by The Brothers Bulger: How They Terrorized;Corrupted Boston for a Quarter Century
In the mid-1960s, the Bear too was piling up bodies right and left. Once in 1964 he murdered an ex-con in an Uphams Corner bar and then chopped off his head. Flemmi left the headless torso in a South Boston housing project (the head was never found). In May 1964, FBI agent Condon filed a report on a conversation another one of his informants had had with Jimmy the Bear: “Flemmi told him all he wants to do now is kill people, and that it is better than hitting banks.”
Finally, Gennaro “Gerry” Angiulo, who was running the Boston Mafia as Patriarca’s underboss, held a sit-down with Jimmy the Bear inside an FBI-bugged barroom on Tremont Street. From now on, Angiulo told him, Patriarca—“the Man,” as he was called—would have to approve each of his hits, personally, just as he did with Barboza.
“The Man says that you don’t use common sense when it comes to killing people,” Angiulo lectured. “Jimmy, you don’t kill somebody just because you have an argument with him.”
FBI agent Rico followed the bloodletting closely. Hoover’s newfound obsession with the Mafia meant the agents had carte blanche to cut deals with anyone who could help them achieve their mission of destroying Italian organized crime.
For any criminal who could provide the FBI with information about the Mafia, no favor was too great. Buddy McLean, for example, became one of Rico’s most valuable informants. In 1964, Ronnie Dermody, one of Whitey’s old bank-robbing crew, was released from prison and fell in with the McLaughlins. Gunning for the Winter Hill Gang boss, one night Dermody wounded a civilian he had mistaken for Buddy. As he fled, Dermody was positively identified by Winter Hill hoodlums. In a panic, knowing that he was now marked for death, Dermody called Rico to arrange his surrender to police. When Dermody arrived at the agreed-upon spot, a few blocks from Rico’s Belmont home, he was met not by FBI agents but by McLean, who shot him dead on the spot. It went into police files as another “unsolved” murder.
Rico couldn’t recruit Mafia members themselves as informants, because they were the target, so he focused instead on cultivating sources who associated with the Mafia but who had not been inducted into La Cosa Nostra.
In March 1965, Rico wanted to flip Jimmy the Bear. Rico didn’t care how many thugs Flemmi killed, as long as he could feed the FBI information on the Mafia. But even as Rico tried to recruit him, Flemmi was stalking his next victim, a smalltime hood named Edward “Teddy” Deegan. It was the murder of this minor figure that would come to symbolize the corruption in the Boston FBI office.
At the time, though, it was just another hit in the ongoing war. After getting an okay from Providence, a plan to eliminate Deegan had been quickly hatched. One of Deegan’s friends would tell him about a bank burglary in Chelsea, and he’d meet up with several guys from the Ebb Tide, a Mafia gin mill on Revere Beach. Flemmi’s shooting party would include Joe Barboza. Once they got Deegan into the alley, they would open fire.
It seemed like a simple assignment. But the murder would quickly involve the FBI in a cover-up, followed by perjured testimony, and finally the railroading of four innocent men to prison for more than thirty years for a crime they did not commit. And thirty-five years later, the murder of Teddy Deegan would lead to a congressional investigation of corruption in the Boston office of the FBI. It was that probe that would cost Billy Bulger his job as the president of the University of Massachusetts, even though neither he nor Whitey had anything to do with the Deegan murder. Whitey, in fact, was still a few days from being released from Leavenworth when the FBI first got word that Deegan was going to be hit.
On March 10, 1965, Rico filed a report quoting an informant as saying that Jimmy Flemmi was going to murder Deegan and that “a dry run has already been made and that a close associate of Deegan’s has agreed to set him up.”
Two days later, despite their knowledge of the impending murder of Deegan, the Boston FBI office approved Jimmy the Bear as an informant, and assigned him to the agent who’d recruited him, H. Paul Rico. That evening, Teddy Deegan was shot to death by Jimmy Flemmi and Joe Barboza, among others, in an alley in Chelsea.
