The G-man and the Snitch

Decorated FBI agent John Connolly soon goes on trial for murder in Miami. Too bad he wasn't here when the shots were fired.

John Connolly didn't look dangerous sitting there in Room 7-3 of the Miami-Dade County Courthouse alongside the carjackers, rapists, and robbers.

No, Connolly looked exactly like what he was: a short, stocky 66-year-old guy in handcuffs. His wide face was puffy and red, as if his blood pressure were a touch high. His hue almost matched his attire — a tomato-color jumpsuit.

His mouth and brow were frozen in a perpetual, skeptical scowl. Saggy jowls hung from his jaw. His hair was the only attractive thing about him — thick, gray, and perfectly coiffed.

Whitey Bulger (left, in the Boston cap) and his associate Kevin Weeks
Whitey Bulger (left, in the Boston cap) and his associate Kevin Weeks
Connolly was convicted of racketeering in 2002
Connolly was convicted of racketeering in 2002

While waiting for his hearing, Connolly sat motionless, barely blinking. He didn't fidget with his black wire-rim glasses or look at anyone in the audience. The other prisoners were bodies in motion: throwing gang signs to their friends, blowing kisses to their girlfriends, sighing audibly. They were toothless, tattooed, and goateed, all wearing bright orange jumpsuits.

Connolly soaked it in with Zen-like calm. He eyed the judge as she called each case, followed every lawyer's word with a slight turn of his head. Occasionally he glanced at the other inmates, and his scowl deepened. He kept his hands folded neatly in his lap.

He stood when the judge called his name.

His was one of 60 cases on Judge Barbara Areces's docket that day. The room was packed with defense lawyers, prosecutors, criminals, probation officers, mothers, and a couple of reporters. Almost no one in the room paid attention to the proceedings. The din was so loud that Judge Areces — a smiling brunet with brick-red lipstick — finally pursed her lips: "Shhhh."

Soon Manny Casabielle, a tall, thin lawyer for Connolly, piped up. "My client is a former FBI agent," he said.

The room fell silent. One inmate, mouth open, swiveled his head toward Connolly. Other thugs uneasily glanced at him.

That guy? An FBI agent? In jail?

If they only knew the real story.

That Connolly is a legendary lawman and a Harvard graduate — a hero who helped take down the Italian Mafia in Boston. That he's charged with the 1982 murder of a hard-drinking wannabe gangster named John Callahan. That when Callahan's bullet-riddled body was found stuffed in the trunk of a Cadillac at Miami International Airport, a dime was placed on his stomach — heads up — an old-school way of saying, "Don't snitch."


Connolly was born in Boston on August 1, 1940, to a stay-at-home mom and a factory-worker father originally from Galway, Ireland. Like many of Boston's Irish immigrants in those days, Connolly's father preferred to live, work, and worship near others from the old country.

The Connollys lived on O'Callahan Way, a street tucked in the mazelike Old Harbor housing projects, a village of 34 brick buildings in the neighborhood of South Boston, known to locals as Southie. The projects were built in 1938 as part of the New Deal.

When Connolly was just eight years old, he went into a Southie ice-cream parlor with two friends. A slight, white-haired nineteen-year-old from the projects offered to buy the trio ice-cream cones. Connolly protested. His father told him never to accept things from strangers. The man told the kid that he wasn't a stranger. They were both Irish.

"What kind of ice cream do you want?" he asked.

"Vanilla," Connolly replied.

The man was James Bulger, whose nickname around Southie was Whitey because of his naturally white-blond hair. He had achieved notoriety several years earlier by heisting stuff from delivery trucks and keeping other hoods in line with his fists. Yet he had a soft side, often distributing free turkeys to the poor for Thanksgiving, leading some people to consider him a local Robin Hood.

Some 60 years later, that scene in the ice-cream parlor would be dramatized in The Departed, an Oscar-nominated movie by director Martin Scorcese (due out on DVD this week). Starring in the Connolly role: Matt Damon. A deliciously evil Jack Nicholson plays the Whitey-inspired figure.

In real life, the young Connolly also befriended Whitey's brother Billy, whom he would sometimes follow home from the local Catholic church. Billy was a small, bookish kid who inspired Connolly to read. Still, like most of the boys in Southie, Connolly loved sports and played baseball. People remember how handsome the future FBI agent was in his uniform.

As they grew older, the disparate trio went their separate ways. Billy — short and bearing a strong resemblance to a leprechaun — became a local politician. Whitey — small, slight, and steely-eyed — went to Alcatraz and then Leavenworth prison after a bank robbery conviction in the 1950s. He would later tell people that while in the can, he volunteered to take LSD for a CIA experiment.

Connolly, meanwhile, attended Boston College and then Suffolk Law School at night. By day, he was a high school teacher. In the late 1960s, a friend of a friend introduced him to someone in the local FBI office, and the idea of being a G-man excited him. He took the federal test and passed. That was 1968. He was first assigned to San Francisco and then New York, but he went home briefly in 1970 to marry a local Irish-American girl from Southie, Marianne.

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