Black Mass

Connolly always remained deferential to the older Bulger, calling him by the birth name he preferred, Jim, rather than the street name that the media preferred. Such things might have seemed like petty details, but they were details that made the deal palatable. Bulger, for example, insisted that he would provide information only on the Italian Mafia, not on the Irish. Moreover, he insisted that Connolly not tell his brother Billy, then a state senator, about this new “business deal.”

There was a certain charged and inescapable irony to this deal between Bulger and the FBI, coming as it did during the second year of court-ordered busing in South Boston. The tableau, in its entirety, was bizarre. The people of Southie, including leaders like Billy Bulger, had been helpless in their efforts to repel the federal government, which was plowing through the neighborhood to enforce busing. The federal authority was mighty and despised and would not go away. This was the harsh reality of the neighborhood’s public life. But in a different part of Southie, Whitey Bulger had cut a deal that would freeze the feds. The FBI needed Whitey and would not be looking to do him in. The rest of the world might belong to the feds, but at least the underworld did not. Whitey had found a way to keep them out of his Southie. In an odd way he’d succeeded where his brother had not.

Immediately the information highway was up and running. More meetings were held. Bulger blended in Flemmi, and a package deal was forged. For his part, Bulger clearly recognized the value of teaming up with Flemmi, given Flemmi’s rich access to mafiosi and the kind of information Connolly so badly wanted. Flemmi, meanwhile, had to recognize the value of teaming up with Bulger, not just for his cunning mind but also for his marquee status, particularly with Connolly. He could see something special pass between them right from the beginning. “They had a relationship.”

For Connolly, Flemmi was a hand-me-down, but Bulger was his own, a coup for the FBI in Boston. It was a beast of a deal, a high-five achievement, with Connolly in charge of two midlevel gangsters positioned to assist the FBI in its stated campaign to cripple the Mafia enterprise. But the new deal hardly meant Whitey would curb his style. In fact, just five weeks after the Whitey Bulger informant file was opened officially on September 30, 1975, Whitey chalked up his first murder while on FBI time. He and Flemmi took out a longshoreman from Southie named Tommy King. The hit was part power grab, part revenge, and mostly Bulger hubris. Bulger and King, never friends, had gotten into an argument one night in a Southie bar. Fists began flying. King had Bulger down and was pounding away on him when others finally pulled him off. Payback for Bulger came November 5, 1975. No doubt buoyed by the secret knowledge the FBI would always be looking to curry favor with him, Bulger, Flemmi, and an associate jumped King. The longshoreman vanished from Southie and the world. Not surprisingly, Bulger mentioned none of this in his meetings with Connolly; instead, one of Bulger’s first reports was that the Irish gang unrest and bloodshed supposedly pending between Winter Hill and the Mafia had fizzled—much ado about nothing. The streets were calm, reported Bulger.

So it began.

CHAPTER TWO

South Boston

In order to wait for Whitey at Wollaston Beach, John Connolly had to first get himself home from New York. Flemmi’s boyhood pal “Cadillac Frank” Salemme would be his ticket.

Salemme’s arrest happened on a cold bright New York afternoon in December 1972 when the good guys and the bad guys floated past each other on Third Avenue. A face in the crowd suddenly clicked with Connolly, who told his FBI companions to unbutton their winter coats and draw their guns. A slow, almost comical footrace on snow ended with jewelry salesman Jules Sellick of Philadelphia protesting that he was not Frank Salemme of Boston, wanted for the attempted murder of a mobster’s lawyer. But indeed he was.

The young agent had no handcuffs with him and had to stuff Salemme into a taxi at gunpoint and bark at the bewildered cabbie to drive to the nearby FBI headquarters at East Sixty-ninth and Third. His boss chided him good-naturedly about the handcuffs, but there were envious smiles and back slaps all around for bagging one of Boston’s most wanted mobsters. Some were amazed that Connolly had been able to recognize Salemme, but in fact it wasn’t quite as lucky as it first appeared. An old pro in the Boston FBI office had taken a shine to Connolly and earlier had sent him photographs and likely locations for spotting Salemme, gleaned from informant reports. It was a perfect example of how valuable informants could be. Connolly’s apprehension of Cadillac Frank resulted in a transfer back home, an unusually quick return for an agent with only four years of duty under his belt.

By 1974 Salemme was off to fifteen years in prison and Connolly was back to the streets of his boyhood. By this time Bulger was the preeminent Irish gangster in the flagrantly Irish neighborhood of South Boston. When Connolly returned, Bulger had just solidified his hold on Southie’s gambling and loan-sharking network, the culmination of a slow steady climb that began in 1965 with his release from the country’s toughest prisons.

The two men spoke the same language and shared deep roots in the same tribal place. They came together as book ends on the narrow spectrum of careers available to Irish Catholics who lived in splendid isolation on the spit of land jutting into the Atlantic Ocean. Their cohesive neighborhood was separated from downtown Boston by the Fort Point Channel and a singular state of mind. For decades Southie had been immigrant Irish against the world, fighting first a losing battle against shameful discrimination by the Yankee merchants who had run Boston for centuries, and then another one against mindless bureaucrats and an obdurate federal judge who imposed school busing on the “town” that hated outsiders to begin with. Both clashes were the kind of righteous fight that left residents the way they liked to be: bloodied but unbowed. The shared battles reaffirmed a view of life—never trust outsiders and never forget where you come from.

A retired cop once recalled the constricted choices a young man had coming of age in the South Boston of the 1940s and 1950s. Armed services. City hall. Utility companies. Factory work. Crime. “It was gas, electric, Gillette, city, cop, crook,” he said. The decades of travail made Southie residents quick to fight for limited opportunities.

Bulger and Connolly, crook and cop, grew up in the first public project in Boston, a spartan village of thirty-four tightly spaced brick tenement buildings. It was built by a contractor friend of the legendary Mayor James Michael Curley with money from the Public Works Administration of Franklin Delano Roosevelt. Both men were revered in the Bulger home on Logan Way—Curley for his roguish repartee and Roosevelt for saving the workingman from the ravages of capitalism.