Within hours, J. Edgar Hoover had a memo from the Boston field office on his desk accurately identifying all the killers, the real killers, as opposed to the four innocent men who would be convicted of the crime on the false testimony of Barboza in 1968. For the FBI, it was more important to keep Flemmi, and later Barboza, on the street as informers than it was to prevent the framing of innocent men. In fact, the railroading of the four men served two purposes for the FBI—it would enable their informants to escape conviction for a murder they had committed, and it would also remove several Mafia soldiers or affiliates from the scene that the FBI had not been able to eliminate in a legal manner.
H. Paul Rico quickly became one of J. Edgar Hoover’s pets. Perhaps once a year, he would fly to Washington and pick up an award for meritorious service, along with a small cash bonus, after which he would receive the ultimate honor for an FBI agent—having his picture taken with the director and Clyde Tolson, Hoover’s top aide and reputed homosexual lover. The photos would be given prominent play in the Boston papers, especially the Hearst tabloid, the Record American.
Whitey was released from prison in March 1965, a few days after Teddy Deegan’s murder. He moved back in with his mother in the projects, and quickly began dating a twenty-six-year-old single mother of four, Theresa Stanley, who would remain his most significant female companion until his final flight in 1994. The rest of the city’s underworld might have been convulsed in a bloody gang war, but in Southie, nothing much had changed during Whitey’s nine-year stint in prison. Organized crime still involved mostly truck hijackings, smalltime gambling, and barroom shakedowns.
As Whitey readjusted to life on the outside, the Irish Gang War came to an end with the October 1965 murder of Winter Hill boss Buddy McLean, and then the 1966 slayings of the last two major McLaughlin gang associates, the brothers Connie and Steve Hughes.
Whitey, meanwhile, was providing muscle for Donnie Killeen, the fading top dog in Southie, who operated out of the Transit Café in the Lower End. Whitey’s prospects for advancement in the underworld appeared uncertain enough that he decided to get “on the city”—he was hired as a “courthouse custodian” in September 1967. Records at the Boston Retirement Board indicate that although Whitey supposedly lived with his mother on Logan Way, he listed Billy’s address—828 East Third Street—as his own. Will McDonough later bragged that he, not Billy, had gotten Whitey the job, because at the time Billy lacked “the clout” to obtain even a janitor’s job for his brother.
His starting pay was $76 a week.
The job was, in essence, a no-show. Whitey appeared at the courthouse only on payday. Which left him plenty of time to worry about the threats posed to Killeen and himself both by “the kids” in Southie, and by two ambitious hoods from outside the Town who saw in the disarray across the bridge an opportunity to expand their own rackets.
The two outsiders were Frank Salemme and Stevie Flemmi, Jimmy the Bear’s younger brother. Through his brother, Stevie had gotten to know FBI agent H. Paul Rico, and as Jimmy succumbed to the late 1960s lure of drugs, Rico sought out Stevie more and more often for reliable information. Unlike the Bear, who only cared about hits and parties, Stevie was a businessman, always out hustling, perhaps because he had two families to support, with at least six children by two women. At various points, he owned a real estate business, a garage, a variety store, and he even bought a funeral home in Roxbury, where he stored his fleet of vehicles. He too was a killer—in 1967, with some help from his friends, chief among them Salemme, he eliminated all three of the Bennett brothers, who had given him his start in organized crime.
By 1967, Flemmi was resisting overtures to become a made member of the Mafia, but he had no such qualms about being made by Rico as a paid FBI informant. He went into the files as “Top Echelon,” which meant that his information was considered highly reliable. Stevie had his businesses, and the FBI, and Salemme had garages in Roxb
ury, and now they were just about ready to make their move in Southie.
But then Whitey got lucky. The feds had flipped a smalltime hoodlum who was willing to testify against both Salemme and Flemmi. He would put them together on the murder of the last of the Bennett brothers, Billy, and he would also testify that he had seen them preparing the bomb that had blown up the car that belonged to Joe Barboza’s lawyer.
