Bob ’n’ Weave - 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.



Bob ’n’ Weave

The Boston FBI was convinced it needed Bulger and Flemmi, and Paul Rico, Dennis Condon, and John Connolly were going to make the match work, even if that meant dispensing with the Frank Greens of the world, and even if it meant juggling three regulatory hot potatoes—the FBI manual of operations, the attorney general’s guidelines for handling criminal informants, and federal criminal statutes. Luckily for them, Rico had fashioned a “unique” style in his approach to the messy business of managing informants and had set the tone for other handlers in Boston: rules were made to be broken.

It was all worth it, they believed, to get at the Mafia. Throughout the United States the FBI’s field offices were under great pressure to develop informants of a certain kind—top-echelon informants—to wage war against the mob. Much of the pressure was fallout from how embarrassingly late the FBI had been in acknowledging the Mafia. The problem had been J. Edgar Hoover’s intransigence. He preferred piling up statistics on bank robberies and hunting down Communists to taking a hard look at evidence of the Mafia’s existence.

For instance, in November 1957 Mafia leaders convening in the upstate New York town of Apalachin became front-page news after a New York State Police sergeant stumbled upon the invitation-only event. Troopers set up a roadblock, and the Mafia delegates arriving from around the country were sent scurrying, some jumping from their cars and running into the woods. Others took refuge inside the hilltop mansion of their host, beer distributor Joseph Barbara. More than sixty mobsters were eventually rounded up and identified, many flush with wads of cash. The roster included figures from the Mafia’s hall of fame: Joseph Bonanno, Joseph Profaci, and Vito Genovese. The FBI did nothing.

Two years later, on December 8, 1959, a larger group gathered closer to Boston, in Worcester, Massachusetts. The estimated 150 Mafia figures snuck into the city, assembled at a downtown hotel, held all-night meetings, and then slipped away at dawn before any significant detection could occur. The news media and many experts in crime called these assemblies proof of a national criminal enterprise, an “invisible government” that was meeting to set policy and solve disputes. But Hoover dismissed it as hype and media sensationalism.

Only after Robert F. Kennedy became US attorney general in 1960 did the FBI, slowly but steadily, move to take on the so-called enemy within. By the time of the historic public testimony of Mafia informant Joseph Valachi during congressional hearings in 1963, the FBI was officially catching up. In cities around the country special FBI units were created to focus on La Cosa Nostra. In Boston Dennis Condon and Paul Rico were among the handful of agents picked to staff the city’s first-ever Organized Crime Squad.

The agents hit the street trying to figure out the scope and power of the New England Mafia underboss Gennaro J. Angiulo, while Kennedy’s Justice Department in Washington, DC, worked to beef up the legal tools available in the new national war.

In 1961 Congress had passed legislation, at Kennedy’s behest, that elevated much of the Mafia’s criminal activity to federal status. Interstate travel in aid of racketeering, known as ITAR, now came under federal jurisdiction, meaning that the previously local crimes of extortion, bribery, gambling, and the interstate movement of gambling paraphernalia were now within federal reach.

Later on, in 1968, Congress passed the Omnibus Crime Control and Safe Streets Act. The act’s Title III set up procedures to obtain court approval for the use of electronic surveillance against mobsters. The new legislation signaled a relaxation in privacy rights, but the government viewed it as necessary, as the kind of trade-off between personal liberty and state power that had to be allowed, it was argued, if police agencies were to have a fighting chance in their efforts to break open conspiracies like the Mafia’s. Eventually the FBI put to stunningly good use the so-called Title III bugs in a series of major cases that toppled Mafia leaders in many cities in the United States, including Boston.

