"This ain't reality TV"

James "Whitey" Bulger played the criminal game for generations, played it better than most, played it as well as anyone in the last 50 years, played it for so long that he surely knew how it would all turn out. Will he speak at his sentencing in a way that gives comfort to all those whose lives he cruelly touched? Don't bet on it. He's far more likely to go down true to his career, to his horrific choices and to his conscience. That's surely no consolation to the family and friends of his victims who showed up in court every day. But of course that was the whole point of this remarkable life of crime.

He developed and handled two secret informants: Irish mobster James "Whitey" Bulger and Bulger’s partner, Stephen "the Rifleman" Flemmi. In May 2002, a federal jury convicted Connolly of racketeering and obstruction of justice—of being part of Bulger’s mob—and of tipping Bulger and Flemmi to their secret indictment in 1994. (Flemmi claims he and Bulger gave Connolly $235,000 for his services, all told.)

Bulger fled Boston before the cops came with arrest warrants. Flemmi didn’t get out in time. When it became clear that no one in the FBI or Justice Department could protect him, Flemmi finally agreed to talk in 2003. But Connolly never has. And because he didn’t cut a deal—like so many mobsters who testified against him in exchange for lighter sentences—because he "refused to lie," he says, as the Justice Department wanted him to, Connolly is serving a maximum sentence of 10 years.

"The Department of Justice threw him under the bus," says Bob Fitzpatrick, the commander of the FBI’s organized-crime squad and Connolly’s former boss.
The charges he was convicted of, however, pale in comparison with those he faces today. This month Connolly is scheduled for trial on a claim that in 1982 he plotted and committed murder in the first degree, by telling the Bulger mob that if a potential witness sang they were all going to prison.

At Connolly’s last pretrial hearing in July, the black hair had gone gray, the face was puffy, and the once-flashy wardrobe was reduced to a rumpled red jumpsuit. Under the judge’s questions, he showed none of his trademark arrogance or the anger he lets slip during collect calls. Connolly instead nearly entreated the judge to see things his way. "I’m innocent. I’m pleading not guilty."

Connolly says he’s being framed by the same justice system that once commended his work, which is also the same justice system that failed to prosecute the misdeeds of his fellow agents. This trial, like the last, will hinge upon one corrupt supervisor, but also career criminals who have dealt themselves out of the death penalty or long prison sentences by agreeing to testify. If convicted, Connolly is likely to spend the rest of his life in prison. And yet the mobsters who’ve become partners in his prosecution collectively account for about five dozen murders and are, with one exception, out on the street or headed there soon. It appears John Connolly must atone for the sins of everyone: the mobsters, the Justice Department, and the FBI.