Whitey Bulger
Based on Wikipedia: Whitey Bulger
The FBI's Most Dangerous Partnership
For sixteen years, one of America's most ruthless crime bosses hid in plain sight in a Santa Monica apartment, walking on the beach and paying rent in cash while the Federal Bureau of Investigation hunted him across the globe. James "Whitey" Bulger was second only to Osama bin Laden on the FBI's Most Wanted list. The bitter irony? He'd spent decades as the bureau's prized informant, protected by the very agents now tasked with finding him.
This is the story of how the FBI made a deal with the devil—and the devil collected.
South Boston's Native Son
Whitey Bulger was born in 1929, the second of six children in a family that knew hardship intimately. His father, an Irish immigrant from Newfoundland, lost his arm in an industrial accident while working as a union laborer on the Boston docks. The family tumbled into poverty.
In 1938, when Whitey was nine, the Bulgers moved into the Mary Ellen McCormack Housing Project in South Boston—a neighborhood that would define his entire criminal career. South Boston, or "Southie" as locals called it, was a tight-knit Irish enclave where loyalty meant everything and outsiders were viewed with suspicion.
The Bulger children took different paths. William Bulger excelled academically, eventually becoming president of the Massachusetts Senate—one of the most powerful politicians in the state. John Bulger also stayed on the right side of the law. But James Jr. was drawn to the streets like iron to a magnet.
He hated the nickname "Whitey," earned from local cops who noticed his shock of blond hair. He preferred "Jimmy" or even "Boots"—this last one from his habit of wearing cowboy boots with a switchblade hidden inside. By fourteen, he'd been arrested for larceny. By his late teens, he'd accumulated charges for assault, forgery, and armed robbery. The juvenile reformatory couldn't hold him.
A Brief Military Interlude
In 1948, Bulger joined the United States Air Force. On paper, it should have been a fresh start. He earned his high school diploma and trained as a mechanic. But the regimented military life couldn't tame him.
He spent time in military prison for assaults. He went absent without leave. In 1951, stationed at Malmstrom Air Force Base in Montana, he was arrested and charged with rape after being caught in a hotel room with a fifteen-year-old girl.
Somehow, he still received an honorable discharge in 1952. He returned to Massachusetts, where his real education was about to begin.
The CIA's Guinea Pig
In 1956, Bulger landed in Atlanta Penitentiary for armed robbery and truck hijacking. What happened there would haunt him for the rest of his life—and remains one of the most disturbing chapters in American government history.
Bulger became a test subject in MK-ULTRA, the Central Intelligence Agency's secret program exploring mind control through psychoactive drugs. The program's existence wasn't publicly confirmed until years later, when CIA documents emerged proving what had long been suspected.
Here's how it worked: Inmates were told they were helping to find a cure for schizophrenia. In exchange for participating, they'd receive reduced sentences. Nineteen prisoners, Bulger among them, volunteered.
For eighteen months, they were given LSD and other experimental drugs.
Bulger described the experience as "nightmarish." In his notebooks, he wrote that it took him "to the depths of insanity." He heard voices. He feared that if he admitted this to anyone, he'd be committed to a mental institution for life.
The government had recruited him by deception, he later complained. And he was right. MK-ULTRA would eventually be exposed as one of the most egregious violations of medical ethics in American history, involving not just prisoners but also unwitting civilians who were dosed with LSD without their knowledge or consent.
Alcatraz and Education
In 1959, Bulger was transferred to the most famous prison in America: Alcatraz Federal Penitentiary, sitting on its rocky island in San Francisco Bay. The prison that had held Al Capone would now hold the man who would become Boston's answer to Capone.
Bulger surprised everyone. Rather than simply serving time, he improved himself. He lifted weights obsessively. He enrolled in correspondence courses—typing, bookkeeping, business law. He devoured books on poetry, politics, and military history.
He was learning the tools he'd need to run a criminal empire.
After transfers to Leavenworth and then Lewisburg penitentiaries, Bulger was finally paroled in 1965 after nine years behind bars. He was thirty-six years old, hardened by prison, educated by the state, and traumatized by the CIA.
He wouldn't be arrested again for forty-six years.
The Killeen Wars
Bulger returned to South Boston and started at the bottom—janitor work, construction. But he quickly moved into more lucrative pursuits: bookmaking and loan sharking under Donald Killeen, whose gang had dominated South Boston's underworld for two decades.
The Killeen organization was a family affair. Three brothers—Donnie, Kenny, and Eddie—ran operations out of the Transit Café, alongside lieutenants Billy O'Sullivan and Jack Curran. For years, they'd had Southie's criminal rackets locked up.
Then came the Mullens.