In 1970 Congress passed a law that eventually became the government’s most powerful weapon against organized crime. The Racketeering Influenced and Corrupt Organizations Act, known simply as RICO, would be used in nearly every major prosecution against the Mafia during the 1980s. For the first time RICO made operating a criminal racket a major federal criminal offense carrying huge prison sentences. If the government could prove a pattern of racketeering—that is, show that the mobster was involved in several existing state and federal offenses—then the heavy RICO sanctions kicked in. The RICO penalties were not something mobsters took lightly. Instead of the softer sentencing that often accompanied a separate conviction for gambling or loan sharking, the government began to win terms of twenty years and more.

Finally, the organized crime strike forces created during the 1970s quickly assumed command in the anti-Mafia crusade. The commonsense idea behind the regional strike forces was to pool the resources of the various law enforcement agencies, such as the FBI, the Internal Revenue Service, and the Drug Enforcement Agency, along with local police agencies. The representatives from the different agencies then joined with federal prosecutors as a team in an organized, multipronged attack against their specific target, the Mafia.

But for all the statutory enhancements, the anti-Mafia crusade was still going to be won or lost in the streets, and the best tool FBI agents possessed on that front was the criminal informant. “The way you solve crime, 99 percent of it is when people tell you what happened,” John Connolly once explained in a Boston radio interview. “I mean, every director of the FBI has said that informants are our most important resource.”


“Without informants, we’re nothing,” Clarence M. Kelley said after being named the new FBI director following J. Edgar Hoover’s death in 1972. The reason was simple: the police cannot be everywhere, and when investigators look to solve crimes, they do not possess unchecked power to search and interrogate suspects and citizens. In a bid to fill in intelligence gaps, a police agency finds that informants are the essential tool—the eyes and ears of the police. Police agencies’ reliance on informants developed as a partial solution to limitations on police power in the United States.

Like every FBI agent back in the 1970s, John Connolly knew full well the enormous value the bureau placed on cultivating informants. The message was drummed into rookie agents’ training at the FBI Academy in Quantico, Virginia: develop informants and win prestige. Later on, agents at work in the field saw that informant handlers were regarded as rainmakers. The FBI’s own manual reinforced in no uncertain terms a handler’s high-class status: working informants was the ultimate job—a “source of great satisfaction because of the accomplishments which are obtained as a result of their successful operation.” In fact, compared to the numbingly dry prose of the rest of the FBI’s lengthy Manual of Investigative Operations and Guidelines (MIOG), the dramatic language used to cheer on agents regarding informants borders on the breathless. Operating informants, the manual proclaimed, “demands more of an agent than almost any other investigative activity. An agent’s judgment, skill, resourcefulness, and patience are tested constantly.” The work required “dedication and ingenuity. The success each agent enjoys normally depends on the strength of the agent’s personality and resourcefulness.” So not every agent had the knack for it, but an agent who established a reputation as a handler could achieve several aims simultaneously: advance an FBI investigation, impress the bosses, and dramatically shift upward the trajectory of his own status. In training agents and in fieldwork the FBI culture made it clear that the working of informants was center stage.

Just about the only cautionary note amid the froth in the manual reflects longtime director J. Edgar Hoover’s obsession with the bureau’s public image. FBI agents, above all else, were never to shame the FBI, a commandment that covered their work with criminal informants. FBI handlers were not to sponsor an informant until they were “convinced that the potential informant [could] be operated without danger of embarrassment.”

In early 1976 Bulger reported to Connolly about business meetings between the Winter Hill gang and the Mafia’s Larry Zannino and Joe Russo. In March 1976 Bulger reported that underboss Angiulo had sent an emissary to Winter Hill in Somerville “in an attempt to establish contact with Stevie Flemmi.” The continued Mafia courtship of Flemmi was good for relations between the two criminal outfits—and good for the FBI. Bulger added that there was word that gang leader Howie Winter was going to meet with Angiulo and then godfather Patriarca, “to create a better relationship.” Later in 1976 Bulger told Connolly about the betting lines his gang and the Mafia had agreed to so that bookmakers for the respective organizations were working in sync.

