Black Mass

by Dick Lehr

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.

  Even though Rico had instructed Flemmi that he was not to consider himself an employee of the FBI and had gone over with Flemmi some of the FBI’s other ground rules for informants, the agent and Flemmi regarded most of those instructions as an annoying formality. What was important was that Rico had promised Flemmi he would keep confidential the fact that Flemmi was his informant, and this was the key to their alliance. It was a pledge most agents customarily gave to their informants, a pledge viewed as “sacred.” But in Rico’s hands the promise was sacred above all else, even if it required that he commit the crime of aiding and abetting a fugitive. Rico promised that as long as Flemmi worked as his informant he would see to it that Flemmi wasn’t prosecuted for his criminal activities.

  For obvious reasons, such a deal had proven advantageous for Flemmi. He also liked how Rico did not treat him like some kind of lowlife gangster. Rico wasn’t the pompous G-man ready to spray the room with disinfectant immediately after he’d left. He was more like a friend and an equal. “It was a partnership, I believe,” said Flemmi.

  Eventually the criminal charges against Flemmi were dropped, after key witnesses recanted, and in May 1974 Flemmi was able to end his fugitive life and return to Boston. With the help of the FBI, he’d survived the gang wars and outlasted the murder and car bombing charges. But Flemmi had no intention of going straight. Once back in Boston he’d hooked up with Howie Winter and gone back to what he knew best. And now he was standing alongside Whitey Bulger at Marshall Motors. “Should I meet him?” Bulger had asked. Flemmi thought for a moment. He had been back less than a year, and it was obvious to him that things were in flux. It was clear that some new arrangement was in the works. He’d even met on his own with Dennis Condon, a short meeting at a coffee shop where he was introduced to John Connolly. Flemmi regarded all the huddling as a kind of “transition,” with Connolly being set up to take over now that Paul Rico was transferred to Miami and nearing retirement. Over time, of course, Flemmi had experienced a strong upside to his FBI deal. But he was just Stevie Flemmi, not the already legendary Whitey Bulger.

  Flemmi cautiously opted for a short answer. It was an answer soaking in subtext, but short nonetheless.

  “It’s probably a good idea,” he told Bulger. “Go and talk to him.”

  CONNOLLY wasn’t in any rush to make his pitch. “I just want you to hear me out,” he told Bulger in the car along Wollaston Beach. Connolly carefully played up the double-barreled threat that Bulger and his Winter Hill gang presently faced from Gennaro Angiulo’s Mafia. “I hear Jerry is feeding information to law enforcement to get you pinched,” he told Bulger. They talked about how Jerry Angiulo definitely had an advantage over the rest of the field, able to call on a crooked cop to do him a favor. “The Mafia has all the contacts,” Connolly said.

  Then Connolly moved along and stoked the vending machine dispute. Word on the street, observed Connolly, was that Zannino was ready to take arms against Bulger and his friends in the Winter Hill gang. “I’m aware that you’re aware that the outfit is going to make a move on you.”

  This last remark especially caught Bulger’s attention. In fact, the LCN and Winter Hill had always found a way to coexist. Not that there weren’t disputes to work out, but the two groups were closer to being wary partners than enemies on the verge of a war. Even the vitriolic and unpredictable Zannino, the Mafia’s Jekyll and Hyde, could one moment angrily denounce Winter Hill and promise to mow them down in a hail of bullets and then suddenly turn operatic and proclaim lovingly, “The Hill is us!” Truth be told, Gennaro Angiulo was at this time more concerned about threats he was receiving from a runaway Italian hothead known as “Bobby the Greaser” than he was about imminent war with Winter Hill. But for Connolly’s purposes, it was better to play up the beef percolating between the LCN and Winter Hill over the vending machines, and Connolly could tell right away he’d hit a hot button with the fearless Bulger when he mentioned the potential for violence. Bulger was clearly angered.

  “You don’t think we’d win?” Bulger shot back.

  Connolly actually did think Bulger could prevail. He fully believed Whitey and Flemmi were much tougher than Angiulo and his boys—“stone killers” he called Bulger and Flemmi. But that wasn’t the point.