By now, though, the FBI’s rogue agents in Boston had no intention of allowing Stevie Flemmi to be taken off the board. He was simply too valuable, both as an informant and as a general go-to guy, always ready to perform a favor for his FBI pals. When Rico was gunning for the McLaughlins, Flemmi had provided him with a throwdown—an untraceable firearm that Rico could have planted on any of the Charlestown mobsters if he had ever gotten the opportunity to gun down any of them in cold blood while they were unarmed. With a throwdown on the body, Rico would have been able to plausibly claim he had acted in self-defense. After Georgie’s older brother Edward “Punchy” McLaughlin was recorded in 1965 on an illegal FBI wiretap—a “gypsy wire”—describing Rico and Hoover as “fags,” it was Flemmi (and Salemme) whom Rico sought out with the address where Punchy was hiding out in Canton. A few days later, they killed Punchy as he boarded a bus. Other favors were more mundane. When Rico smashed up his FBI motor pool car during business hours at the Suffolk Downs racetrack, it was repaired at Salemme’s garage, free of charge.
So Rico owed them both. And in September 1969, Stevie and Salemme met with Rico at dawn on Revere Beach, and Rico delivered some bad news.
“There’s going to be an indictment and you guys need to get out of town. Just get out of town and play it by ear.”
Which meant that, with Rico’s help, they could ride it out. So they went back to Salemme’s garage on Massachusetts Avenue, picked up a Cadillac and some untraceable license plates from one of their people at the Registry of Motor Vehicles, and started driving. In Chicago they caught a plane to Los Angeles.
Both Stevie and Frankie had more pressing concerns now than muscling into Southie. Neither of them would be a problem for Whitey Bulger ever again.
The directive to the Boston FBI office to reach out to Whitey came directly from J. Edgar Hoover himself. On June 3, 1971, the director ordered the Boston special agent in charge to “promptly advise results of your contacts” with Whitey. With the Flemmis at least temporarily out of the picture, the FBI needed fresh eyes in the underworld. But Whitey was strictly a small-timer, with no contacts in the Mafia. It seems unlikely that Hoover would have singled him out for recruitment, unless perhaps he was doing another favor for the now retired McCormack and some of his most loyal constituents, namely the Bulgers.
Whitey certainly needed assistance from someone, because he found himself in a precarious position. He and the Killeens were embroiled in an open gang war with a faction that included Paulie McGonagle, Pat Nee, and Buddy Roache, whose brother was a young cop named Mickey Roache, and whose roommate was a pint-sized, hard-drinking street tough named Jimmy Kelly, who would later become president of the Boston City Council.
Outnumbered and outgunned by the younger group, Killeen had recruited one of Flemmi’s old associates, Billy O’Sullivan, a loanshark in the Combat Zone. Killeen had also hired a hitman to murder McGonagle, but the contract assassin ended up killing his twin brother by mistake, as well as a younger McGonagle brother, as he sat in a car. In February 1971, Buddy Roache demanded a sit-down with Whitey and O’Sullivan, during which he informed them he was going to “take out” Killeen.
“A violent argument ensued,” Condon wrote later that year, and O’Sullivan ended up shooting Roache, paralyzing him. After that, the McGonagles were still more determined to even the score, and Whitey began taking extraordinary precautions. O’Sullivan didn’t, and one Saturday night in March 1971, after returning from dinner with his wife, he was walking down Savin Hill Avenue when he was approached by several McGonagle hoods. He saw them coming and started running for a vacant lot across the street. He never made it. They shot him dead.
As soon as the memo from Hoover arrived, FBI agent Condon was assigned to reach out to Whitey. It was a task that once would have been handled by Whitey’s old friend H. Paul Rico, but Rico had been transferred, at his own request, to the Miami office. After Condon and Whitey sat down in July 1971, Condon filed the first of hundreds of reports on Whitey’s underworld observations that various Boston agents would write during the next twenty years.
That first report ran more than two single-spaced pages, and described the South Boston underworld landscape, or at least Whitey’s version of it, at some length. But when Condon pitched him on becoming a regular FBI informant, Whitey initially rebuffed him. Condon wrote that he was too “preoccupied” with his own survival to work for the feds. Whitey said both he and Donnie Killeen had become “convinced that if they did not make a move, they would be eliminated.”
