Black Mass

Bulger told Flemmi that the FBI agent John Connolly was making a bid for his services. “What do you think?” Bulger asked Flemmi when the two were alone. “Should I meet him?”

The question hung in the air. Flemmi later decided that, if Whitey Bulger was confiding in him about an FBI overture, he was signaling that he already knew something about Flemmi’s own secret “status.” Flemmi had a history with the Boston FBI, and what a history it was. He was first enlisted as an FBI informant in the mid-1960s. Flemmi adopted the code name “Jack from South Boston” for his dealings with his FBI handler, an agent named H. Paul Rico (who was Dennis Condon’s partner).

Rico, a dashing senior agent who favored a Chesterfield topcoat and French cuffs, cultivated Flemmi because of his access to the New England Mafia. Flemmi was not a made Mafia member, but he knew all the leading players and was frequently in their company. The Mafia liked Flemmi, a former army paratrooper who went from a juvenile detention center at age seventeen to serve two tours of duty in Korea with the 187th Airborne Regimental Combat Team. He had a reputation as a tough killer, even if he was only average in height, five-feet-eight, and in weight about 140 pounds. Flemmi worked on his own, out of his Marconi Club in Roxbury, a combination bookie joint, massage parlor, and brothel, where he got messages, took calls, and held meetings. A popular guy with his curly chestnut hair and brown eyes, a guy who enjoyed cars and the late-night company of young women, Flemmi got around.

Even the New England godfather, Raymond L. S. Patriarca, revealed a fondness for him. In the winter of 1967 Flemmi was summoned to Providence. He dined with Patriarca and Patriarca’s brother Joe, a lunch that lingered long into the afternoon. They talked about family. Patriarca asked Flemmi where his parents were from in Italy. They talked about business. Patriarca promised to steer cars to the new auto body shop Flemmi had opened. They talked a bit about Flemmi’s brother, Jimmy the Bear, who was in prison serving time on an attempted murder rap. In a gesture of goodwill, Patriarca gave Flemmi $5,000 in cash to put into the auto shop.

Back in Boston, Flemmi mostly moved around with a boyhood pal, Frank Salemme, whose nickname was “Cadillac Frank.” The two had grown up in Roxbury, where Flemmi’s family lived in the Orchard Park housing project. His father, Giovanni, an immigrant from Italy, had worked as a bricklayer. Flemmi and Salemme worked the streets together as enforcers, bookmakers, and loan sharks. They frequented the North End, the tight-knit Italian neighborhood where underboss Gennaro Angiulo had his office, and they often ended up at late-night blowouts in the company of hard-drinking Larry Zannino.

Zannino was the brutal and bloodless mafioso whom Angiulo relied on to bring muscle to the Boston LCN enterprise. In turn Zannino relied on Flemmi and Salemme to put some of his loan-sharking money out on the street. But while everyone liked Stevie, the feeling was not mutual. Flemmi didn’t trust the North End, not Angiulo and especially not Zannino. When drinking with Zannino, Flemmi would pace himself, careful not to let down his guard. But Zannino and the others didn’t notice, and they took Flemmi further in. There was the night, for example, in the summer of 1967 at Giro’s Restaurant on Hanover Street, a night spent with a lineup of local wiseguys. Zannino, Peter Limone, Joe Lombardi. Flemmi was with Salemme. They ate, drank, and then Zannino insisted they retire to a nearby bar, the Bat Cave.

Over more drinks a slobbering Zannino and Limone indicated that they’d all decided to sponsor Flemmi and Salemme “for membership in our organization.”

Peter Limone, swaggering, then put his arms around Flemmi and Salemme. “Ordinarily, before you’re a member you’d have to make a hit,” confided the senior mobster, “and I’d have to be with you as your sponsor to verify that you made a hit and report how you handled yourself. But with the reputation you two have, this may not be necessary.”

Flemmi wanted no part of joining the Mafia, however, and resisted the recruitment drive. For one thing, he didn’t like the brutal Zannino, who was capable of hugging you one moment and blowing your brains out the next. The same could be said for Angiulo. Besides, Flemmi had Rico, and Rico had Flemmi.

Given the gang war and all the shifting alliances, Flemmi’s life was always up for grabs. More than once he’d told Rico he “was a prime target for an execution,” and in other reports Rico noted that Flemmi had no permanent address because if “the residence becomes known, an attempt will probably be made on his life.” Flemmi grew to rely on Rico to alert him to any trouble the FBI might have picked up from other informants.

More than that, Flemmi came to expect that Rico would not push him about his own criminal activities—not his gaming or his loan-sharking, or even the killings. In the spring of 1967, following the disappearance of gangster Walter Bennett, Flemmi told Rico, “The FBI should not waste any time looking for Walter Bennett in Florida, nor anyplace else, because Bennett is not going to be found.” Rico then asked what actually happened to Bennett. Flemmi shrugged off the inquiry, telling Rico there wasn’t any “point in going into what happened to Walter, and that Walter’s going was all for the best.” Rico simply let the matter go at that. By the late 1960s Flemmi was a suspect in several gangland slayings, but the FBI never pressed him hard to talk about the murders.

In early September 1969 Flemmi was finally indicted by secret grand juries in two counties. He was charged in Suffolk County for the murder of Walter Bennett’s brother William, shot to death in late 1967 and dumped from a moving car in the Mattapan section of Boston. Then in Middlesex County, Flemmi, along with Salemme, was charged in a car bombing that had blown off a lawyer’s leg.

Just before the indictments were handed down, Flemmi received a phone call.

It was early in the morning, and Paul Rico was on the line. “It was a very short, brief conversation,” Flemmi recalled. “He told me that the indictments were coming down, and he suggested that me and my friend leave Boston—leave immediately—or words to that effect.”

Flemmi did just that. He fled Boston and spent the next four and a half years on the lam, first in New York City and then mostly in Montreal, where he worked as a printer at a newspaper. During that time Flemmi often called Rico, and Rico kept him posted about the status of the cases. Rico did not pass along any information about Flemmi’s whereabouts to the Massachusetts investigators who were trying to track him down.