For well over a decade, Whitey Bulger was America’s most wanted gangster—the FBI’s biggest domestic target, second in priority only to Osama bin Laden. As a leader of Boston’s Winter Hill Gang, Bulger was wanted by the bureau on 19 charges of murder, as well as for numerous other offenses including racketeering, extortion and narcotics distribution. And yet, for 16 years—from just before Christmas 1994 until June 2011—he remained at large.
“This was a long hunt, and it had a lot of ups and downs,” Dave Wedge, co author (along with Casey Sherman) of Hunting Whitey: The Inside Story of the Capture & Killing of America’s Most Wanted Crime Boss tells A&E True Crime. “All over the world. They were chasing ghosts. But he never left the country. He was hiding in plain sight.”
Whitey Bulger’s Inside Man
The main reason Bulger was able to first evade capture was that he had a man on the inside: FBI agent John Connolly, who came from the same South Boston housing project. Connolly and Bulger had a deal: For more than 15 years, Bulger served as an FBI informant, providing Connolly and others in the bureau with information on rival gangs—including the Italian mafia. In exchange, he received the bureau’s protection from other arms of law enforcement.
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In 1994, Connolly tipped Bulger off to a secret grand jury indictment, allowing the mobster to flee before his arrest. That double-cross became public when Connolly himself was arrested, tried and convicted for his conduct. Connolly’s boss, John Morris, was also implicated, he but received immunity for his testimony.
Rich Teahan, a retired FBI agent who worked on the Whitey Bulger case from 2006 onward and served as the Bulger Fugitive Task Force coordinator, says the team that ultimately brought Bulger down was motivated by Connolly’s betrayal.
“We were stained by that, but also kind of energized by it,” Teahan tells A&E True Crime. “So much had occurred which had embarrassed the FBI, which stained our reputation in Boston and stained the relationships [between] law enforcement [and the public]. And we just wanted to right that wrong.”
Bulger’s Women
When Bulger first fled Boston, he left with Teresa Stanley—his longtime girlfriend whom he’d been dating since the late 1960s. They spent New Year’s in New Orleans, then traveled to Arizona and California—but they went back to Boston in 1995 at Stanley’s behest. She had family in Boston that she couldn’t live without, so Bulger dropped her in a Chili’s parking lot and then picked up another woman—his mistress, Catherine Greig, whom he’d also been seeing nearly the entire duration of his relationship to Stanley.
Greig and Bulger remained together on the lam until their arrest 16 years later.
“There was a true love there,” Wedge says, adding that with a nearly 20-year age difference between them, Greig became a caretaker for Bulger. She did grocery shopping and other errands, such as crossing the border to Mexico to buy the aging gangster his heart medication.
There are no public indications that Greig regretted going on the run, Wedge says, noting that she never cooperated with authorities after her arrest.
“Everyone that spoke to us said that they were a very kind, loving couple,” Wedge say, adding that Greig made regular calls back home to her twin sister Margaret, during which time she would sing her partner’s praises.
“She said that Catherine always spoke lovingly about Jim—they called him Jim. They never called him Whitey.”
Fake IDs and Laundered Money
Bulger and Greig drove across the country, stopping numerous times before settling in Santa Monica, California.
Money wasn’t scarce—Bulger’s net worth was estimated at around $50 million before he fled. And while it’s unknown how much of his fortune Bulger had access to, at the time of his arrest in 2011 investigators found $822,000 in cash in the walls of his Santa Monica apartment. Still other money was recovered from safety deposit boxes in Montreal, Dublin, London and Clearwater, Florida.
But Bulger was cautious with how he spent his money, Teahan says, out of fear that the cash could be traced. The nest egg consisted almost exclusively of $100 bills dated to 1995, and after Bulger’s arrest, Teahan says the mobster confided that he was worried his outdated large bills might draw suspicion, so he’d regularly take loads of cash to Las Vegas. There, he’d trade the cash at the major casinos for playing chips, then would gamble a few hands before cashing out his chips for new, untraceable money.
Bulger also secured a fake ID for himself by striking up a friendship with James Lawler, a homeless man in Santa Monica who was approximately Bulger’s age and looked similar.
In return for Lawler’s birth certificate and other identifying documents, Bulger paid the man a few hundred dollars and rented him an apartment in West Los Angeles.
“He was that fluent in his methods—thinking of those things,” says Teahan. “He had a very high IQ.”
Asked if he respected Bulger, Teahan says, “I have no respect for what he did. What I have respect for—in an adversarial way—is how he was as a fugitive.”
Near Misses
Bulger was nearly caught several times—perhaps never more colorfully than in 2006 in San Diego, where he went to a movie theater to watch The Departed, a Martin Scorsese film based on Bulger’s life.
An off-duty sheriff’s deputy originally from Boston saw Bulger in the cinema, sitting a few rows away.
“When Bulger came out, they looked each other in the eye,” Wedge says. At that, Bulger got on a trolley and took off. The deputy—who was unarmed—went back to the courthouse for a firearm, but by then Bulger was long gone. The law enforcement agent went to a nearby precinct to report the sighting, but the tip hit a dead end.
“Stranger than fiction,” says Wedge.
There were also suspected Bulger sightings that were overly investigated, where Teahan or other agents would fly internationally on a tip that he was in Cuba, Italy or in Guadalajara, Mexico.
“They’d be dead ends,” Teahan says. “Sometimes the energy just gets sapped out of you because you’d be thinking, ‘This [lead] is a good one, this is a good one,’ and then you’d be exhausted because it wasn’t. And there were thousands of those.”
The Final Capture
Eventually, Bulger’s luck ran out—but only after the FBI turned its attention to Bulger’s accomplice, Greig. The bureau knew the moll had regularly gotten dental work and plastic surgery in the years prior to the couple’s escape from Boston, so they contacted and took out advertisements with plastic surgery and dental trade magazines asking for tips to find her.
That scored them new photographs of Greig, which had been taken at one of her plastic surgeon’s offices. They then aired those photographs on TV ads across the country, loudly advertising the $2 million reward.
Within a day of those ads running, a former neighbor called to report the fugitive couple’s Santa Monica address. The next morning, on June 22, 2011, Bulger was arrested in the building’s parking garage, after being lured out under false pretenses by the building manager.
Teahan was working at home at the time of Bulger’s arrest and got news of it via a text message from a fellow agent.
“I was sitting in a chair, and I threw my phone across the room. And I just jumped for joy.”
The former mob boss, reviled by many in Boston’s underworld as a snitch, was killed in prison seven years later, on October 20, 2018. Bulger, who was serving two life terms plus five years for his crimes, is believed to have been bludgeoned to death by two inmates using a padlock inside of a sock as their main weapon. The FBI is still investigating the murder, but no one has been charged.
For her role in helping Bulger evade authorities all those years, Grieg was sentenced to eight years in prison and an additional 21 months for refusing to testify before grand juries. On July 21, 2020, Grieg completed her prison sentence after having spent the last year under home confinement.
[UPDATE: On August 18, 2022, three men were charged with murdering Bulger: Fotios Geas, Paul J. DeCologero and Sean McKinnon, all of whom were in prison with Bulger, were charged with conspiracy to commit first-degree murder. It’s unclear why it took four years for the men to be charged in the case, given they were quickly identified as suspects.]
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