The Mullen Gang was younger, hungrier, and spoiling for a fight. In 1971, Kenny Killeen allegedly shot and brutally beat a Mullen member named Mickey Dwyer during a brawl at the Transit Café. The incident sparked a full-scale gang war.
The Killeens quickly discovered they'd underestimated their rivals. The Mullens were better organized, more ruthless, and more willing to kill. Bodies started turning up across Boston and its suburbs.
A Case of Mistaken Identity
During this war, Bulger committed what his later associate Kevin Weeks described as his first murder. The target was Paul McGonagle, a Mullen member who'd been running his mouth.
Bulger shot his target right between the eyes.
Only it wasn't Paul McGonagle. It was his brother Donald—a law-abiding citizen who had nothing to do with the gang war.
According to Weeks, Bulger drove straight to Billy O'Sullivan's house to confess his mistake. O'Sullivan's response was chillingly casual: "Don't worry about it. He wasn't healthy anyway. He smoked. He would have gotten lung cancer."
The real Paul McGonagle, believing O'Sullivan was responsible for his brother's death, later ambushed and killed him. The violence was feeding on itself.
The Winter Hill Solution
Bulger could see which way the wind was blowing. The Killeens were losing. Rather than go down with the ship, he allegedly approached Howie Winter, leader of the Winter Hill Gang—a powerful organization based in Somerville, just northwest of Boston.
Bulger reportedly offered to end the war by murdering the Killeen leadership himself.
On May 13, 1972, Donald Killeen was gunned down outside his home in Framingham. The killing has been attributed to Bulger, though former Mullen boss Patrick Nee disputed this, claiming Killeen was actually murdered by Mullen enforcers.
Either way, Bulger had positioned himself perfectly.
Nee arranged a sit-down at Chandler's nightclub in Boston's South End. The meeting was mediated by Howie Winter and Joseph "J.R." Russo, a captain in the Patriarca crime family—the Italian-American Mafia organization that controlled organized crime throughout New England from its base in Providence, Rhode Island.
The Mullens sent Nee and Tommy King. The Killeens sent Bulger. The outcome? Both gangs merged under Winter's leadership, with Bulger firmly in the fold.
Soon afterward, Bulger encountered Kenny Killeen—the last surviving Killeen brother—jogging through Boston's City Point neighborhood. Bulger called him over to a car and delivered a simple message: "It's over. You're out of business. No more warnings."
In the car with Bulger sat Stephen Flemmi and John Martorano—two men who would become central to everything that followed.
The Devil Teaching Tricks
By the early 1970s, Bulger and the Mullens controlled South Boston's criminal underworld. The FBI took notice. An agent named Dennis Condon logged that Bulger and Nee were "heavily shaking down the neighborhood's bookmakers and loan sharks."
Bulger proved himself invaluable to Howie Winter. He had a gift for manipulation—for convincing the boss to sanction the elimination of anyone who "stepped out of line."
In a 2004 interview, Winter recalled that the highly intelligent Bulger "could teach the devil tricks."
Bulger's victims during this period included former Mullen colleagues who'd once fought alongside him: Paul McGonagle (finally getting the right brother), Tommy King, and James "Spike" O'Toole.
The Tommy King murder illustrated Bulger's ruthless calculus. According to Weeks, King's only crime was making a fist in Bulger's presence during an argument at Triple O's, a bar that had become Bulger's headquarters. "A week later, Tommy was dead." King made the fatal mistake of getting into a car with Bulger, Flemmi, and John Martorano.
That same night, Bulger killed another man named Buddy Leonard and left his body in Tommy King's car—a deliberate act of misdirection to confuse investigators.
The Race-Fixing Years
In 1974, Bulger formed his most consequential partnership. Stephen Flemmi became his co-leader, and together they served as enforcers for the Winter Hill Gang.
That same decade, the gang partnered with Anthony "Fat Tony" Ciulla in an elaborate horse race-fixing scheme. The operation was sophisticated: they bribed jockeys, threatened trainers, and drugged horses to predetermine race outcomes across the entire East Coast.
Bulger and Flemmi's specific role was placing bets with bookmakers around the country—collecting the guaranteed payoffs that came from knowing which horse would win before the race was run.
The scheme generated enormous profits. But Bulger had other interests too—including some that were distinctly political.
Firebombs and Desegregation
In the mid-1970s, Boston was tearing itself apart over school desegregation. Federal Judge Wendell Arthur Garrity had ordered the city to integrate its schools through busing—transporting Black students to predominantly white schools and vice versa. South Boston, fiercely protective of its Irish identity, erupted in protest.
Bulger took action.
In late summer of 1974, he and an accomplice reportedly set fire to an elementary school in Wellesley—an attempt to intimidate Judge Garrity himself. A year later, on September 8, 1975, Bulger threw a Molotov cocktail into the John F. Kennedy birthplace in Brookline.
