1975 - The Prince of Darkness is a gentleman - Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)


The Prince of Darkness is a gentleman.




Under a harvest moon FBI agent John Connolly eased his beat-up Plymouth into a parking space along Wollaston Beach. Behind him the water stirred, and further off, the Boston skyline sparkled. The ship-building city of Quincy, bordering Boston to the south, was a perfect location for the kind of meeting the agent had in mind. The roadway along the beach, Quincy Shore Drive, ran right into the Southeast Expressway. Heading north, any of the expressway’s next few exits led smack into South Boston, the neighborhood where Connolly and his “contact” had both grown up. Using these roads, the drive to and from Southie took just a few minutes. But convenience alone was not the main reason the location made a lot of sense. Most of all, neither Connolly nor the man he was scheduled to meet wanted to be spotted together in the old neighborhood.

Backing the Plymouth into the space along the beach, Connolly settled in and began his wait. In the years to come Connolly and the man he was expecting would never stray too far from one another. They shared Southie, always living and working within a radius of a mile of each other in an underworld populated by investigators and gangsters.

But that came later. For now Connolly waited eagerly along Wollaston Beach, the thrum of the engine a drag to the buzz inside the car that was like an electric charge. Having won a transfer back to his hometown a year earlier, he was poised to make his mark in the Boston office of the nation’s elite law enforcement agency. He was only thirty-five years old, and this was going to be his chance. His big moment in the FBI had arrived.

The nervy agent was coming of age in an FBI struggling with a rare public relations setback. In Congress, inquiries into FBI abuses had confirmed that the late FBI director J. Edgar Hoover had for years been stockpiling information on the private lives of politicians and public figures in secret files. The FBI’s main target, the Mafia, was also in the news. Swirling around were sensational disclosures involving a bizarre partnership between the CIA and the Mafia also unearthed during congressional investigations. There was talk of a CIA deal with mafiosi to assassinate Cuba’s Fidel Castro as well as murder plots that involved poisoned pens and cigars.

Indeed, it suddenly seemed like the Mafia was everywhere and everyone wanted a piece of the mysterious and somehow glamorous organization, including Hollywood. Francis Ford Coppola’s movie masterpiece, The Godfather, Part II, had played to huge audiences when it opened the year before. A few months earlier the picture had won a slew of Oscars. Connolly’s FBI was now deeply into its own highly publicized assault on La Cosa Nostra (LCN). It was the FBI’s number-one national priority, a war to counter the bad press, and Connolly had a plan, a work-in-progress to advance the cause.

Connolly surveyed the beachfront, which at this late hour was empty. Occasionally a car drove past him along Quincy Shore Drive. The bureau wanted the Mafia, and to build cases against the Mafia, agents needed intelligence. To get intelligence, agents needed insiders. In the FBI the measure of a man was his ability to cultivate informants. Connolly, now seven years on the job, knew this much was true, and he was determined to become one of the bureau’s top agents—an agent with the right touch. His plan? Cut the deal that others in the Boston office had attempted, but without success. John Connolly was going to land Whitey Bulger, the elusive, cunning, and extremely smart gangster who was already a legend in Southie. The stylish FBI arriviste wasn’t the type to take the stairs. He was an elevator man, and Whitey Bulger was the top floor.

The bureau had had its eye on Bulger for some time. Previously, a veteran agent named Dennis Condon had taken a run at him. The two would meet and talk, but Whitey was wary. In May 1971 Condon managed to elicit extensive inside information from Whitey on an Irish gang war that was dominating the city’s underworld—who was allied with whom, who was targeting whom. It was a thorough, detailed account of the landscape with an accompanying lineup of key characters. Condon even opened an informant file for Whitey. But just as quickly, Whitey went cold. They met several times throughout the summer, but the talks didn’t go well. In August, reported Condon, Whitey was “still reluctant to furnish info.” By September Condon had thrown up his hands. “Contacts with captioned individual have been unproductive,” he wrote in his FBI files on September 10, 1971. “Accordingly, this matter is being closed.” Exactly why Whitey ran hot then cold was a mystery. Maybe the all-Irish nature of the intelligence he’d provided had proved discomforting. Maybe there was a question of trust: why should Whitey Bulger trust Dennis Condon of the FBI? In any event, the Whitey file was closed.