Flemmi served a key role in all of the Bulger-Connolly meetings, given his easy access to Angiulo, Zannino, and the rest of the Mafia crew. Flemmi passed along what he picked up to Bulger, who would then pass it along to Connolly. Bulger’s reports were flavored with underworld tidbits—who was meeting with whom, who was mad at whom, who wanted to whack whom. For example, he told Connolly that a senior Mafia associate had faked a heart attack to avoid a federal grand jury subpoena. In April 1976 Bulger passed along a tip about a murder in an attempt to direct attention away from an enforcer who worked for him, Nick Femia. Bulger told Connolly: “Nick Femia had nothing to do with the hit of Patsy Fabiano.” Despite his earlier insistence that he would never inform about the Irish, Bulger regularly reported to Connolly about the jockeying of various Irish gangsters in his own South Boston.

All of this information was helpful, though it wasn’t as if Bulger’s inside track was going to topple the House of Angiulo. Most of it amounted to underworld gossip, and it was often flat-out self-serving. Often the reliability was questionable, but Connolly did not challenge it. Instead, just as Rico had before him, he filed reports that served to divert suspicion away from Bulger and his gang.

▪ ▪ ▪

The older agents Paul Rico and Dennis Condon belonged to the city’s first generation of FBI Mafia fighters, and they, along with their counterparts in every major US city, had worked feverishly in the late 1960s to turn around the bureau’s ignorance about all things Mafia. These agents had been instructed to get information—and to get it fast. One of the best techniques had proved to be electronic surveillance—even if the use of “gypsy wires” had required agents to bend the rules of law or even break them.

In cities around the country agents had burglarized the offices of local mobsters to install microphones, often crude devices planted behind a desk or a radiator with the wires, hidden as best they could, snaking out to a nearby location where agents secretly recorded the mobsters’ conversations. In Chicago the bug agents secretly installed in a tailor’s shop used by mobster Sam Giancana operated for five years, from 1959 to 1964. In Providence, Rhode Island, agents made secret recordings of the New England godfather Raymond Patriarca. In Boston agents Condon and Rico were part of a crew that secretly bugged the basement office of Jay’s Lounge, a Tremont Street nightclub where underboss Gennaro Angiulo often conducted Mafia business.

The FBI was not above engaging in dirty tricks—some silly, some far worse—in those hectic days of catch-up. In New York City agents one night grew tired of following a mob figure who’d picked up two women and was seen heading for a motel. The agents, wanting to go home, let the air out of the subject’s tires, hoping that would keep him in place for a while. There were also stories about agents who rattled suspected mobsters by visiting and questioning their friends and family; the aggressive, full-court press may have been designed to gather information, but it was also used to harass the targets.

Far more serious was an incident in Youngstown, Ohio: FBI agents monitoring their makeshift bug picked up Mafia talk about a plan to kill the one FBI agent the mobsters most disliked. In short order, and with Hoover’s approval, about twenty FBI agents, the toughest batch that could be assembled from nearby offices, were sent to Youngstown for a private audience with the Mafia boss. The agents crashed into the mafioso’s penthouse, trashed the place, and issued a warning that considering harm to an agent was truly unwise.

These were some of the FBI tactics of the time—before the 1968 passage of federal legislation authorizing court-approved electronic surveillance. None of the information obtained during these warrantless break-ins and bug installations could be used against the mobsters in court, but the bugs provided a windfall of intelligence that put the FBI on a fast track to closing its information gap. Eventually the FBI drew up a list of twenty-six US cities that were identified from then on as “LCN cities.” Among those cities was Boston.

The whole premise of the top-echelon informant program rested on the bureau’s understanding—even acceptance—that its informants were active in crime. It was what made them top-echelon informants: they were criminals with access to the LCN. Bulger’s gambling and loan sharking constituted the threshold crimes that the FBI was generally aware of going into the deal, eyes wide open. The challenge was, what about other crimes? Then what?

