WHITEY BULGER WOULD BE in prison today if not for his politically powerful brother, William Bulger. William Bulger would almost certainly have gone to prison if not for his gangster brother Whitey’s connections with the FBI. The man who kept them both out of prison is former FBI honcho and Southie homeboy, John Connolly; yet it is John Connolly who will soon be going to prison if convicted of racketeering charges he is now facing. In the final irony, Connolly’s “get out of jail free card” bears the mug shots of the Bulger brothers. Connolly’s best chance of escaping the prison sentence he deserves is by telling the truth — the real truth that nobody seems to want to hear about the deep connection between the “bad” Bulger and the “good” Bulger. Connolly is one of the few people who knows the truth, but he isn’t saying, at least not so far.
The conventional wisdom is that the FBI made a deal with Whitey Bulger in exchange for information about the Italian mob. I don’t believe that’s all there was to it, since the deal was so one-sided. Whitey Bulger gave the FBI little of value, and the FBI gave him a blank check to commit extortion, drug conspiracy, money laundering, and more. They may even have blocked a murder indictment. They also obstructed justice by tipping off Whitey to wiretaps, strings, and indictments.
The story goes much deeper than a traditional informer deal gone sour. I believe Whitey Bulger bought John Connolly and Connolly’s boss, John Morris. In the end, the “informer deal” became a cover for out-and-out corruption. By the time William Bulger was under investigation for extortion involving his receipt of $240,000 in the 75 State Street scandal, Whitey Bulger owned Connolly and Morris.
Part of the payment made by Whitey Bulger to buy these corruptible FBI agents involved then-Senate President William Bulger. The “good” Bulger was Boston’s most powerful political fixer and patronage dispenser. Billy Bulger’s influence was for sale, and Connolly wanted to be on the receiving end. The two grew up together, and Connolly had worked on Bulger’s first political campaign. Describing the Senate President as “a lifelong friend… a mentor…,” the rogue FBI agent “worked the relationship hard inside the FBI, parading agents through Bulger’s Senate office to meet the President in person,” according to Black Mass: The Irish Mob, the FBI, & a Devil’s Deal, by veteran Boston Globe reporters Dick Lehr and Gerard O’Neill. Connolly also dangled the prospect of quids for quos: “Connolly often told colleagues that Bulger could help them get high-paying jobs when they retired.” Connolly himself ended up with a six-figure lobbying job with “a company that had long curried favor with Senate President William Bulger.”
William Bulger was used not only to dangle the carrot of corruption in front of law-enforcement officials, but also to wield the stick. After a highly decorated state trooper seized Whitey at Logan Airport with a bagful of cash, the political establishment saw to it that the trooper’s career was destroyed. The trooper, who later committed suicide, saw it as payback by Billy. When state officials began to investigate Whitey for drug and organized-crime offenses, Billy saw to it that the state Senate passed what Lehr and O’Neill called “an anonymous amendment to the state budge that struck back” at Whitey’s tormentors by forcing them to retire or take a pay cut. The amendment was eventually vetoed, but the message had been sent: law-enforcement officials go after Whitey at the risk of financial recrimination from Billy; they play ball with Whitey with the prospect of high-paying jobs when they retire.
Connolly claimed that “his friendship with Billy convinced Whitey to become an informant.” I believe he has it backward: It was Connolly’s friendship with William Bulger and Connolly’s hope of capitalizing on it financially that led him to give Whitey a blank check on committing crimes, a heads up on wiretaps, and a head start in evading arrest. Informants simply don’t get that kind of deal, even if they provide invaluable information. Whitey provided little and got everything in return. But it was not only in return for the meager information Whitey provided. It was also in return for what Connolly received and expected from William Bulger.