by The Brothers Bulger: How They Terrorized;Corrupted Boston for a Quarter Century
Whitey’s inmate number at Alcatraz was 1428. His initial psychological evaluation described him as “very self-centered in all he does and [he] has never developed any social responsibility.”
Whitey’s three years at Alcatraz would become another topic that in later years he would never tire of bringing up. He would discuss the Rock endlessly, with whoever would listen. There were no educational classes, no rehabilitation. Inmates saw two movies per month. It was not a happy time for Whitey.
“After I left Atlanta and arrived in Alcatraz,” he wrote in his journal, “I realized I still had LSD problems—visual hallucinations and audio hallucinations—I never mentioned it to the officials or doctor—at that point I feared they may permanently commit me to a mental institution.”
Whitey did his time on the Rock in its final days—only 148 more prisoners’ names appear on the Alcatraz roster after his. His closest friend was a Native American from Oklahoma— Clarence Carnes, better known as “the Choctaw Kid.” A couple of years older than Whitey, he’d been at Alcatraz since age eighteen, the youngest prisoner ever sent to the Rock, after his conviction on murder and kidnapping charges.
As Whitey arrived at Alcatraz in 1959, the Choctaw Kid, then thirty-two, had spent almost half his life on the Rock. In later years, Whitey told stories of a prison of unimaginable horrors, and thirty years later, at the Choctaw Kid’s funeral, which he paid for, Whitey would say Carnes had saved his life.
Another of his Alcatraz pals was John Joseph O’Brien, a bank robber from Chicago with whom he had much in common. They were the same age, and both came from urban Irish political families—O’Brien’s brother became a Cook County judge. But there was, however, one major difference between Whitey and O’Brien. To protect his family’s good name, O’Brien quickly changed his name—he became known as “Barney Grogan.” His fellow inmates called him “Dirty Shirt.”
Whitey often talked about the racial tensions at Alcatraz. The blacks were segregated in Block B, and were not allowed in the shower room at the same time as the white prisoners. One day in the late 1970s, as Whitey chatted with some of his gangland associates in a restaurant in Boston, the talk turned to a state prison, MCI-Norfolk. One of Whitey’s acquaintances at the table mentioned how “tough” he thought MCI-Norfolk was.
Whitey chuckled. “You think Norfolk’s tough? I’ll tell you what was tough. Alcatraz was tough.”
Then he recounted a story about how one time a hulking black inmate had started making sexual advances to a smaller white con, sidling up behind him and telling him in graphic detail how he planned to rape him. Terrified, the white guy fashioned a scythe-type weapon in the prison shop, which he smuggled back to his cell. A couple of nights later, just before evening lockdown, the white con hid at the top of a stairwell that he knew the black inmate would soon climb.
As Whitey told it, when the black guy reached the top of the stairs, the white inmate stepped out of the shadows and swung his scythe at the black man’s neck and took off his head. The inmates listened in their cells as the head bounced down the stairs one step at a time like a bowling ball.
Solitary at Alcatraz in the Treatment Unit—TU—was another of Whitey’s favorite topics. He would tell the same stories time and again, until the eyes of his closest associates, Stevie Flemmi and Kevin Weeks, would begin to roll as he began another recounting of how the screws would strip you to your underwear and leave you in the unheated steel boxes. It wasn’t called “the cooler” for nothing. In the winter the temperature often dipped under 50 degrees and everyone soon learned to sit in such a way as to minimize bodily contact with the steel.
Whitey Thompson, another former inmate of the Rock, described Alcatraz as “the land of forgotten men,” and that was surely the way it seemed to Whitey. His father was dying, his brother had a growing family, and instead of being less than four hundred miles from Boston, as he’d been in Lewisburg, he was now more than three thousand miles away.
Billy passed the bar exam in the summer of 1961, and joined his old friend Tom Finnerty in a two-man firm at 41 Tremont Street in downtown Boston, just down Beacon Hill from the State House. Naturally much of his work involved cases at South Boston District Court, where Sonny McDonough controlled everything. In his memoirs, Billy paints a rosy, nostalgic glow on those days, with enough avuncular judges, nipping janitors, and inept burglars to populate a John Ford movie.
