Paddy Whacked: The Untold Story of the Irish American Gangster (64 page)

They met in a parking lot at Wollaston Beach in the shipbuilding city of Quincy, on Boston’s southern border. On a pleasant moonlit night, they sat in the front seat of Connolly’s Plymouth talking about old times and mutual concerns. Whitey, who’d recently turned forty-six, was no spring chicken. Although he was a physical fitness buff and as tough as a man could be at his age, the Boston underworld was crawling with younger, hungrier predators. Whitey’s emergence as the boss of Southie made him a marked man; if he hoped to stay alive, maintain his position, and get ahead, he would need to massage the system.

The Mafia in New England was expanding in 1975, with the Godfather Syndrome then in full flower. Connolly told Bulger that they had a mutual enemy—what the feds referred to as LCN, La Cosa Nostra. If Whitey were willing to feed him information on the Italians and help him make cases, then Connolly would help protect Bulger from his enemies; in this mutually beneficial relationship, the Irish mobster would become an official, registered informant for the FBI and in return be virtually inoculated from criminal prosecution.

“The only thing you can’t do is kill people,” Connolly told Bulger.

Whitey jumped at the deal. That very month, he signed on as a C.I. and proceeded to continue his murderous ways. In fact, Bulger’s newfound status as a protected informant likely gave him delusions of grandeur, leading him to surmise that the U.S. government, in the person of John Connolly, now had a vested interest in maintaining the fiction that he was some kind of honorable racketeer willing to help the FBI in their efforts to take down the dreaded Mafia.

Just one month after signing on as an official FBI informant, Whitey Bulger murdered Tom King. King was a former member of the Mullin Gang, now affiliated with Winter Hill, whose primary fault was that he had once whipped Bulger in a bar fight. In the back seat of a car near Carson Beach in Southie, Whitey shot King in the head. Then he and a couple of accomplices buried King’s body in a marshy area near the Neponsit River in Quincy.

Whitey’s main accomplice that day was Steve Flemmi, a savage contract killer who went by the nickname the Rifleman because he had become an expert marksman while serving as a paratrooper during the Korean War. Unbeknownst to almost everyone, Flemmi had himself been an FBI informant since 1965. Now that he and Bulger were both secretly affiliated with federal lawmen, they formed a partnership that crossed ethnic lines (Flemmi was Italian American). Over the next two decades, the duo of Bulger and Flemmi would become known as one of the most homicidal gangster partnerships in the history of the American underworld.
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The benefits of Bulger’s newfound status as a Top Echelon informant were immediately apparent. In 1977, John Connolly got wind of the fact that Bulger was one of numerous local criminals under investigation by a federal prosecutor in connection with an elaborate race-fixing scheme. A group of mobsters led by Howie Winter, boss of the Winter Hill gang, had been fixing races for years along the East Coast by paying bribes to track officials, jockeys, and horse owners. Combined with various extravagant bets placed with designated bookmakers—some of whom were in on the scam and some not—it had been a highly profitable racket. Prosecutors estimated that the Winter Hill Gang’s race-fixing scam had amassed more than $8 million in profits while operating in eight states.

A key operative in the scheme had turned canary, and more than a dozen indictments were about to come down. Connolly and his boss, John Morris, the new Chief of the FBI’s Organized Crime Squad in Boston, approached the prosecutor who was overseeing the case. They informed prosecutor Jeremiah T. O’Sullivan that two of the men about to be named in his indictment—Bulger and Flemmi—were valuable Top Echelon informants for the Bureau. Furthermore, these two informants were crucial to an impending FBI investigation that would, if all went according to plan, bring about the demise of the Mafia in Boston. Bulger and Flemmi, argued Connolly, were too valuable to sacrifice on the race-fixing case. Wasn’t there some way they could be dropped from the indictment? O’Sullivan was amenable to the idea, especially if Bulger and Flemmi were to provide information that would help bolster the charges against Howie Winter, et al.

About a month later, a racketeering indictment was returned against thirteen defendants. Bulger and Flemmi were not among them.

