by Dick Lehr
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 U.S. 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 secretly installed by agents 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 U.S. 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 U.S. 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 59 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 wor
th 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 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 controlled by the two gangsters. 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. He 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 Connolly failed to make the mandatory morning sign-in. His 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’ gu
y? 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.
CHAPTER FIVE
Win, Place, and Show
The third race at the Suffolk Downs racetrack was set to go according to script. The Winter Hill gangsters were standing by in Somerville in eager anticipation. Led by Howie Winter, and including associates Whitey Bulger and Stevie Flemmi, they had placed thousands of dollars in bets at both the track in East Boston and with bookmakers.
Time to sit back and smell the roses.
But something was wrong. One jockey, who’d been paid $800 to do his part, had decided to improvise. Instead of holding his horse out of the running, he’d raced hard to the end. Bets had been made, and now money had been lost. Howie Winter was not happy.