Why attack JFK's birthplace? Because Senator Ted Kennedy—JFK's brother—had vocally supported Boston school desegregation. Bulger used black spray paint to scrawl his message on the sidewalk outside the national historic site: "Bus Teddy."
The man who would later claim to prey only on criminals had firebombed a school and a national landmark over a political dispute.
The FBI Comes Calling
In 1971, the FBI made its first approach. They wanted Bulger as an informant, hoping he could provide intelligence on the Patriarca crime family—the Italian Mafia that controlled organized crime throughout New England.
The bureau assigned John "Zip" Connolly to make the pitch. Connolly had grown up in Bulger's neighborhood—a Southie kid who'd gone straight and joined the FBI. The bureau thought this connection would help.
It didn't work. Bulger refused to cooperate.
What Bulger didn't know was that his new partner, Stephen Flemmi, had been an FBI informant since 1965—practically the beginning of his criminal career. For nearly a decade, Flemmi had been feeding information to the bureau while committing murders alongside Bulger.
The Devil's Bargain
Exactly how Bulger became an informant remains disputed. Connolly loved telling the story: a late-night meeting at Wollaston Beach, the two men sitting in his agency car. Connolly allegedly explained that the FBI could help Bulger in his ongoing feud with the Patriarca family's influential underboss, Gennaro "Jerry" Angiulo.
Bulger supposedly responded: "Alright, if they want to play checkers, we'll play chess. Fuck 'em."
Others believe Flemmi betrayed Bulger to the FBI—that the bureau threatened to cut Flemmi loose unless he delivered his partner. Once the FBI had leverage over Bulger, he had little choice but to cooperate.
Either way, by 1975, both men were on the FBI's payroll.
In a 2011 interview, Flemmi summarized the arrangement with brutal honesty: "Me and Whitey gave the Feds shit, and they gave us gold."
How the Deal Worked
On paper, Bulger and Flemmi were informants providing intelligence about the Italian Mafia. In practice, the relationship was far more corrupt.
Kevin Weeks later met with Connolly and was shown a photocopy of Bulger's FBI file. Connolly claimed that ninety percent of the information came from Flemmi, but he had to put Bulger's name on the files to keep Bulger listed as an "active informant."
Why did this matter? Because as long as Bulger was active, Connolly could justify meeting with him—and feeding him "valuable information" in return.
This wasn't a one-way flow of intelligence. It was an exchange. Bulger gave the FBI information about Italian mobsters. The FBI, through Connolly, gave Bulger warnings about investigations, names of potential witnesses, and intelligence about rival criminals.
Weeks discovered something else when he reviewed those files: the information wasn't just about Italians. "There were more and more names of Polish and Irish guys, of people we had done business with, of friends of mine." Many of these people had later been arrested for crimes mentioned in the reports.
Connolly had assured Weeks that the files were never disseminated—that they were for his "personal use" only. This was a lie. When supervisors asked to see them, Connolly had to comply. The information Bulger provided led to arrests of people who thought they were Bulger's allies.
The Bureau's Priorities
How did the FBI justify protecting murderers?
During the 1970s and 1980s, the bureau's Organized Crime Program had one overriding priority: dismantling the Italian-American Mafia. They considered La Cosa Nostra a greater threat than all other organized crime groups combined.
The Winter Hill Gang was Irish. The Patriarca family was Italian. In the FBI's worldview, using Irish criminals to destroy Italian criminals was simply good strategy.
This framework allowed agents like Connolly to look the other way while Bulger and Flemmi murdered rivals, shook down legitimate businesses, and flooded Boston's streets with drugs. As long as they kept delivering intelligence on the Italians, they were useful.
The FBI knew about the Winter Hill Gang. They chose to ignore it.
The Body Count
While under FBI protection, Bulger continued killing. The exact number of his victims remains disputed, but prosecutors would eventually try him for involvement in nineteen murders.
His methods were efficient. He would lure victims into cars or meetings, execute them quickly, and dispose of the bodies carefully. Many of his victims were fellow criminals—bookmakers who'd cheated him, rivals who'd disrespected him, potential witnesses who knew too much.
But not all. Some were simply in the wrong place at the wrong time. Some were killed to send messages. Some were killed because Bulger suspected them of being informants—a stunning hypocrisy from a man who was himself feeding information to the FBI.
The Protection Unravels
The arrangement lasted nearly two decades. Then, in December 1994, everything fell apart.
John Connolly, who had retired from the FBI but maintained contact with Bulger, learned that federal prosecutors were preparing a RICO indictment. RICO—the Racketeer Influenced and Corrupt Organizations Act—was the same weapon the FBI had used to devastating effect against the Italian Mafia. Now it was being turned on Bulger.
