NEW YORK — James "Whitey" Bulger, arrested Tuesday after 16 years on the lam, ruled over Boston for decades as a mythically untouchable crime boss.
As leader of the feared Winter Hill Gang, Bulger reaped untold millions through theft, extortion, racketeering, drug trafficking and murder, federal indictments charge. And when federal prosecutors closed in on him in 1994, he skipped town just days before a warrant was issued for his arrest.
He owed it all to help from the F.B.I.
It is an oft-told tale: in the mid-1970s, the F.B.I.'s organized crime office in Boston recruited Bulger, already a fixture in the city's Irish mob, to serve as a high-level confidential informant. For the next 20 years, he secretly fed the bureau information about his counterparts in the Italian Mafia, tips that contributed directly to the dismantling of some of the country's most powerful crime families.
In return, the F.B.I. shielded Bulger and his associates from prosecution, using methods that regularly veered into the brazenly illegal.
Wiretaps and listening devices from other law enforcement agencies were exposed. Government informants were identified — then allegedly rubbed out by Bulger and his cohorts. Innocent men were allowed to be framed for murders committed by Bulger's gang and died in prison.
Many elements of Bulger's unholy alliance with the F.B.I. have been chronicled through the testimony of his fellow gangsters and through civil lawsuits brought against the federal government by family members of his victims.
His F.B.I. handler, John J. Connolly Jr. — who allegedly tipped Bulger in 1994 of the pending federal indictment, prompting his 16-year flight from the law — sits in prison with a 40-year sentence, convicted of racketeering and murder. Connolly's supervisor, John Morris, pled guilty to accepting bribes from Bulger in exchange for inside information and in 1995, he resigned from the bureau in disgrace.
Yet other secrets have gone unrevealed, and some believe Bulger, 81, charged with a litany of crimes, including 19 murders, has the power to expose a wide range of undisclosed official corruption from one of the darkest eras in federal law enforcement.
"Somebody warned him about bugs. Somebody warned him about wiretaps. Somebody warned him about informants and he murdered them," said Austin McGuigan, a Connecticut prosecutor who investigated Bulger in the 1970s and 1980s. "Who was it? I don't know."
"Bulger can confirm things that haven't been confirmed yet," he said.
A prolonged trial may also open the F.B.I. to new scrutiny over how much the bureau's leadership at the time knew about Bulger's relationship with Connolly and other corrupt agents.
Connolly, who is appealing his 2005 murder conviction, calls himself a "fall guy," claiming that his protection of Bulger was sanctioned at the highest level of the bureau.
"It's the worst cover-up in the modern annals of the Justice Department," he told the Los Angeles Times in May.
Robert Stutman, who investigated Bulger as head of the Drug Enforcement Agency's Boston office in the late 1970s and 1980s, said Connolly's claims of innocence were absurd.
"I think John Connolly is where he deserves to be," he said. "He's a scumbag."
Yet he agreed there may be merit to Connolly's claim that higher-ups at the bureau knew of and sanctioned Bulger's activities.
"He may be the fall guy for somebody in headquarters," he said. "It's hard for me to believe that all this happened without people above knowing something."
William Christie, a New Hampshire attorney, brought suit against the F.B.I. on behalf of the family of a victim of Bulger's gang, winning a multi-million judgment against the bureau that was later overturned on technical grounds.
He said evidence uncovered during the civil trial clearly demonstrated that F.B.I. leadership was aware that Bulger was being protected from prosecution and receiving tips about pending investigations against him.
Christie cited a memo written within F.B.I. headquarters in the early 1980s detailing allegations by agents from the Miami and Tulsa field offices that agents in the Boston office were deliberately sabotaging murder investigations related to Bulger.
"There was clear knowledge that Connolly's supervisors and F.B.I. headquarters were aware of allegations that Connolly was leaking confidential information to Bulger," he said. "I don't think that's debatable."
Damon Katz, chief division counsel for FBI's Boston division, declined to comment on the allegations. "That's not something we're going to discuss," he said.
As for Bulger -- facing extradition to Boston on Friday -- what information he chooses to share, if any, remains to be seen. But many people will be listening carefully.
"This sort of opens up the box again," said James E. McDonald, a Miami attorney representing John Connolly in his appeal. "If he talks, it could be very interesting. He could say a lot."