Whitey Bulger is a heinous man. The notorious South Boston mobster (allegedly) beat people to death with bats, stabbed them, shot them, strangled them, and pulled out their teeth so that, in the days before DNA, they couldn’t be identified. He encouraged the perception among Southie residents in the '70s and '80s of neighborhood protector, but in actuality Whitey flooded the streets with heroin and crack, enough not only to ruin families but very nearly Southie itself. Depending on the account, Whitey heard of criminal charges being brought against him in either December 1994 or January 1995. He fled town, and, after Osama bin Laden’s death, became the most-wanted man in America. Wednesday, working off a tip, federal agents arrested him outside a Santa Monica, California, apartment, where he had been living with his longtime girlfriend, Catherine Greig.
That’s the simple narrative: he was an evil man who escaped justice, until now. The more complex one is that Boston needed Bulger—and, more specifically, that the FBI did. The Boston office in the '70s and '80s wanted to wipe out the Italian mafia. To do it, the FBI enlisted the help of sundry characters, none worse than Whitey, the leader of the mostly Irish Winter Hill gang. The agreement between the two, as spelled out in, among other places, Black Mass, the definitive book on Bulger and the FBI, called for Bulger to give the agency dirt on the Italian mob’s goings-on in exchange for, well, Bulger's containing himself to low-level criminal acts: loan sharking and the like. The idea was that Whitey wouldn’t kill anybody.
But Whitey did kill people (allegedly). He would later be charged with 19 murders, with potential involvement in 20 more, and up to 11 of them carried out while he cooperated with the FBI. Some of the victims—girlfriends or businessmen—didn't have ties to the underworld. The bureau was more than a complicit bystander in all this. Whitey corrupted FBI agents. One of his longtime lieutenants, Kevin Weeks, once told Boston magazine that Whitey could call on six FBI agents at any hour “who would willingly hop in the car with a machine gun.” Another law-enforcement type told the magazine that during the '70s and '80s at least 10 FBI agents were corrupt. Whitey used to wake up in the morning, gaze out his window, and say, “I own this town.”
Arguably no agent was worse than John Connolly, Whitey’s handler within the FBI. Prosecutors later said that Connolly was the one who tipped off Whitey of his coming arrest in 1994. Connolly was convicted in 2002 of racketeering and in 2008 of second-degree murder for his part in helping Whitey evade capture.
By then, the strange thing was that the FBI’s plan worked: the bureau had diminished the Italian mafia to the state of a bad joke. Of course, that’s all the Boston office was, too. The corruption was so well known it was romanticized: The Departed is based on the saga of Whitey and the FBI. Connolly took the biggest fall for the bureau. Today, many if not all of the agents presumed to be owned by Whitey are either retired or dead, many of them having left the FBI without repercussions. Connolly has long argued that his supervisors, hell, even the lawyers in the U.S. Attorney’s office, knew who his informant was. He has turned his prison sentences into martyrdom, and not without cause. Perhaps as a result, the FBI and U.S. Attorney’s office have prosecuted cases with unprecedented zeal, the most notorious of which is the low-ranking Boston city councilor given a federal sentence for a petty bribe taken in a poor, black neighborhood. Whitey presides over all these cases, smiling, and still on the lam. His capture Wednesday means history is writing the last pages of the worst chapter of Boston’s law-enforcement history.
Whitey’s capture means history is writing the last pages of the worst chapter of Boston’s law-enforcement history.
But it also means the writing of perhaps the last defining chapter of Boston. Boston’s tribalism, its inward focus—some might even call it its solipsism—used to nonetheless attract international fascination. But the nation is hardly puritanical anymore, the Transcendentalists have been dead for more than 100 years, the Kennedys are out of power, and now Whitey is behind bars. The city will forever remain an embodiment to its history. But with Whitey’s arrest, that history is no longer living, vital. His capture is a good thing, in fact the very best thing. But there’s a reason some in Southie told the Boston Globe this morning “[t]here are a lot of people who would still defend him in this neighborhood.” He was the city’s link to a grander narrative.