IN THE EARLY MONTHS of 1982, a low-level hoodlum named Brian Halloran told the FBI that James J. “Whitey” Bulger and Stephen “the Rifleman” Flemmi had ordered the murder, in May 1981, of an Oklahoma businessman named Roger Wheeler. The trigger man was a serial hit man named John Martorano, Halloran went on to say, and the motive was greed: Wheeler suspected Bulger and Flemmi, who controlled the Irish Mob in Boston, were skimming profits from his jai alai fronton in Connecticut.
Brian Halloran told the FBI that story not because testifying against murderers is the right thing to do, but because he was in trouble. He was, in fact, about to stand trial on a murder charge of his own. And in the foggy world of crime and punishment, Halloran knew, the government will often forgive a killer if he can help convict someone prosecutors consider to be a more evil killer. Whether Halloran was telling the truth is irrelevant (though he likely was, considering Martorano has since admitted shooting Wheeler); the more pressing issue is whether the government, in balancing on killer against another, considered Halloran’s information to be worth pursuing.
The FBI decided it was not. Bulger and Flemmi, in the government’s collective mind, were more convenient criminals than Halloran. Twenty years ago, the Justice Department was still obsessing over La Cosa Nostra, “this thing of ours,” which is what Italian crooks call the Mafia. In order to arrest and convict Mafiosi, the FBI routinely employed other criminals, essentially trading immunity for intelligence. In that context, Bulger and Flemmi, who were the local Mafia’s rivals but still occasional partners, were extremely valuable bad guys. Both for years had been what the FBI calls Top Echelon informants, which means they were among the most criminally adept in the stable of snitches.
John Connolly was the FBI agent who handled Bulger and Flemmi. Connolly, a South Boston native with an unfortunately gangsterish coif, was quite good at getting criminals to rat on each other. During his 22 years with the FBI, he convinced a dozen men to become TEs. Knowledge supplied by those informants, in turn, helped produce some of the government’s most celebrated cases against organized crime, including the 1989 taping of a grotesquely sophomoric Mafia induction ceremony. For his contributions, Connolly was considered a hero of sorts, commended by his Washington bosses on nine separate occasions.
The downside, of course, is that Bulger, Flemmi, and the rest of the TEs were allowed to continue being criminals. “There was no moral justification because it was never a moral decision,” Connolly explained once. “This was a business decision. This is a business we’re in, the business of eradicating crime. And to do that, you need criminal informants.”
John Connolly did not concoct that queasy philosophy. He learned it from superiors who learned it from theirs. In hindsight, giving Bulger and friends a free pass in exchange for the local Italian gangsters was a lousy bargain; when the history of the Mafia is penned in a musty Palermo coffeehouse, Boston’s underbosses will merit a footnote at best. For Brian Halloran, it was a fatal arrangement. On May 11, 1982, after the FBI cut him loose, he was shot to death. A friend who happened to be with him also was killed.