In the late 1950s the FBI had developed a set of regulations for the development and handling of informants. Over the years the regulations were revised and refined, most notably in the late 1970s when US Attorney General Edward H. Levi crafted for the Justice Department a series of informant guidelines that the FBI incorporated into its manual of operations. By decade’s end the FBI was reporting that it had 2,847 active informants on board in its fifty-nine field offices, an unknown number of them serving in the hot-ticket top-echelon category.

For handlers the guidelines were the bureau’s soup-to-nuts primer. For example, when developing an informant, an agent was required to conduct a suitability review to assess the informant’s reliability and motive. Motivation could vary: money or revenge or the competitive edge against other gangsters. If the FBI succeeded in taking down the underworld competition, an informant obviously stood to gain.

There was also a section on the admonishments an FBI handler was required to convey regularly to his informants—warnings intended to prevent an informant’s deal from softening into a cozy, protective cover. The informant was not to consider himself an employee of the FBI or to expect the FBI to protect him from arrest or prosecution for crimes he committed on his own time. Furthermore, the informant was warned against committing any acts of violence and was not to plan or initiate a crime.

The regulations also outlined controls intended to keep the agent from being compromised or, worse, corrupted. The safety checks were an acknowledgment of the danger and temptations inherent in having agents team up with criminals. Provisions emphasized the “special care” that had to be exercised “to carefully evaluate and closely supervise” the use of informants, in large measure to ensure that “the government itself does not become a violator of the law.” In an effort to keep the deal on track, an alternate FBI agent was to be assigned to work alongside the primary handler in managing the informant. To ensure that the FBI was keeping the upper hand, the handler’s squad supervisor was required to meet with the informant periodically to assess the bump and grind going on between the informant and his FBI handler. The informant’s reports were to be tested constantly for accuracy and quality. Meanwhile, agents were barred from socializing with their informants or having any business ties with them. The exchange of gifts between agents and informants was prohibited.

Taken as a whole, the regulations on paper seemed fairly airtight, but they also provided plenty of wiggle room. Even though the regulations stipulated that FBI informants could not commit any crimes, another section allowed for the “authorization” of an informant to break the law when “the FBI determines that such participation is necessary to obtain information needed for purposes of federal prosecution.” Though the guidelines discouraged use of this escape clause, the discretion to permit criminal activity rested with FBI agents in the field, agents like John Connolly, Paul Rico, and Dennis Condon. There was little oversight from FBI headquarters in Washington and no requirement that the bureau consult with anyone outside the FBI—namely, Justice Department lawyers—to review the wisdom of authorizing a particular crime. It was the FBI’s private business, an in-house matter. Deferring to the FBI, Levi and other Justice Department officials had agreed there was no other way if the FBI was going to fulfill its “sacred promise” of protecting an informant’s confidentiality. To seek outside review was to risk exposing an informant’s identity, and informants, according to the guidelines, were told right from the start “that the FBI will take all possible steps to maintain the full confidentiality of the informant’s relationship with the FBI.”

It was a pledge right down John Connolly’s alley, an institutional version of the loyalty oath taken on the streets of Southie: you never turn your back on a friend, and you always keep your word. But Southie was not the FBI. Even if field agents possessed the power to give informants room to move in the underworld, the guidelines nonetheless required that agents consult the Justice Department if they learned that their informants were committing unauthorized crimes that had nothing to do with their deal with the FBI—particularly crimes of violence. “Under no circumstance shall the FBI take any action to conceal a crime by one of its informants.” This commandment was regarded as one of the guidelines’ core principles. Getting word of a crime, the FBI had some choices. It could report the criminal activity to another police agency for possible investigation. Or it could consult with federal prosecutors and together consider whether the extracurricular criminal activity was worth tolerating given the informant’s high value. But something had to be done; some assessment of the informant’s status had to be made, a review that required outside ventilation of the FBI’s usually exclusive and secret domain.

But the rules were only as good as the agents abiding by them, and in Boston Paul Rico had already shown how the rules could be exploited or even ignored. It was as if the Boston agents focused on another section tailored to their personal styles: “The success of the Top Echelon Criminal Program depends on a dynamic and imaginative approach.” If need be, the Boston agents concluded, the rest of the guidelines could be treated as a nuisance.