Whitey had a plan, but it was one he couldn’t share with the FBI or Killeen. He would reach out to the top non-Mafia gang in Boston—the Winter Hill Gang in Somerville. It was Buddy McLean’s old crew, now run by Howie Winter, a career criminal who was six months older than Whitey. In later years, some journalists assumed that the gang took its name from its leader’s surname, but it was just a coincidence. Ethnically, it was a mix of mostly Irish and Italians, and after the years of bloody conflict against the McLaughlins, “the Hill,” as it was known, could hold its own against anyone, including the local Mafia. Whitey had to be careful, because Winter was tight with the McGonagles, and also because his assistance would come with a price tag attached. But Whitey had no choice if he wanted to survive.
Whitey journeyed to Chandler’s, the new restaurant on Columbus Avenue in the South End that Howie Winter was now using as the Hill’s headquarters in the city. There, Whitey told Howie Winter that there was no need for further bloodshed in South Boston. Once Killeen was gone, Whitey explained, the Southie gang war would be over. As part of the deal, it would naturally be Whitey’s job to dispose of his boss.
May 13, 1972, was a Saturday, and it was the fourth birthday of Donnie Killeen’s youngest son, Greg. The party was in the Killeens’ new suburban home in Framingham, and Greg Killeen’s big present from his father was a toy fire engine. Shortly after 9:00 p.m., with the sun safely down, Donnie went outside to his 1971 Chevrolet Nova, saying he was going to buy a newspaper.
As Donnie climbed into his car, the Globe reported, “Several men charged the car, rammed a submachine gun into the driver’s side, and fired 16 bullets.”
Killeen had seen them coming, and died reaching into the glove compartment for a .38-caliber pistol, which police later found on the front seat, under his body.
The next day, Donnie’s sole surviving brother was walking hurriedly along the street in Southie when a car pulled up alongside him. Whitey rolled down the window and told him, “You’re out. No more warnings.”
On Monday, the last of the Killeens called an unprecedented press conference to announce that he was retiring from the rackets, although he didn’t use that word. The Transit Café would soon be sold, and it eventually became Whitey’s headquarters, Triple O’s.
In case anyone was in doubt about the changing of the guard in Southie, the next day, at the funeral home, a large bouquet of flowers arrived for the Killeen family from a Brookline florist, collect.
The card read, “Au Revoir.”
In the spring of 1972, the movie version of The Godfather was released. The surviving Winter Hill mobsters were amused to see that Alex Petricone, one of Buddy McLean’s old pals, had a supporting role in the film, as the Jewish gangster from Las Vegas, Moe Green. Petricone had fled Somerville in 1962, moved to Hollywood, lost fifty pounds, and changed his name to Alex Rocco.
The same spring, a first novel about the Boston underworld was published to rave reviews. In The Friends of Eddie Coyle, former federal prosecutor George V. Higgins told the story of a minor hoodlum named Eddie Coyle who b
ore an uncanny resemblance to Billy O’Brien, one of Whitey’s old bank-robbing associates who had been murdered in 1967. Like Eddie Coyle, O’Brien had just been arrested on federal charges, and the papers reported that O’Brien’s associates, like the fictional Eddie Coyle’s, were concerned that he might not stand up.
O’Brien’s slaying was never solved, and neither was Eddie’s. The fictional murderer was an ex-con named Dillon, who set up the failed truck hijacking for which Coyle was to be sent back to prison. Dillon owned a bar, and was a feared freelance assassin. The fictional Dillon was also an informant, both protecting and promoting his own interests by funneling information about his underworld competition to the police.
In other words, Dillon appeared to be a prototype of the gangster that Whitey would become, although novelist Higgins, just before his death, denied that he had based his Dillon character on the real-life Whitey.
“At that time,” Higgins said, “Whitey hadn’t yet become ‘Whitey,’ if you know what I mean.”
That would soon change.
CHAPTER 4
JUST AS WHITEY BENEFITED from an event beyond his control— the Irish Gang War—so too did both he and Billy benefit from the ruinous attempt by the federal courts to integrate the Boston public school system. During the 1970s, that experiment in social engineering transformed Southie from a predominantly law-abiding working-class enclave into a festering backwater of lethal class and ethnic tensions, overlaid with drug and welfare dependency. Much of Southie’s population that could afford to fled to the suburbs, and those who remained behind came in large measure to see themselves as victims, embracing both civil and criminal disobedience against the larger society.
In many ways, it is hard to imagine the Bulgers becoming what they became without busing. The more the community was fractured, the more the brothers consolidated their power.