  “I have a proposal: why don’t you use us to do what they’re doing to you? Fight fire with fire.”

  The deal was that simple: Bulger should use the FBI to eliminate his Mafia rivals. And if that alone wasn’t reason enough, the FBI wouldn’t be looking to take Bulger himself down if he were cooperating. In fact, at that moment other FBI agents were sniffing around and making inquiries into Bulger’s loan-sharking operations. Come aboard, Connolly said. We’ll protect you, he promised. Just as Rico had promised Flemmi before him.

  Bulger was clearly intrigued. “You can’t survive without friends in law enforcement,” he admitted at night’s end. But he left without committing.

  Two weeks later Connolly and Bulger met again in Quincy, this time to cement the deal.

  “All right,” he informed Connolly, “deal me in. If they want to play checkers, we’ll play chess. Fuck them.”

  Th
is was music to John Connolly’s ears. Incredibly, he’d just brought Whitey Bulger into the FBI. If developing informants was considered the pinnacle of investigative work, Connolly was now, he proudly concluded, in the big leagues. In a single bold stroke he’d put FBI gruntwork behind him and now belonged to an upper crust occupied by the likes of the retiring Paul Rico. If, in Connolly’s mind, Rico was the agent a slew of the new young turks in the office wanted to model themselves after, Bulger was the neighborhood legend all the kids in Southie were in awe of. Connolly had to sense that the moment marked the slick merger of both worlds.

  Moreover, this particular deal had a certain élan to it. The last gangster anyone in Boston would suspect of being an FBI informant was Whitey Bulger of South Boston. Indeed, Connolly was always sensitive to this seeming incongruity. Among his FBI colleagues Connolly rarely, if ever, called Bulger an informant, a rat, a snitch, or a stoolie. He would still grate when he later heard other people use those labels. To him Bulger was always a “source.” Or he used the terms that Bulger requested: “strategist” or “liaison.” It was as if even the man who convinced Whitey to become an informant couldn’t believe it himself. Or maybe it was just that the deal from the beginning was less a formal understanding with the FBI than a renewed friendship between Johnny and Whitey from Old Harbor. And though John Connolly was surely thinking about his career, the deal wasn’t about what might come—it was about where he had come from. A circle, a loop, the shape of a noose. All roads led to Southie.

  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.

  Connolly’s parents—John J. Connolly, a Gillette employee for fifty years, and his stay-in-the-background mother, Bridget T. Kelly—lived in the project until John was twelve years old. In 1952 the family moved “up” to City Point, which was Southie’s best address because it looked out to sea from the far end of the promontory. Connolly’s father was known as “Galway John,” after the Irish county of his birth. He made the church, South Boston, and his family the center of his life. Somehow the father of three children pulled the money together to send John to the Catholic school in the Italian North End, Columbus High. It was like traveling to a foreign country, and John Jr. joked about a commute that required “cars, buses, trains.” The Southie instinct for patriotic duty and a public payroll also led Connolly’s younger brother James into law enforcement. He became a respected agent with the U.S. Drug Enforcement Administration, a subdued version of his swaggering older brother.

  The Connollys and Bulgers reached adolescence in a clean, well-lit place by the sea surrounded by acres of parks and football and baseball fields and basketball courts. Sports were king. Old Harbor had intact families, free ice cream on the Fourth of July, and stairwells that were club-houses, about thirty kids to a building. The twenty-seven-acre project was the middle ground between City Point, with its ocean breezes and lace curtains, and the more ethnically diverse Lower End, with its small box-shaped houses that sat on the edge of truck routes leading to the factories and garages and taverns along the Fort Point Channel. To this day the neighborhood consistently maintains the highest percentage of long-term residents in the city, reflecting a historic emphasis on staying put rather than getting ahead that engenders fierce pride. As South Boston bowed slightly to gentrification along its untapped waterfront in the late 1990s, its city councilor sought to reaffirm traditional values by outlawing French doors on cafés and roof decks on condos facing the sea.