and channeled by Jack Nicholson

Though Bulger has served as loose inspiration for many American “mob boss” characters on screens and in books, two major Hollywood productions and a documentary have been directly inspired by Bulger: Black Mass, a 2015 biopic starring Johnny Depp; The Departed, Martin Scorsese’s 2006 crime film starring Jack Nicholson; and Whitey: United States of America v. James J. Bulger, a documentary co-produced by CNN Films.

When The Departed was released, Bulger was still on the run—but he still managed to sneak into a movie theater in San Diego to see the flick, according to the Boston Globe.

He’s a suspect in the biggest unsolved art heist in world history

On March 18, 1990, two thieves disguised as members of the Boston police talked their way in to the city’s Isabella Stewart Gardner Museum in the early hours of the morning. They worked quickly, tying up the guards and making off with 13 masterpieces worth as much as $500 million—Rembrandts, a Vermeer, a Degas, and many others.

Theories abound, and while no connection has been proven, some investigators believe that Bulger was involved in the crime. Charles Hill, a private investigator specializing in art theft and a former detective on Scotland Yard’s art squad, believes the paintings are in the possession of a criminal group in Ireland, and has explicitly pointed to Bulger as the main villain. Though this was partly an “intellectual and visceral” response, he reasoned: “Only Bulger could have done it at the time… Only Bulger had the bureau protecting him. Moving the pictures was easy—most probably in a shipping container with no explosives or drugs for a dog to sniff. He thought Ireland meant safety for him and the museum’s stuff.”

The empty frames that the irreplaceable works were taken from remain hanging at the Gardner Museum to this day, awaiting their return.

He served time in Alcatraz—then went back as a tourist

For four years, between 1959 and 1963, Bulger served time in the infamous San Francisco prison Alcatraz. Then, in the mid-1990s, he went back again as a tourist, while a fugitive from the law. Bulger and his longtime girlfriend visited the site, where they dressed up in striped uniforms and posed for a souvenir photograph behind a set of bars.