Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal by Dick Lehr and Gerard O’Neill


From Marcus Brutus to Judas Iscariot, there are few figures people hate more than the double-crossing informant. In places like 1970s South Boston, there was a rule about it. Never talk to cops. Don’t be a rat. Better to die or rot in jail than snitch. It was a Mafia rule enforced from the top down. If a guy was even suspected of going to the cops, things weren’t going to end well for him. The notorious gangster Whitey Bulger loved to rail against snitches, saying there was nothing he hated more than a rat. But while he publicly denounced them, in private he was feeding information to the FBI.

Whitey Bulger is not someone who could ever be confused for a good guy. The head of the Irish mob in South Boston, he already had a long history of murder, rape, extortion, armed robbery, loan sharking and drug dealing before the FBI ever came knocking on his door. One of his childhood acquaintances was a man named John Connolly, who Whitey once rescued in a playground fight. After joining up with the FBI, the rising star offered Bulger and his associate Stevie Flemmi a deal-inform on the Italian mob and the FBI will turn a blind eye on their own activities.

It soon became apparent that Connolly and his associates liked being gangsters more than they liked being the law. In exchange for what turned out to be a negligible amount of information, the feds gave them carte blanche to commit whatever crimes they wanted, including murder. In some cases, Connolly even helped them. When Connolly and his colleague John Morris learned another gangster was informing against Bulger and Flemmi, they tipped them off, knowing full well what was going to happen to the guy. After they refused to place the informant in witness protection, he was murdered on a South Boston (of course, there were no witnesses. At least none that would talk to the cops). They also warned the gangsters about impending police wiretaps and indictments, enabling them to stay one step ahead of the Boston P.D. All the while, Connolly was writing glowing reports on his informers, trumping up the information they gave and downplaying the crimes the pair were committing. Connolly and Morris invited Bulger and Flemmi to their homes for dinner. Morris even borrowed money from them.  All the while, drugs flowed into the streets of Southie and the body count rose.

Black Mass was an exhaustive, detailed, compelling and incredibly frustrating book. We should all be appalled by the sheer abuse of power committed by individual FBI agents, but it’s getting harder and harder to be surprised by these things anymore. At least this book has a happyish ending. Flemmi and Bulger are (finally) behind bars. The disgraced John Morris was granted immunity to testify against John Connolly, who’s still in jail today. But a cases like this is just the tip of the iceberg of corruption, caused by the FBI’s total failure to monitor the relationship between their agents and informants. Black Mass would have been a fabulous fiction book. Unfortunately, it’s all too real.

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