▪ ▪ ▪

Boston, of course, wasn’t alone. Street agents everywhere learned to bob and weave their way through the thicket of rules, at once trying to honor them and also cut their informants as much slack as possible, all in the name of keeping the flow of intelligence uninterrupted. Given law enforcement’s own laws of gravity, gaps opened up between theory and real-world application. During the 1970s the FBI botched the handling of an informant inside the Ku Klux Klan. The klansman, Gary Thomas Rowe, was said to have committed a number of crimes, including a murder, while working as an FBI informant—crimes the FBI knew about but had covered up to preserve Rowe’s status. The peril was always out there.

Stevie Flemmi was a good example of some of the problems inherent in the system. In 1966 Flemmi had described to the FBI in detail the severe beating he gave an underworld flunkie in a dispute over a loan-shark debt. The victim required “a hundred stitches” to his head and face, according to the FBI report that Rico wrote up about the incident. But, beyond the report, no action was taken. In 1967 Flemmi regularly told Rico about his illegal football lottery card operation—the ups and downs, when the money was good, when it was slow. In 1968 Flemmi described his loan-sharking business and how he’d put money on the street that he’d borrowed from Larry Zannino. Flemmi got the money from Zannino at an interest rate of 1 percent a week; in turn, Flemmi loaned out the money at a rate of 5 percent a week, which translated into a usurious annual rate of 260 percent. He’d even hinted strongly that he killed the Bennett brothers, but it was as if Rico covered his ears: hear no evil. After all, Rico had, on his own, not only promised Flemmi that the FBI was not going to use information about his illegal gambling and loan sharking against him but also pledged to protect Flemmi from other investigators, even if it meant breaking all the rules. It left Flemmi feeling pretty special.

Now it was John Connolly’s turn.

Connolly had finally managed to get the Green matter pushed aside in order to keep Bulger and Flemmi going when another brushfire broke out. This time two businessmen from a local vending machine company named National Melotone were complaining to the FBI about Bulger and Flemmi’s competitive business practices. In a predatory and expansive move, Bulger and Flemmi were intimidating bar and store owners in the greater Boston area, demanding that they replace Melotone’s vending machines with those from a company the two gangsters controlled. Melotone went to the FBI for help.

Melotone was right to seek an investigation. During 1976 and 1977 Flemmi, Bulger, and two associates from the Winter Hill gang had scouted locations—bars and restaurants—where their vending machines could be installed. “In South Boston, Jim was looking for locations,” Flemmi said. “And I was looking for locations in Roxbury and Dorchester.”

Bulger and Flemmi had notified “salesmen” from their company about potential sites, and the salesmen had then paid visits to the bars and restaurants to explain why each establishment ought to install their company’s vending machines. It was a fairly persuasive pitch that included the muscle of a certain kind of underworld name recognition. “They would use our names,” Flemmi said.

The Melotone matter found its way to handler John Connolly.

After huddling with Bulger, Connolly set up a meeting with the executives from Melotone to outline for the company officials the hard-core truths about pursuing a criminal case. The agent told them they could certainly go after Bulger and Flemmi; that was their legal right. But he asked them if they’d really thought the whole thing through. Did they understand what it meant to testify against the mobsters—the disruption to their lives, even the risk to their families’ safety? “He painted a very bleak picture to them,” Flemmi recalled.

Connolly also told the company men their lives might be in danger. “If they wanted to prosecute, he was willing to, you know, to prosecute us,” Flemmi recalled. “But he said that they’d have to go into the witness protection program because of who we were.”

John Connolly’s grim forecast had its desired effect. Soon, said Flemmi, “they backed off.” Connolly even worked out a compromise: he promised the executives he’d arrange for Bulger and Flemmi to concede a bit. “One location was in question,” said Flemmi. “The machine came out of the place. Their machine stayed in place… . There wasn’t any problem after that.”