Nineteen sixty-two was shaping up as a big year in Massachusetts politics. In June, in response to the increasing public outcry about corruption in state government, the legislature reluctantly passed a bill establishing the Massachusetts Crime Commission, with subpoena power to conduct closed, grand-jury-like proceedings. The commission’s chairman was an old Yankee Republican lawyer from the North Shore, whom Sonny McDonough immediately dubbed “a poor man’s Cotton Mather.”
The bigger story, though, was the impending election to fill JFK’s old Senate seat. In most years, state Attorney General Eddie McCormack would have seemed a heavy favorite. But in 1962, the president’s youngest brother, Ted, age twenty-nine, was running for the seat, with the blessing of the White House.
Billy, though, would side with Eddie McCormack. He owed the McCormacks. It wasn’t just the fact that Eddie’s father, Knocko, had passed out the snow buttons to him when he was a kid, or that they were all from Southie. In the six years that Whitey had been in federal prison, Eddie’s uncle, U.S. House Speaker John McCormack, had watched out for him. In his book, Billy described the speaker as the family’s sole source of information about Whitey’s life in prison. As first the House majority leader, and then speaker, McCormack’s inquiries to the Bureau of Prisons were always answered promptly, and McCormack would relay the information back to an increasingly despondent James Bulger Sr., assuring the old man that his eldest son might someday change his ways, if only he could catch a break. McCormack was also close to J. Edgar Hoover, and when the FBI director spoke, Washington listened.
In short, the speaker had been there for the Bulgers, and now the Bulgers, or at least Billy, would be there for his nephew Eddie. The Kennedys understood, but that didn’t mean they couldn’t make a run at Billy. The approach would be made through Gerry Doherty of Charlestown, another young Boston state rep. Teddy wanted to sit down with him, Doherty told Billy, at Locke-Ober’s, by far the most expensive restaurant in Boston.
They filed in for lunch, Ted and Billy and Doherty and a few others. Everyone else in the party took their cues from Teddy and ordered light. But Billy ordered the most famous and expensive item on the menu—Lobster Savannah, which cost $10, a fabulous sum for a meal in 1962.
All through lunch as the rest of the party implored Billy to jump the McCormacks’ sinking ship, he kept shoveling it in. Finally, Gerry Doherty, the Kennedys’ embarrassed emissary, asked Billy to put down the fork long enough to at least listen to their pitch. But Teddy shook his head.
“I don’t know whether we should try to persuade him,” Teddy said to Doherty. “I know we can’t afford to keep feeding him.”
Teddy Kennedy easily defeated Eddie McCormack in the primary, despite the attorney general’s sneering comment to him in a televised debate that, “If your name were Edward Moore, your candidacy would be a joke.” Suddenly, though, in October the focus shifted from state politics to international brinkmanship, as the Soviet Union placed missiles in Cuba, within easy striking distance of the U.S. mainland. President Kennedy demanded their immediate withdrawal, the Russians refused, and a naval blockade around the island began.
For several days, the world appeared to be on the verge of nuclear war. When the crisis ended, JFK’s poll numbers soared, and not only did his brother Teddy win what had become the family’s U.S. Senate seat, but Massachusetts narrowly elected JFK’s Harvard ’39 classmate, Endicott “Chub” Peabody, as governor. His first order of business was engineering the removal of the Iron Duke as speaker. Thompson had not been cooperative during the Cuban Missile Crisis when JFK had wanted a p
ro forma resolution of support from his home state’s legislature. Among the rank-and-file reps, the years of frustration were finally boiling over, and several candidates emerged, one of whom was Michael Paul Feeney, a reclusive state rep from Hyde Park who had first been elected in 1938, and whose proudest accomplishment in politics was his two-digit license plate, 54.
Billy Bulger threw in his lot with Paul Feeney.
For some who followed Billy’s career, it would be the first example of a problem that would haunt him through the decades—an inability to judge character or talent.
“Everybody knew what a pious fraud Feeney was,” said a surviving legislative colleague. “But Billy was still right there with him.”