Now, in 1975, Condon was on the way out, his eye on his upcoming retirement. But he’d brought Connolly along, and the younger agent was hungry to reopen the Whitey file. After all, Connolly brought something to the table no one else could: he knew Whitey Bulger. He’d grown up in a brick tenement near the Bulgers’ in the Old Harbor housing project in South Boston. Whitey was eleven years older than Connolly, but Connolly was oozing with confidence. The old neighborhood ties gave him the juice others in the Boston office didn’t have.

Then, in an instant, the waiting was over. Without any warning, the passenger side door swung open, and into the Plymouth slipped Whitey Bulger. Connolly jumped, surprised by the suddenness of the entry, surprised he was caught unaware. He, a trained federal agent, had left his car doors unlocked.

“What the hell did you do, parachute in?” he asked as the gangster settled into the front seat. Connolly had been expecting his visitor to pull up in a car alongside him. Bulger explained that he had parked on one of the side streets and then walked along the beach. He’d waited until he was sure no one else was around, and then he’d come up behind from the water.

Connolly, one of the younger agents on the prestigious Organized Crime Squad, tried to calm himself. Whitey, who’d just turned forty-six on September 3, sat in the front seat, larger than life, even if he just barely hit five-feet-eight and weighed an ordinary 165 pounds. He was hard bodied and fit, with penetrating blue eyes and that signature blond hair, swept back. Under the cover of darkness the two men began to talk, and then Connolly, properly obsequious to a neighborhood elder who was also an icon, made his offer: “You should think about using your friends in law enforcement.”

▪ ▪ ▪

This was Connolly’s pitch to Whitey: you need a friend. But why?

In the fall of 1975 life in the city was tumultuous and changing unpredictably. From where they sat along the vacant beach, the two men could see the Boston skyline across the water. At the time the unexpected good fortunes of their Red Sox electrified the citizens of Boston. Yaz, Luis Tiant, Bill Lee, Carlton Fisk, Jim Rice, and Fred Lynn—who, after the season, would be honored as both the rookie of the year and the American League’s most valuable player—were in the midst of a glorious run for the World Series title against the powerful Cincinnati Reds.

But closer to home the world was dark and unstable.

The nightmare of busing had begun its second year. In 1974 a federal court order to bus black students from Roxbury to South Boston High School in order to achieve racial balance in the city’s segregated public schools had turned the neighborhood into a war zone. The rest of the country tuned in, and people were getting to know Southie through televised images and front-page newspaper photographs featuring riot police, state troopers patrolling school corridors, rooftop police snipers, and legions of blacks and whites screaming racist chants at one another. The Pulitzer Prize in photography was awarded for a jaw-dropping 1976 picture of a black man being rammed with an American flag during a disturbance outside of city hall. Nationwide the neighborhood was seen through a prism of broken glass—a bloodied first impression that was searing and horrific.

Whitey’s younger brother Billy was in the middle of it all. Like all the neighborhood’s political leaders, Billy Bulger, a state senator, was an implacable foe of the court-ordered busing. He never challenged the court’s findings that the city’s schools were egregiously segregated. He did, however, strongly oppose any remedy that forced students to travel out of their home school districts. He’d gone to Washington, DC, to complain and present their case to the state’s congressional delegation, and once there, he delivered a speech to a group of antibusing parents in the pouring rain. He hated the view outsiders were getting of his neighborhood, and he denounced the “unremitting, calculated, unconscionable portrayal of each of us, in local and national press, radio and television, as unreconstructed racists.” To him the issue was his neighbors’ legitimate worry for the welfare and education of their children. Back home Billy Bulger spoke out regularly against the unwanted federal intervention.

But busing would not go away, and the summer that had just ended had not gone well. In July six young black men had driven to Carson Beach in South Boston and ended up in a fight with a gang of white youth that left one black hospitalized. In his younger days John Connolly had been a lifeguard along the beaches of South Boston, just as Billy Bulger had been before him, and now the sandy beaches had become another battleground. On a Sunday in August police helicopters circled over Carson Beach and Coast Guard boats patrolled offshore while more than one thousand black citizens drove to the beach in a motorcade of several hundred cars. They were accompanied on their “wade-in” to the beach by more than eight hundred uniformed police officers. The cameras rolled.

