Whitey Bulger, Vicious Ruler of a Long-Gone Boston, Sentenced to Life

The former FBI informant and Irish mob boss was sentenced to two life terms and ordered to pay $19.5 million in restitution

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U.S. Attorney's Office / AP

This 1980 black and white surveillance photo shows Bulger, right, with another man at a Lancaster Street garage in Boston's North End.

A dinosaur in an orange jumpsuit shuffled into a federal courthouse in Boston Wednesday. He sat at a table and stared blankly as a parade of men and women stood and hurled bitter invectives at him. They called him evil, a punk, a sociopath, a piece of trash, a coward, a miserable human, a disgrace to the Irish, a devil, a rat, a man for whom the electric chair would be too good. James “Whitey” Bulger, the onetime head of Boston’s Irish mob, offered no response.

This is how it ends for Bulger, the man who was once the most feared criminal in Boston, and who became the most-wanted fugitive in America: sitting in a courtroom in a city he no longer recognizes, awash in the anger and tears of his victims’ family members, resigned to the inevitability that the same Justice Department that once enabled his decades-long crime spree will now lock him up for the rest of his life.

The sentence in Bulger’s federal racketeering case came down Thursday morning. It will send the 84-year old convict to prison for the rest of his life–two life terms plus five years–and order him to pay $19.5 million in restitution.

(MORE: Families of Whitey Bulger’s Victims Speak Out Before Sentencing)

At this point, though, it’s almost beside the point, both for the geriatric gangster and the city he once lorded over. In ways both big and small, Boston left Whitey Bulger behind long ago. Young college graduates have taken over wide sections of the blue collar neighborhoods Bulger once terrorized. Bulger knew the section of town he stood trial in as a post-industrial waterfront wasteland of rotting piers and empty parking lots; now, it’s the site of a historic building boom. Boston just elected its first new mayor in 20 years, replacing a retiring machine boss who ran the town at a time when Bulger seemed untouchable. As a fugitive, Bulger had fled Boston, but it’s the city itself that has put distance between itself and Whitey Bulger.

Bulger once ruled over wide swaths of Boston. From deep inside South Boston, the city’s clannish blue-collar Irish neighborhood, Bulger’s gang oversaw a network of loan sharks and gambling rackets. He killed and stole and protected the drug dealers who devastated his neighborhood. He did it all with the protection of the Boston FBI, which used Bulger and his partner, Stephen “The Rifleman” Flemmi, as informants against the city’s mafia. FBI policy shielded Bulger and Flemmi from prosecution. Agents in Bulger’s orbit repeatedly tipped the gangster off about criminals who came to the FBI to inform against him; this practice continued, even after those would-be informants began turning up dead.

From the mid-1970s until the mid-1990s, Bulger’s gang was untouchable. And when the federal indictments did finally come down, in 1995, Bulger had a head start. His former FBI handler (now doing a 40-year prison stretch in Florida for a Bulger-related murder) tipped off Bulger about the pending indictments, sending the gangster on what would become a 16-year run as a fugitive. It was only after Bulger fled Boston, at a series of federal court hearings, that Bulger and Flemmi were exposed as government informants and murderers. Federal agents caught up with Bulger and his girlfriend, Catherine Greig, living in a rent-controlled Santa Monica apartment in 2011; by that time, the other members of the Bulger gang had long since struck plea deals with the US Attorney’s office. Several have written books and become true crime celebrities; only a few remain in prison.

(WATCHA Mysterious Death of Witness for ‘Whitey’ Bulger Trial)

In August, a jury found Bulger guilty of 31 charges spanning murder, money laundering, racketeering, and weapons violations. But for those closest to it, Bulger’s trial was deeply unsatisfying. A jury could only agree with 11 of 19 murder charges prosecutors presented them with. The verdict confirmed what the city already knew about Bulger — that he was a thief and a killer. But it didn’t come close to painting a full picture of Bulger’s reign, in which the gangster and the local FBI office amplified and profited from each other’s corruption.

When Bulger was an FBI informant, his handlers covered up his crimes because they feared losing the wiretap warrants at the center of a case that wound up crippling the Boston mafia. The objectives were equally as narrow at trial. To pile on evidence against Bulger, prosecutors were forced to minimize the role of the government that enabled his crimes. This was a criminal trial, not a truth commission. Fear of muddling their evidence kept prosecutors from dwelling on the fuller picture of the corrupt Bulger-FBI relationship. And in doing so, they obscured both what really happened during Bulger’s two-decade crime spree, and why it matters.

Bulger didn’t just kill. He killed with government protection. But it wasn’t until Wednesday, when the parade of victims’ family members addressed Bulger, that someone other than Bulger’s lawyers widened the circle of blame. David Wheeler, the son of a Tulsa, Oklahoma, businessman Bulger had murdered, called Bulger’s relationship with federal law enforcement officers “even more grotesque” and “more horrifying” than his father’s death. “The FBI is responsible for my father’s murder,” Wheeler said. “They are as responsible as the defendant sitting before you.”

More than anything, though, Bulger’s trial made the man who once ran Boston look like a fossil, an anachronism. Boston has grown tremendously in the nearly two decades since Bulger fled town. In pushing the gangster in and out of a courtroom every day, the city charted its evolution beyond its former existenceas a living, breathing Scorsese film set.

For one, the fear and the code of silence that Bulger once inspired have disappeared. That shone through as Wheeler called Bulger a “pile of jailhouse rags,” and as Steve Davis, whose sister had been murdered by Bulger and Flemmi, told Bulger he’d like to strangle him.

Physically, too, Bulger’s Boston has vanished. Triple O’s, the bucket-of-blood South Boston barroom where Bulger once held court, has become a sushi restaurant surrounded by luxury condominiums. Bulger stood trial in a South Boston courthouse, just down the street from the scene of one of his gruesome double-murders.

The courthouse didn’t exist when he ruled; the whole neighborhood consisted of weed-choked waterfront parking lots, fishing piers, and dive bars. Those parking lots, where kids once played street hockey, and where Bulger once stalked his victims, have vanished, replaced by office towers and luxury apartments. A sparkling headquarters for a biotech firm is rising next to the federal courthouse. Across the street, next door to a chapel for departing fishermen, there’s a new social hall for tech workers.

Boston is a young, prosperous, growing city. It’s not the parochial town Bulger left. It’s a city where, as Wheeler said to Bulger Wednesday, “You don’t even matter anymore.”

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