But few lawmen — with the notable exception of John Connolly, his longtime handler at the F.B.I. — were ever convicted of corruption.
Now that he is back in custody after his capture last week in Santa Monica, Calif., the looming question is whether Mr. Bulger, a longtime informant — who fed information about his rivals to the F.B.I. for years in return for their protection — will squeal again.
“I think there are a whole bunch of people out there he could probably name who are probably a little puckered right now, who are worried what he might say,” said Robert Fitzpatrick, who was an assistant special agent in charge of the Boston office of the F.B.I. in the 1980s, and who has testified that he tried unsuccessfully to end Mr. Bulger’s run as an informant.
The Bulger saga has been explored in trials, Congressional hearings, reams of newsprint and a shelf of books. But a review in recent days of hundreds of pages of trial transcripts and court decisions, along with interviews with several former law-enforcement officials and lawyers connected with the case, shows that, despite all the scrutiny, there has never been a full official reckoning of the public corruption that allowed Mr. Bulger to thrive for so long.
His partners have testified that former F.B.I. agents were on the take, and named names, but in many cases, the agents simply denied it and nothing happened. A report promised years ago by a special prosecutor was never issued. It is unclear even now whether the government wants to reopen old wounds.
“It’s not always just the guy pulling the trigger who is guilty,” said Tom Foley, a retired state police commander who pursued Mr. Bulger with Ahab-like intensity for years, only to see him elude capture thanks to help from his F.B.I. friends. “It’s also the people who set that up and allowed it to happen, and especially the people who had a responsibility to put a stop to it.”
Even if Mr. Bulger, 81, decides to talk, it is not clear that he has much to bargain with: he stands accused of 19 murders, and some of his closest associates have implicated him. The statute of limitations has passed for most crimes he could talk about, and most former investigators are retired or dead. But former F.B.I. agents and lawyers connected to the case say that Mr. Bulger may decide that he wants to settle a few scores.
For much of the 1980s, he turned the world of Boston law enforcement upside down.
The F.B.I. considered Mr. Bulger and his partner Stephen (the Rifleman) Flemmi “top echelon” informants, but the pair seemed to get more from the bureau than they gave. Federal agents helped them by locking up rivals, protected them from other investigators and tipped them off when witnesses threatened to implicate them. Those would-be witnesses quickly wound up dead, sometimes with their teeth removed to make it harder to identify the corpses.
In those days it was not just the G-men who referred to the gangsters with colorful nicknames like Whitey and the Rifleman. Mr. Bulger had his own nicknames for the F.B.I. agents he wined and dined and used, associates testified: Zip, Agent Orange, The Pipe, Doc, and Vino.
John (Zip) Connolly was the F.B.I. agent who handled both Mr. Bulger and Mr. Flemmi, using their information to build high-profile cases against the Mafia. Mr. Bulger called him “Zip” because they came from the same South Boston housing project and had shared a zip code. But Mr. Connolly grew too close to his source. He was convicted of racketeering and obstruction of justice in 2002, in part for tipping Mr. Bulger off in 1994 when he was finally about to be indicted. Then he was convicted of second-degree murder in 2008 for warning Mr. Bulger in 1982 that a man named John Callahan was likely to implicate him in several murders connected with an attempt to profit from World Jai Alai, a company with fronts in Connecticut and Florida. Mr. Callahan’s body was found in the trunk of a car at Miami International Airport, after an attendant noticed blood dripping from it.
A lawyer for Mr. Connolly, James E. McDonald, said that Mr. Bulger’s capture could stir things up. “If I were the Department of Justice prosecutors, I’d be nervous, because if Bulger starts to talk, the whole edifice they have created about John being the corrupt agent will have holes you could drive a truck through,” he said.
Mr. Connolly did not act alone.
His supervisor at the F.B.I., John (Vino) Morris, admitted to taking $7,000 in bribes from Mr. Bulger and Mr. Flemmi — beginning when he asked them to pay for his mistress to fly to a training session he was attending in Georgia. Mr. Bulger and Mr. Flemmi took to calling him “Vino” after a 1981 dinner at Boston’s Hotel Colonnade, where he drank a great deal of wine. They later sent him a case, with $1,000 in it. But Mr. Morris was granted immunity when he agreed to cooperate with the government.
Still, he may have the most to fear.
Mr. Morris admitted that in 1988 he told The Boston Globe, which has long done ground-breaking reporting on the Bulger saga, that Mr. Bulger was an F.B.I. informant. His lawyer, Michael A. Collora, said that Mr. Morris did so in the hopes that exposing the troubled relationship would end it. But Mr. Bulger’s brother, William M. Bulger, a former president of the Massachusetts State Senate, saw a more sinister motive. He testified before Congress in 2003 that the leak’s purpose was “bringing about the death of James Bulger."
After Whitey Bulger became a fugitive, he called Mr. Morris with a threat: he vowed to take Mr. Morris with him if he went down.
But Mr. Collora noted in an interview this week that Mr. Morris, who he said worked part-time at a wine store, had already admitted wrongdoing and had been granted immunity. The statute of limitations has run its course for most crimes, he said, and there are serious questions about what kind of witness Mr. Bulger would make. “A situation where you have a man who’s been on the lam for 16 years, who says now I’ll help you out, even though he’s done 19 murders?” he asked.
One memo that has received little scrutiny shows how officials in Washington were warned that the F.B.I.’s Boston office was too close to Mr. Bulger. It was written in 1982, after the Jai Alai murders were linked to Mr. Bulger’s group, which was known as the Winter Hill gang. An agent in the Miami office warned officials in Washington that local investigators were cutting the F.B.I. out of the loop, in part because they believed “that some agents in the Boston F.B.I. would not pursue allegations against the Winter Hill gang vigorously.” Sean M. McWeeney, who was in charge of the bureau’s organized crime section, wrote that he held meetings in Washington and Tulsa to reassure the local investigators.
It took two decades for the full story to get out — including Mr. Connolly’s role in the murders.
John McIntyre was another witness who never made it to the stand. Mr. McIntyre, a 32-year-old fisherman who agreed to cooperate with investigators in 1984 about Mr. Bulger’s involvement in drug and gun shipments. Tipped that there was an informer in their midst, Mr. Bulger and Mr. Flemmi chained Mr. McIntyre to a chair and made him confess. They then tried to strangle him with a rope, and when that did not work, Mr. Flemmi testified, they shot him and removed his teeth.
A federal judge awarded Mr. McIntyre’s estate $3.1 million, finding that the federal government was liable for his death because Mr. Connolly had leaked Mr. Bulger and Mr. Flemmi enough information for them to identify him as an informer. Steven Gordon, the Concord, N.H., lawyer who represented the estate, said that the government’s defense showed a continued refusal to come clean. “They allowed a whole city to come under siege,” he said.
When Mr. Bulger fled, some joked that he should be on the F.B.I.’s “least wanted” list. In a 1999 ruling after hearings that helped expose the F.B.I.’s dealings with Mr. Bulger, Federal District Court Judge Mark L. Wolf cited evidence that “raises questions concerning whether the F.B.I. has consistently made its best efforts to apprehend” him. He noted that agents had waited 15 months before approaching Theresa Stanley, the first girlfriend Mr. Bulger fled with, who returned to Boston in 1995 because she disliked life on the road.
Judge Wolf began his decision with a quote from Lord Acton, who wrote in 1861 that "everything secret degenerates, even the administration of justice."
“This case,” the judge wrote, “demonstrates that he was right.”