When a young, skinny kid named John Connolly visits a South Boston drugstore with his friends in the summer of 1948, he finds local teenage legend Jimmy Bulger—who has already been nicknamed “Whitey” by the cops because of his striking blond hair—manning the counter. Bulger, known for his daring—and illegal—activities, offers Connolly and his friends free ice cream cones, but Connolly has been warned by his mother not to take food from strangers. Bulger protests that they’re not strangers because they’re both from Irish families. Connolly, starstruck, accepts a vanilla cone.
In an introduction dated April 2000, the authors of Black Mass describe the origin and development of the book. What started as a Boston Globe series about brothers James and William “Billy” Bulger—the former a notorious career criminal, the latter a rising politician in the Massachusetts Senate—took a detour caused by a major question that kept resurfacing: Was James “Whitey” Bulger actually an informant for the FBI? And was that the reason behind Whitey’s seemingly charmed survival and success?
At first, none of the journalists involved in the series could believe it. Whitey had a reputation as a stand-up guy in his South Boston neighborhood. But that didn’t mean he was a good guy, only that he was a loyal one. More than that, he was known for expecting complete loyalty in return. In the Irish underworld of Boston, to be a snitch was an unforgiveable crime. Surely the biggest Irish mob boss of all wouldn’t commit such a heinous offense. And yet, the journalists found it hard to ignore the hints and whispers from local law enforcement, who insisted that no mobster, not even Whitey Bulger, could be so careful as to avoid arrest for more than twenty years. No case that they tried to build against him ever stuck. So the idea that he was protected by someone higher up just wouldn’t go away.
Globe reporters took the whispers as incentive to keep digging. And what they eventually turned up was consistent evidence of a “devil’s deal” between Whitey Bulger and FBI agent John Connolly beginning in 1975 and continuing until 1998: more than twenty years of criminal corruption at the heart of the FBI. For while Bulger may have started out as an informant, the mobster slowly managed to turn the tables until he was the one calling the shots, and the federal agent was the one breaking the law.
Introduction to the Paperback Edition
In this brief note, added to a new edition of Black Mass and dated January 2012, Dick Lehr and Gerard O’Neill update readers on new developments in the case—notably, the murder conviction of John Connolly and the capture and arrest of James “Whitey” Bulger.
In 2008, Connolly was convicted of second-degree murder for his involvement in the killing of a potential witness. He is serving his sentence in a Florida prison.
In 2011, after more than fifteen years as a fugitive, Whitey Bulger was discovered living with his girlfriend in California. He was captured and arrested, bringing some closure to the story told in Black Mass.
Chapter One: 1975
In 1975, thirty-five-year-old FBI agent John Connolly had just been transferred back to his hometown of Boston, and he was determined to make a name for himself. The way to do that, he decided, was to lure in the informant that nobody else has managed to land: James “Whitey” Bulger, a racketeer who had already earned an impressive reputation within the Irish mob—and the FBI’s files. While the FBI had tried to recruit Bulger before with no success, Connolly had a “hook” that previous agents lacked: He and Whitey had grown up in the same neighborhood, South Boston, commonly known as “Southie.” They were kin, of a sort, both children of Irish immigrants. Connolly thought Bulger would trust him. He was right.
Connolly used their shared history, and Bulger’s desire to get rid of his rivals in La Cosa Nostra (LCN), the Italian Mafia, to convince Whitey to become an informant for the FBI. Bulger had been uncertain when the FBI first came sniffing around, discussing it with a trusted confidant, a mobster called Stevie “The Rifleman” Flemmi. What Bulger didn’t know was that Flemmi had been an informant for more than a decade and saw Bulger’s “ratting” as a way to improve his own status.
Connolly didn’t ask Bulger to inform on his own people, but rather on the Mafia, who were already making things difficult for Bulger’s Winter Hill gang. He promised that if Bulger helped them go after LCN, he would be safe from the FBI. Within two weeks of their first meeting, Bulger agreed to the deal. Connolly had landed the elusive Whitey Bulger.
Chapter Two: South Boston
Understanding Connolly and Bulger as adults requires understanding their background as children...