By the time Connolly had arranged to meet Whitey along Wollaston Beach, the schools had reopened. Student boycotts and fights between blacks and whites were regular events. Thinking it might help ease the racial tension, officials for the first time tried to integrate the football team at South Boston High School. But the four black players who reported to the first practice had to do so under police protection.

The neighborhood was torn apart, and Connolly knew that, could feel that pain, because it was his neighborhood as well, and he had played off this bond in lining up his meeting with Bulger. But although the bond might have gotten him an audience with Whitey, he now had to pitch a deal to his boyhood hero. Connolly most of all wanted to exploit the wider underworld troubles brewing between the Boston Mafia and a gang Bulger had signed on with in neighboring Somerville. Bulger, in charge now of the rackets in Southie, had hooked on with the Somerville crime boss Howie Winter. The gang operated out of a garage in the Winter Hill section of the small city just across the Charles River to the west. In the past year Whitey had paired off with another member of the gang, Stevie “The Rifleman” Flemmi. They got along, found they had certain things in common, and had begun to hang out.

By the time Connolly and Bulger met, the young FBI agent had done his homework. He knew Bulger and the Winter Hill gang were facing a two-pronged threat from a local Mafia that for decades was controlled by the powerful underboss Gennaro J. Angiulo and his four brothers. Pending at that moment was a dispute between the two organizations over the placement of vending machines throughout the region. There had been wiseguy bluster about shootouts as a way to settle the matter. With all this instability, Connolly argued, a wiseguy could use a friend.

Besides, Angiulo was wily and inscrutable. He had a knack for setting up for arrest those he no longer had any use for. For example, a few years earlier a mob enforcer had veered out of his control. Angiulo, the story went, had reached out to his contacts inside the Boston Police Department, and the mob renegade was soon picked up on phony gun charges after crooked cops planted weapons in his car. No one knew for certain whether Angiulo in fact had the kind of access to manipulate an arrest like that. But this was the story making the rounds, and Whitey Bulger and the rest of Howie Winter’s gang believed it. As Connolly well knew, perception was all that actually mattered.

Bulger was clearly concerned about Angiulo setting him up. “What if three cops stop me at night and say there was a machine gun in my car?,” Whitey had complained. “Who is the judge gonna believe? Me or the three cops?” Connolly had positioned himself to play off such crosscurrents of underworld paranoia.

The two men sat in the Plymouth, the city lights rippling on the water. “You should use your friends,” Connolly stressed—a line that caused Bulger to consider the agent intently, sensing an opening for the upper hand.

“Who?,” Whitey asked at last. “You?”

“Yeah,” replied Connolly to a ruthless man who used up people and threw them away. “Me.”

▪ ▪ ▪

Connolly’s proposal was simple: inform on La Cosa Nostra and let the FBI do the rest. Bulger knew, Connolly recalled, “that if we were chewing on the Mafia, it was very difficult for the Mafia to be chewing on them.”

In fact, the moment Connolly had indicated he wanted a meeting Bulger knew what the FBI wanted. For weeks Bulger had already been working the proposition over in his mind, weighing the pros and cons, figuring the angles and potential benefits. He’d even gone and consulted with Stevie Flemmi. Bulger brought up the subject one day when the two of them were in Somerville at Marshall Motors, the auto repair shop Howie Winter owned. The one-story garage was a faceless building made of cinder blocks. It resembled a concrete bunker and served as a business front for the gang’s wide-ranging illegal enterprises, which since 1973 had expanded to include fixing horse races up and down the East Coast.

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 member of the Mafia, 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 weighed 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 although 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 and 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, 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 that 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, Rico 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, 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 grunt work 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 whom 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, through the years 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 always 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 Connolly was surely thinking about his career, the deal wasn’t about what might come; instead, 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 that Whitey would curb his style. In fact, just five weeks after the Whitey Bulger informant file was officially opened 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.