Feeney’s candidacy went nowhere, but Billy wouldn’t budge. It was his year of lost causes—first Eddie McCormack, then Paul Feeney. On the eve of the vote, in January 1963, he received a phone call from the lame-duck attorney general, Eddie McCormack, asking him to come down the hall to his office right away. As soon as Billy arrived at Eddie’s office, he received a call from Speaker McCormack, asking him to change his vote from Feeney to Thompson.
Billy was in a quandary. He felt he still owed the speaker, for Whitey, yet he also didn’t want to ask Feeney to release him from his commitment to support him for speaker. McCormack told him not to worry, that Feeney would release everyone when he realized his cause was hopeless. He did, and the Iron Duke was reelected speaker, much to the irritation of JFK and his new, handpicked governor.
By then, Speaker McCormack had already delivered again for Whitey. He’d been transferred out of Alcatraz in 1962, a year before it was closed down. His last stop would be Leavenworth, where he had at least a couple of visitors from Boston. One was Will McDonough, now covering the Red Sox for the Globe. On a road trip with the team to Kansas City, McDonough rented a car and drove to Leavenworth, where he promised to take care of Whitey when he was released.
“I can get you a job,” he said, and Whitey knew the kind of work Will had in mind—a patronage job somewhere. That might look good to his parole officer, but Whitey had his own plans, and they didn’t involve punching a time clock.
Billy and Mary were now having one child per year. In 1964, old Jim Bulger died, but his widow, Jean, stayed on in the apartment on Logan Way. She was waiting for her oldest son, Jimmy, to come home to her. Which he did, finally. In March 1965, almost nine years since he’d pleaded guilty to bank robbery, Whitey Bulger was released from Leavenworth and returned to Boston.
In May 1965, the Massachusetts Crime Commission issued its final, blistering report on corruption in the state.
Part III dealt with the unchecked power of organized crime, and laid much of the blame for the state’s endemic corruption on urban politicians who looked the other way.
“Until the electorates in these areas elect officials who will attack illegal gambling actively, or until there is law enforcement by a state agency, such local conditions will continue,” the report concluded. “There is little indication that such electorates will change their voting habits in the foreseeable future.”
The commission was prescient, if nothing else. Then the panel assessed just how the Mob was able to survive:
“— They exercise strong political power in some quarters; “— They use bribery and physical violence without hesitation and with little fear of detection;
“— They command unlimited funds;
“— And they have a comprehensive spy system which enables them to exercise their power effectively.”
The commission had laid out, in a few words, exactly how Whitey Bulger would rise to the pinnacle of organized crime in Boston over the next thirty years.
CHAPTER 3
AS MISERABLE AS HIS TIME IN prison was, Whitey’s enforced absence from Boston between 1956 and 1965 was the best career move he ever made, even better than hooking up with the FBI a few years later.
During the time he spent in Alcatraz and Leavenworth, the Boston underworld’s internecine gang war eliminated large numbers of the hoodlums who would have become Whitey’s competition in the decades ahead. Many were murdered, others imprisoned, while still more simply fled the area forever.
What became known as the Irish Gang War began on Labor Day weekend 1961. In Charlestown and neighboring Somerville, two predominantly Irish mobs coexisted relatively peacefully. The Somerville group, the Winter Hill Gang, was run by Buddy McLean, and the McLaughlins of Charlestown were headed up by Bernie McLaughlin, the oldest of the three brothers who gave the crew its name. As summer 1961 ended, members of both gangs were partying in Salisbury Beach, New Hampshire. The youngest of the McLaughlin brothers was drunk, as usual, and he made some unwelcome advances toward the girlfriend of a fringe member of the Somerville crew.
When Georgie McLaughlin refused to take no for an answer, he was severely beaten and dumped unconscious in front of the emergency room of a local hospital. A few days later his older brother Bernie demanded that the Winter Hill boss, Buddy McLean, turn over the guys who’d inflicted the beating on Georgie.
