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As both the head of Boston’s infamous Winter Hill Gang and an FBI informant, Whitey Bulger made countless enemies — so it came as no surprise when he was killed in grisly fashion in 2018.

Wikimedia CommonsA 2011 mugshot of Whitey Bulger.

James “Whitey” Bulger’s death at the hands of his fellow inmates was a long time coming. Throughout the late 20th century, Bulger led the Winter Hill Gang, a Boston-based crime organization responsible for murders, racketeering, fixing horse races, and drug and arms trafficking.

Bulger eventually fled Boston in the early 1990s once he found himself on the radar of the Federal Bureau of Investigation. For 16 years, Bulger was on the lam, successfully evading capture despite holding a top spot on the FBI’s Most Wanted List. But his good luck eventually ran out in 2011.

Upon his arrest and conviction, Bulger was eventually sent to USP Hazelton in West Virginia, one of the most dangerous prisons in the country.

There, on Oct. 30, 2018, three inmates brutally beat Whitey Bulger to death, closing a brutal chapter in Boston’s long history with organized crime.

Whitey Bulger’s Early Life Of Crime

James Joseph “Whitey” Bulger was born in Everett, Massachusetts in 1929 to parents of Irish descent. When he was a child, his family fatefully moved to South Boston.

Bulger grew up relatively poor, and quickly became swept up in South Boston’s rough crime scene. He reportedly began street fighting at a young age and joined a local gang called the Shamrocks. Then, at the age of just 13 or 14, he was arrested for larceny and sent to a juvenile detention center.

U.S. Attorney’s Office of Massachusetts A young Whitey Bulger.

Upon his release in 1948, Bulger joined the U.S. Air Force, gained his high school diploma, and trained to be a mechanic. From an outsider’s perspective, it appeared that Bulger had turned over a new leaf.

That was far from the case.

In 1952, the military discharged him after he was arrested for going AWOL. Only four years later, Bulger was sentenced to prison for bank robbery.

While in the Atlanta Penitentiary, Bulger claimed to be a victim of the CIA’s MK-Ultra experiment, a disturbing research project involving hallucinogenic drugs and attempted mind control.

Whatever harmful effects this experiment might have had on Bulger, his participation earned him a reduced sentence. He was paroled in 1965 and returned to South Boston, where he began rising in the ranks of the Winter Hill Gang, a powerful Irish Mob organization.

By the late 1970s, Bulger had become the group’s leader. And throughout his reign, he was responsible for countless murders.

Meanwhile, Bulger secretly served as an FBI informant, entering into a corrupt exchange that would protect him from arrest for decades and allow him to exercise greater control over Boston’s criminal underworld.

The tides eventually began to turn on Bulger when an investigation uncovered corruption within the FBI. Authorities started building a case against Bulger under the Racketeer Influenced and Corrupt Organizations Act (RICO).

Boston PoliceA mugshot of Whitey Bulger in 1953.

Bulger’s handler, FBI Agent John Connolly, tipped him off that the agency was finally onto him, and in 1994, Bulger went on the run.

Life On The Lam

For about 16 years, Whitey Bulger was on the run from authorities. His name regularly graced the FBI’s Most Wanted list, right below Osama Bin Laden’s. While at large, Bulger seemingly traveled constantly, stopping in New York, Louisiana, California, Chicago, Florida, and even his hometown of Boston, to name just a few places.

Meanwhile, Bulger was indicted on dozens of counts of various crimes, including racketeering and murder.

Wikimedia CommonsAn FBI surveillance image of Bulger with his partner Stephen Flemmi.

The FBI scoured the country and even searched a handful of foreign countries for Bulger, including Italy, Ireland, France, Brazil, and Thailand. But despite this global manhunt, authorities still had no idea where he might be.

“Here you have somebody who is far more sophisticated than some 18-year-old who killed someone in a drive-by,” FBI agent Scott Bakken told CBS News in 2011. “To be a successful fugitive you have to cut all contacts from your previous life. He had the means and kept a low profile.”

Then, in 2011, an Icelandic woman living in Santa Monica, California called the authorities with a shocking report.

Whitey Bulger’s Capture In California

For a number of years, Anna Björnsdóttir, a former beauty queen and Miss Iceland 1974, split her time between Europe and Santa Monica.

During her stays in California, she had become close friends with Carol Gasko, a woman who lived in the neighborhood with her quiet husband, Charlie. But one day, while watching a news report on wanted criminal Whitey Bulger, Björnsdóttir realized that Charlie Gasko was not the unassuming man she’d originally believed him to be.

Björnsdóttir reported him to the FBI, and on June 22, authorities arrested the “Gaskos,” who were revealed to be Whitey Bulger and his longtime girlfriend, Catherine Greig.

