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 This sentence would be superseded by other indictments that would keep him behind bars for the better part of the next two decades.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 # Thirteen
13. mickey’s monkey
If 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 splattere
d 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.
“You’ll do what I tell you,” Coonan said to the gang. “Or you can go out there and start your own fuckin’ crew.”
Coonan wasn’t interested in preserving the Westies as an exclusively West Side Irish operation. In fact, Jimmy didn’t even live in the neighborhood anymore. The economic realities of the modern-day underworld were such that, if the gang hoped to survive and prosper, they had to recognize that the Italians were the only game in town, plain and simple. In this regard, Coonan was determined to make the partnership work. He introduced other members of the gang to Castellano and began planning crimes with Roy DeMeo and his murderous Mafia crew in Canarsie. In Hell’s Kitchen bars like Amy’s Pub, the Madison Cocktail Lounge, and the bar of the Skyline Hotel, Coonan met with his own gang and pitched assignments, many of them murder-for-hire schemes that DeMeo’s Brooklyn crew either didn’t want or weren’t able to pull off.
It was just such a job that led Coonan, Featherstone, Jimmy McElroy, and a few other Westies to find themselves drinking at the Plaka Bar on the Upper West Side late one chilly night in November. All that afternoon and into the evening, the Westies had been hunting for a union official. In fact, they’d been trying to kill this union official for days, with no luck. Tensions were running high. Many members of the gang, including Featherstone, never wanted to take on the assignment in the first place, but now that they had, they were having a hard time finding the guy. Just that afternoon, in their frustration, they’d come perilously close to gunning down the wrong man on a crowded midtown street in broad daylight.
At the Plaka Bar, Coonan was in a dark mood. By chance, the gang had just bumped into a low-level criminal they knew named Harold “Whitey” Whitehead at the bar. Coonan hated Whitehead, who had supposedly once called his brother Jackie a “fag.” To lighten the mood, everyone, including Whitehead, went downstairs to the men’s room to smoke a joint. Coonan stood at the urinal of the cramped restroom while the others formed a circle, handing the joint around and laughing. Coonan never took his eyes off Whitehead. Then, with no warning whatsoever, he pulled out a .25-caliber Beretta, put the gun to the base of Whitehead’s skull behind his right ear and—BAM! The shot reverberated throughout the men’s room, and Whitehead went down. Coonan stood over the body, eyes ablaze. He fired two more shots into Whitehead and said, “There, you bastard. Now you can burn in hell.”
It was an incredibly stupid murder, uncharacteristic of Jimmy Coonan. The Plaka Bar was connected to a hotel, with people coming and going on a regular basis. The gang quickly dumped the body in a back stairwell (there was no time to make it do the Houdini) and, in their haste, left behind shell casings and other evidence.
Months later, Coonan and Featherstone were arrested and put on trial for the murder. It was a hectic time for the Westies. While being held for the Whitehead murder, Featherstone was charged with the homicide of Mickey Spillane, which had taken place almost two years earlier. And gang member Jimmy McElroy was on trial for another unrelated murder around the same time.
The Whitehead trial was a big media event that even appeared on the front page of the New York Times. The proceedings turned out to be something of a circus, with one witness withdrawing his sworn confession and another committing suicide instead of taking the stand. In the end, Coonan and Featherstone were found not guilty. When McElroy also beat his case in court and Featherstone was acquitted of the Spillane murder, the Manhattan district attorney’s office was stunned. Thanks to their highly skilled lawyers, the Westies had apparently beaten the rap.
All was not lost for the forces of justice, however. In an all-out effort to bring down the Westies, government prosecutors cast a broad net. They got Coonan on a gun possession charge, for which he was sentenced to four and a half years. Featherstone’s counterfeit currency charge was a federal rap; he could have gotten fifteen years, but he pled guilty to a reduced charge and got a nice deal, thanks again to his attorneys.
Even before he’d been shipped out of state to begin serving his sentence at a federal pen in Wisconsin, Featherstone had begun to have misgivings about his partnership with Coonan. The reason he’d gotten involved in manufacturing and selling counterfeit money in the first place was to create a revenue stream separate from Coonan and the Italians. Many of the gang’s younger members had begun to coalesce around Mickey, who, unlike Coonan, still lived in the neighborhood. They felt that Mickey was more devoted to the concept of the Westies as a neighborhood gang, whereas Coonan seemed content to subcontract for the guineas.
Featherstone wasn’t interested in taking over the Westies, but he was interested in making a buck and staying alive. The various trials and legal entanglements had led him to consider the fact that maybe life in the gang wasn’t worth it. He had enough neighborhood contacts that, when he got out, he could find gainful employment some other way—either with the Teamsters or in the construction trades. In federal prison, far from the old neighborhood, he began to ponder the possibility of a life beyond the Westies.
The problem was that the old neighborhood ties were still strong. Mickey’s wife of six years was back in New York with their two kids. In Hell’s Kitchen, it had always been understood that if one of the neighborhood people wound up in prison, the other gang members would look out for his family. This tradition had existed since the earliest days of the Irish Mob, but it was not honored in Mickey’s case. The disappointment and anger that Mickey felt when he and Sissy were not given their due touched off a smoldering disenchantment that would eventually infect the entire gang and bring it crashing down.
That would all come later. In the meantime, even in Coonan and Featherstone’s absence, the Westies thrived. Various no-show union jobs were controlled by the gang and doled out according to seniority. There was still loan shark and gambling money coming in on a weekly basis. In ma
ny ways, life on the West Side went on as if nothing had changed. Edna Coonan, Jimmy’s wife, was making extortion collections from the unions and other local businesses for her husband, and Sissy, Mickey’s wife, sometimes tagged along in an attempt to get her piece of the action. The Westies had certainly taken a major hit with the incarceration of their two top men, but the organization continued to function. While Jimmy and Mickey monitored their own personal interests from afar, the daily operations of the Hell’s Kitchen Irish Mob were now mostly in the hands of the women.
Sissy and Edna
In the beginning, when the early Irish gangs were still based on political-resistance sects from the Old Country, women played a vital role in the Irish American underworld. In the era of the Dead Rabbits, females like Hellcat Maggie and Sadie the Goat were notorious gang war combatants, either as warriors or as crucial suppliers of arms, medical aid, and logistical support. Women also played a significant role in the early bordello business, especially in New Orleans, where prostitution served as a lamentable though viable source of refuge for destitute immigrants during the immediate post-famine years.
For the most part, however, women were marginalized in the underworld in the same ways they were in the upperworld. Since they were unable to vote until nearly two decades into the twentieth century, they were not a factor in forging ties between the mobster and the politician, a key aspect of the Irish Mob. They did not own saloons or work on the docks, and there were no women in the ILA or Teamsters union. During the years of Prohibition, when the American underworld-at-large first began its transformation from a series of neighborhood fiefdoms into a corporate structure modeled after Wall Street, women played about as significant a role as they did on the real Wall Street.
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