McLean refused. Georgie, he said, had had it coming. Bernie was not accustomed to getting no for an answer, and a few nights later the McLaughlins tried to wire a bomb to the car Buddy McLean’s wife used to drive their children to school. Such a provocation could not go unchallenged. At noon the next day, on the McLaughlins’ home turf of City Square, Charlestown, Buddy McLean shot Bernie McLaughlin in the back of the head in front of dozens of witnesses, none of whom offered to positively identify the shooter for the police.
The war was on, and before it was over, more than forty Boston hoodlums would be dead.
At the beginning of the Irish Gang War, the local Mafia watched, amused, as the Irish and their Italian allies who weren’t in La Cosa Nostra slaughtered one another. Soon, however, the Italians realized their rackets were being adversely affected by the bloodshed and the resulting public attention. Individual Mafia members found themselves forced to choose sides, and they usually threw in with the gang whose members they’d been closest to during their last stretch in prison. It was a tangled situation, ripe for exploitation, and during Whitey’s absence from the scene, a new force appeared on the local underworld scene—the Federal Bureau of Investigation. Over the next three decades, the FBI would realize its goal, practically destroying organized crime in Boston. But as it dismantled the competing criminal syndicates, the bureau’s local office too would be devastated by the ethical compromises its agents had to make, compromises that quickly degenerated into outright corruption that included subornation of perjury, bribery, and even murder.
Until 1957, J. Edgar Hoover had denied even the existence of an American Mafia. But after Robert F. Kennedy was appointed attorney general by his brother, the pressure on Hoover to deliver Mafia scalps became overwhelming. Despite the Kennedy family’s long-standing ties to organized crime, dating from the patriarch Joe’s Prohibition bootlegging to the president’s sharing of a girlfriend with Chicago mobster Sam “Momo” Giancana, Bobby despised the Mob and put the heat on the FBI to crack down. On March 14, 1961, Hoover issued a memo instructing the field offices to “infiltrate organized crime groups to the same degree that we have been able to penetrate the Communist Party and other subversive organizations.”
In Boston, that task would fall mostly to H. Paul Rico, the Belmont native and Boston College grad who knew Whitey from the old days in Bay Village. Rico’s partner was Dennis Condon, a Charlestown guy, conveniently enough. They had joined the bureau within a month of each other in 1951.
As the gang war dragged on, a couple of particularly deadly hitmen began to stand out among the crews of underworld killers stalking Boston. Their names were Joe Barboza and Vincent Flemmi (better known as “Jimmy the Bear”), and both of them became so feared that the city’s newspaper photographers, a raffish lot themselves, often attached a note to the back of their arrest photos: “NO credit on photograph!”
Barboza was a Portuguese-American, from
New Bedford, and he dreamed of being the first non-Italian to be inducted into the Mafia. But behind his back, Mafia boss Raymond Patriarca referred to him as “the nigger.”
By 1964, Patriarca insisted that all of Barboza’s hits be cleared through him. Discussions took place at his headquarters on Atwells Avenue on Federal Hill in Providence. In May 1965 the feds reported to Hoover on a conversation one of their informants had heard between Patriarca and his hitman Barboza, who wanted permission to whack an unidentified, but very hard-to-get, hoodlum whom Barboza had been tracking for months.
“He lives in a three-story house,” Barboza told Patriarca. “So what I’m gonna do is, I’m gonna break into the basement and pour gasoline all around and torch the place, after which I either get him with the smoke inhalation or I pick him off when he’s climbing out the window.”
Barboza had worked out a plan for every contingency. He would bring three shooters with him, to watch each side of the house. They would cut the telephone lines to the houses, so that the victim couldn’t call the fire department. And just in case one of the neighbors called, before setting the house on fire Barboza planned to phone in false alarms across the city to tie up every fire company.
Patriarca asked Barboza if anyone else lived in the house, and Barboza mentioned his victim’s mother.
“You’re gonna kill his mother too?” Patriarca asked. “It ain’t my fault she lives there.”
Patriarca canceled the contract.
The other top gun in the city was Jimmy “the Bear” Flemmi. Unlike Barboza, he was a Boston native, from Roxbury, and he and his younger brother Stevie both worked with an older hood named Wimpy Bennett. A third Flemmi brother, Michael, would soon join the Boston Police Department.