Connolly warned him.
On December 23, 1994, Bulger vanished.
Sixteen Years Underground
Bulger fled Boston with Catherine Greig, his longtime girlfriend. They would remain fugitives for sixteen years—one of the longest manhunts in FBI history.
Five years after his disappearance, Bulger was added to the FBI's Ten Most Wanted Fugitives list. Only Osama bin Laden was considered more wanted.
But unlike bin Laden, who hid in fortified compounds in remote Pakistan, Bulger lived in plain sight. He and Greig rented a modest apartment in Santa Monica, California—one of America's most desirable beach communities, walking distance from the Pacific Ocean.
They paid cash. They kept to themselves. They adopted assumed names. And somehow, despite the FBI's supposedly intensive search, nobody found them for over a decade.
The Arrest
The end came in June 2011. Acting on a tip, FBI agents arrested Bulger and Greig outside their Santa Monica apartment. He was eighty-one years old.
Inside the apartment, agents found over $800,000 in cash hidden in the walls, along with an arsenal of weapons. Bulger had been prepared to run again—or fight.
He and Greig were extradited to Boston under heavy guard. The city that had spawned him would finally hold him accountable.
The Trial
Bulger's trial began in June 2013. He faced thirty-two counts: racketeering, money laundering, extortion, weapons charges, and complicity in nineteen murders.
The prosecution's case relied heavily on testimony from former associates—men like Kevin Weeks who had once been loyal soldiers but had flipped to save themselves. They described murder after murder, each one painting Bulger as the calculating architect of violence.
Bulger denied ever being an informant—adamantly, repeatedly, publicly. This was the one charge that seemed to genuinely anger him. He could apparently accept being called a murderer. Being called a rat was intolerable.
The FBI's own records proved otherwise. Documentation showed he had been providing information since 1975.
On August 12, 2013, the jury returned its verdict: guilty on thirty-one of thirty-two counts, including both racketeering charges. They found he had been involved in eleven of the nineteen murders.
On November 14, U.S. District Court Judge Denise Casper sentenced him to two consecutive life terms plus five years.
Catherine Greig, who had helped hide him for sixteen years, received eight years for conspiracy to harbor a fugitive and identity fraud.
A Violent End
Bulger was sent to United States Penitentiary Coleman II in Florida—a high-security facility. He was eighty-four years old and in declining health, confined to a wheelchair.
In October 2018, the Bureau of Prisons transferred him. First to the Federal Transfer Center in Oklahoma, then to United States Penitentiary Hazelton, near Bruceton Mills, West Virginia.
Within hours of his arrival at Hazelton, inmates beat Whitey Bulger to death. He was eighty-nine years old.
The killing appeared planned. In 2022, prosecutors charged three men with conspiracy to commit first-degree murder: Fotios Geas, Paul DeCologero, and Sean McKinnon. Geas and DeCologero were allegedly connected to the Mafia—the same organization Bulger had spent decades informing against.
The man who had escaped justice for so long met his end in the most fitting way possible: killed by the kind of men he'd spent his life betraying.
The Corruption Exposed
Beginning in 1997, press reports started exposing the full scope of the FBI's complicity. The Boston Globe and other outlets documented case after case of criminal misconduct by federal, state, and local officials tied to Bulger.
John Connolly, the agent who had recruited and protected Bulger for years, was convicted of racketeering in 2002 and second-degree murder in 2008. He remains in prison.
The scandal was one of the most embarrassing in FBI history. Agents had protected a serial killer for decades, allowing him to murder rivals while feeding the bureau information about the Italian Mafia. The bureau's single-minded focus on destroying La Cosa Nostra had blinded them to the monster they'd created.
Or perhaps they hadn't been blind at all. Perhaps they'd simply decided that some murders mattered less than others.
The Legacy
What does Whitey Bulger's story tell us?
It tells us that law enforcement agencies can become so focused on one target that they ignore crimes by their own assets. It tells us that informant relationships, once established, can corrupt the agents who manage them. It tells us that a man can be simultaneously a government cooperator and a prolific murderer—and that the government will look the other way as long as he's useful.
Bulger himself claimed to have operated by a code: prey on criminals, not civilians. This was self-serving mythology. He killed whoever needed killing. He trafficked drugs that devastated communities. He corrupted public officials at every level.
His brother William, the respected politician, maintained until the end that he'd had no knowledge of Whitey's crimes. Perhaps that's true. Or perhaps the two brothers from the housing projects in Southie understood each other better than either ever admitted.
In the end, Whitey Bulger was exactly what the FBI accused the Italian Mafia of being: a violent, corrupt, ruthless criminal organization. The only difference was that he had government protection.
Until he didn't.