By the time the various trials and plea-bargaining arrangements were over, the race-fixing case resulted in the incarceration of nearly the entire upper echelon of the Winter Hill Gang. The venerable Howie Winter, the man who had helped negotiate an end to the Boston Gang Wars and saved Bulger’s life back in 1972, was sentenced to ten years. This sentence would be superseded by other indictments that would keep him behind bars for the better part of the next two decades.

Whitey Bulger was now the de facto boss of the Winter Hill Gang. For the first time in the gang’s history, their headquarters was moved out of Somerville into a garage on Lancaster Street in downtown Boston. The Lancaster Foreign Car Service became a front for Bulger’s operation. On a daily basis he, Flemmi, and others met at an office inside the garage, received payments from various bookies and loan shark customers, and planned new crimes. The garage office was strategically placed midway between the headquarters of the Boston Mafia, with whom Bulger did business, and the downtown field office of the FBI.

Up until now, the relationship between Whitey and the feds had mostly been a one-way street. Bulger had been secretly spared from criminal indictment and kept abreast of underworld developments by Connolly. Bulger had even been tipped off about a bug that was planted in his Lancaster Street headquarters by the Massachusetts State Police, who had concluded in an internal memo that “virtually every organized crime figure in the metropolitan area of Boston, including both LCN and non-LCN organized crime figures, frequent the premises and it is apparent that a considerable amount of illegal business is being conducted at the garage.” By leaking information about the bug to Bulger, Connolly effectively sabotaged the state police investigation.

Throughout history, there had rarely been a sweeter arrangement between a mobster and the law. Connolly was acting as Whitey’s Big Brother and getting little in return. But that was all about to change.

In 1981, in a daring late-night operation, the FBI planted a bug in the North End headquarters of Gennaro “Jerry” Anguilo, the Mafia boss in Boston. Angiulo was a white-haired, cantankerous mafiosi with a Napoleon complex who didn’t care much for Irishmen, especially Irish cops, whom he’d been paying off for years. “It takes a special guy to be a cop to begin with,” Angiulo once said. “Disturbed upstairs…that’s why all Irishmen are cops. They love it. Alone they’re a piece of shit. When they put on the uniform and get a little power, they start destroying everything.”

Angiulo’s big mouth eventually brought about his demise—and the demise of the entire Cosa Nostra in Boston. The bug planted inside Angiulo’s North End headquarters proved to be the centerpiece of a massive RICO case that ended with the prosecution of Jerry Angiulo, four of his brothers, and nearly a dozen others.

There has always been a difference of opinion about the extent of Whitey Bulger’s contributions in the Angiulo case. FBI agents Connolly and Morris may have puffed up Whitey’s role in an effort to enhance his stature within the Bureau. By most accounts, it worked. Although Bulger never had to testify in court and his role as an informant was never publicly acknowledged, in the upper echelons of the U.S. Justice Department, his contributions did not go unnoticed. With the Angiulo prosecutions of the mid-1980s, the FBI’s Boston office was the toast of the law enforcement community, and Bulger’s cooperation was considered by insiders to be a major coup.

For the man himself, the results were almost beyond belief. In seven short years—since climbing into bed with John Connolly and the FBI—the middle-aged mobster from South Boston had eradicated his rivals in the Winter Hill Gang, effectively taking over that organization, and presided over the fall of the Mafia in Boston. Whitey was now much more than just a wily neighborhood boss from Southie or even a major player in the Irish Mob; he was the lone man on top, king of the Beantown rackets, overseer of the city’s gambling and loan-sharking operations who could rightfully claim a piece of every act of organized crime that took place in the entire metropolitan area.

It must have looked dandy, as life on top frequently does. But already planted within the story of Bulger’s impressive rise to power were the seeds of destruction, not only for Whitey, but also for the entire Irish Mob.

Bulger may have outsmarted the Italians and scored a major victory in the ongoing battle between the dagos and the micks, but at what cost? His role as a government dry snitch and the use of informers in general was an insidious development with ominous implications for the mob. Apparently, the rules of the underworld had changed. The forces of the law were looking to infiltrate the mob and bring it down from within. If that meant garnering the cooperation of men who might previously have been viewed as beyond the pale, then so be it.