In their apartment, FBI agents found over $800,000, more than 30 guns, and various fake identification documents.

Wikimedia CommonsThe home in California where Bulger was hiding from the law.

During his trial in Boston, Bulger pleaded not guilty to 48 charges relating to murder, obstruction of justice, money laundering, extortion, perjury, racketeering, and weapons violations. He was ultimately convicted of 11 murders, as well as a range of other crimes.

On Nov. 14, 2013, a judge sentenced Bulger to life in prison. At last, the infamous crime boss was behind bars.

Whitey Bulger’s Death At The Hands Of His Fellow Inmates

For most of his sentence, Whitey Bulger was imprisoned at U.S. Penitentiary Coleman II in Florida.

However, at this point, the former mobster was in his 80s, and his health was not what it once was. He reportedly suffered from night terrors and heart issues and required the use of a wheelchair to get around.

His behavior in prison was also poor. On one occasion, Bulger reportedly threatened a female medical worker, and on another, he was caught masturbating in front of a male staff worker. As punishment for these incidents, he was given prolonged stays in solitary confinement.

It was these disciplinary issues that allegedly prompted authorities to transfer Bulger to USP Hazelton on Oct. 29, 2018, despite his medical issues.

The following morning, only about 12 hours after Bulger arrived, prison guards found the 89-year-old dead in his cell.

Security footage recovered from the day of the murder shows two inmates rolling Bulger’s wheelchair into a corner out of the camera’s view, where they, along with a third accomplice, viciously attacked him. The inmates beat him to death with a padlock stuffed in a sock, gouged out his eyes, and attempted to cut out his tongue with a serrated spoon.

“They apparently tuned him up to the point where he was unrecognizable,” said a senior law enforcement official, according to a 2018 New York Times article.

The inmates involved in the attack were identified as 32-year-old Sean McKinnon, a Massachusetts gangster named Paul J. DeCologero, and 51-year-old Fotios “Freddy” Geas — a former Mafia hitman who reportedly hated “rats.”

The Investigation Into Whitey Bulger’s Death

To many, it seemed as though Whitey Bulger’s death was preventable. How could prison officials have allowed a high-profile inmate in poor health fall victim to violence immediately after his transfer?

“I’m not surprised that he got hit,” Ed Davis, a former Boston police commissioner, told the New York Times in 2018. “I’m surprised that they let him get hit.”

In 2022, the Department of Justice released a report detailing several issues with how the Bureau of Prisons managed Bulger’s case.

Public DomainFotios Geas, one of the men accused of murdering Whitey Bulger on Oct. 30, 2018.

The report found “serious job performance and management failures at multiple levels” within the Federal Bureau of Prisons’ handling of his transfer.

Not only did Bureau of Prisons personnel not adequately consider Bulger’s medical condition or properly communicate with one another about the move, but a number of personnel “spoke openly about Bulger’s upcoming arrival in the presence of Hazelton inmates,” despite Bulger’s history and potential risk of harm upon arrival.

The DOJ also found that prison officials failed to properly “assess whether Bulger faced harm from other inmates at Hazelton.”

What’s more, this wasn’t the only time something like this had occurred at Hazelton. The prison had a reputation for being grossly understaffed and dangerous — making it an odd choice for a high-profile inmate like Whitey Bulger.

Indeed, the U.S. Department of Justice listed Hazelton as the second deadliest in the county in their 2024 report, based on the prison’s failure to prevent 14 inmate deaths over the course of eight years.

The Aftermath Of The Murder

A year after Whitey Bulger’s death, his family sued the Bureau of Prisons, alleging that officials had sent Bulger to Hazelton despite knowing the danger he faced there. However, a federal judge dismissed the suit in 2022.

Meanwhile, the three men accused of playing roles in Bulger’s death reached a plea deal in May 2024. Geas and DeCologero, who are accused of bludgeoning Bulger to death, face murder charges. McKinnon, meanwhile, allegedly acted as a lookout during the attack. All three have been charged with conspiracy to commit murder. They will now plead “guilty” in their forthcoming hearings.

For many, the news of Whitey Bulger’s death was more than welcome.

“I hate to be morbid, but knowing the way of person he was, it’s probably a long time coming, seeing that he was responsible for so many other families’ and people’s misery over the years,” an acquaintance of Bulger’s brother told the New York Times. “There’s an old saying, ‘What goes around comes around.'”

“It’s been a long time waiting,” said Patricia Donahue, whose husband was killed in a shooting linked to Bulger in 1982. “Now my family can relax a little bit, now that we don’t have to worry about hearing his name all the time.”

After reading about the death of Whitey Bulger, discover the story of 13 mafia bosses who defined the history of the mob. Then, dive into 27 facts about the life of John Gotti, the infamous crime boss of the Gambinos in New York City.

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