Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (4 page)

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.

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.”

This 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.