It was the 1980s, and the American underworld was heading into a new phase of paranoia and self-destruction. In places like New York and Boston, where the Irish American mobster was still a viable factor, old-time racketeers from the 1940s and 1950s hardly even recognized the menu. The daily special was a gastronomical disaster: a large helping of deceit and betrayal, with a topping of savage violence, and a side platter of dismemberment. The era of the informer had arrived, and the Irish Mob would never be the same.

CHAPTER
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Thirteen

13. mickey’s monkey

I
f the Irish American underworld of the early 1980s were a celestial constellation, the latest incarnation of the Hell’s Kitchen Irish Mob would be the dark star, an angry planet spinning out of control. Led by Coonan and Featherstone, the Westies had shot and Houdinied their way to the Mafia banquet table, but they didn’t really know what to do when they got there. They were more accustomed to being the fly in the ointment than equal partners in a corporate-style racketeering enterprise. Coke, whiskey, greed, and the ability to kill people at will and get away with it had led them to the demonic side of American gangsterism.

Although never comprised of more of than twelve to twenty members—depending on who was in or out of jail at any given time—the Westies became synonymous with the last generation of Irish in the birthplace of the Irish Mob, a mongrel community that started with the gang and spread out from there. Brothers, sisters, nieces, and nephews claimed association with the Westies even when they were not criminals themselves because the gang represented muscle, historical continuity, and a revered brand of neighborhood loyalty that supposedly ran deeper than blood.

By claiming affiliation with the Westies, some residents of Hell’s Kitchen were literally putting their lives on the line. Many of the gang’s most outlandish acts had nothing to do with racketeering or profit motive. Friends killed friends over stupid barroom arguments. People got beaten up for talking to the wrong people. Old grudges were rekindled and violently resolved in the amount of time it took to snort a half gram of Colombia’s finest. Innocent bystanders fled in horror or became part of the collateral damage. In January 1981, a well-known neighborhood gambler who interceded in a brawl between two brothers got himself tossed from one of the upper floors of a sparkling new forty-three-story apartment building. He splattered on top of a parked car on Tenth Avenue. In early 1982, Richie Ryan and longtime Westies compatriot Tommy Hess got into a beef at the 596 Club. Before it was over, Ryan pulled Hess’s pants down around his ankles, stuck a revolver up his rectum, and pulled the trigger. Patrons stampeded toward the door. By the time cops arrived, Hess was dead, and there wasn’t a witness in sight.

The fact that the gang was wild and unpredictable was terrifying, but not necessarily bad for business. “The more bodies the better,” Jimmy Coonan once said. Coonan knew that dead bodies and spontaneous acts of mayhem were calling cards for a neighborhood gang; they only enhanced its reputation. As tenement gangsters from the Old School, the Westies were merely putting their own unique spin on a tradition that had been around since the days of the original Five Points gangs, when bodies were often buried in basements and tenement walls.

Mickey Featherstone was both an instigator and a victim of the Westies’ mystique. He was the original loose cannon, a troubled Vietnam vet who had become Coonan’s enforcer and then a major player in the New York underworld who dined with the Mafia elite. He had become a legend in his own time and was sympathetically profiled by the newspaper columnist Jimmy Breslin (himself a bona fide New York character) in the
Daily News
: “Mickey Featherstone, discharged from the army after serving as a Green Beret in Vietnam, stared at his sister. His face was the wall of a funeral parlor and his eyes were looking at a log fire that was something else.”

At the age of thirty-one, with a wife and son, Featherstone had become an underworld celebrity, but he was not a happy man. By the early 1980s, he’d begun to have doubts about his role in the gang. Those doubts took root and festered while he was in the penitentiary. The circumstances that had led Mickey Featherstone to a stint in the big house were part and parcel of the Westies legend. The road to disaster started back in November 1978, a few months after Mickey and Jimmy Coonan had their sit down in Brooklyn with Paul Castellano and other high-ranking members of Cosa Nostra. Almost immediately, behind Coonan’s back, members of the gang began to complain about their new status as errand boys for the Italians. Jimmy was aware of these complaints, and he had no sympathy whatsoever.