No harm, no foul.

It was unorthodox, but, to Connolly, why not? He’d negotiated something akin to an out-of-court settlement. No one had gotten hurt. And if the complaint evaporated into thin air, there was nothing for the FBI to investigate. Just as important, there was no reason to conduct any kind of internal review at the Boston office of Bulger and Flemmi—and certainly no reason to bring headquarters into it. The requirement in the guidelines that an informant’s crimes be reported was not even triggered. Connolly had found a way to protect the deal.

“He didn’t want to see us get indicted,” Flemmi explained. And the FBI culture provided Connolly with the room he needed to improvise; he could talk the talk of the manual but also make up his own lines along the way.

Five months after Whitey Bulger was opened up as an FBI informant, Connolly succeeded, on February 2, 1976, in having him elevated to top-echelon status. The Boston-bred agent now had two “TEs” in hand, Bulger and Flemmi. Flemmi, once “Jack from South Boston,” became known as “Shogun.” Bulger was “Charlie.”

But cracks—small fissures, but cracks nonetheless—began to show. “Connolly fashioned himself as a very important guy,” recalled Robert Fitzpatrick, a seasoned agent who became an assistant special agent in charge (ASAC) of the Boston office in the early 1980s. Connolly always seemed to be moving around the city working people in the media, in politics, and at the office. He became the go-to guy for Red Sox tickets. On occasion he failed to make the mandatory morning sign-in. Connolly’s manner began to change, and his style became more charged. He began to operate like a salesman—skilled at feigning sincerity but uninterested in the real thing. It was the consummate skill of a great pretender, a skill that became his hallmark.

And he’d apparently outgrown his marriage. John and Marianne Connolly separated in early 1978. He promptly relocated to an apartment in Quincy just a few blocks from the beach road where he’d met with Bulger that moonlit night. The apartment was also practically across the street from the Louisburg Square condo complex where Bulger bunked with Catherine Greig, the younger of his two girlfriends. But for Connolly, Quincy was part of a journey, not a destination. He began thinking about moving back into Southie.

Fitzpatrick was one FBI manager who began having reservations. He and Bulger and Connolly had a secret meeting, a rendezvous that was part of a required, periodic supervisory check of an FBI handler and informant.

“I let him bullshit,” recalled Fitzpatrick about how Bulger immediately took control of the session. Bulger talked about his weight lifting, the good shape he kept himself in.

“He did a lot of talking. He did a lot of bragging—what I would consider bragging—about how strong he was, what he was doing in prison. He told me about his background. We talked about Southie. And generally speaking, it was my impression that he was trying to impress me.”

After the meeting Connolly told his FBI boss, “Isn’t he a great fuckin’ guy?” Fitzpatrick never forgot agent Connolly’s line. Bulger—the reputed killer, loan shark, and drug trafficker—a great fuckin’ guy? Fitzpatrick blanched.

▪ ▪ ▪

In an office where some agents had their doubts, managers took comfort in the December 1977 promotion of another agent to oversee Connolly. The new supervisor of the Organized Crime Squad, veteran agent John Morris, was viewed as a good match for the savvy street agent, a straight-arrow supervisor who could serve as counterpoint.

The two paired off like an odd couple. Connolly was gregarious, tall, and dashing. Morris, a man of midwestern origins, was quiet and plain looking. Connolly was a free man moving about the town; Morris was married, with a family. He lived in the suburbs, often commuted to work with Dennis Condon, and was considered a smart, capable manager whose paperwork was thorough and of high quality.

But over time Morris would himself turn out to be the polar opposite of a role model. The FBI brass had made a horrible mistake. The intense, thin-lipped Morris was no match for all that was brewing inside the Boston office of the FBI. The deal between Connolly and Bulger and Flemmi was going to turn out to be bigger than Morris could handle—bigger than any subsequent supervisor, or even the FBI itself, could handle.