In this respect, Lucky Luciano, Meyer Lansky, and other high-ranking originators of the Syndicate or the Outfit were probably right to exclude the Irish. Experience had taught these men that the corporate structure they had in mind—a Wall Street–style version of centralized power, augmented by a board of directors and a hierarchical system of accountability—would never fly with their Celtic brethren. The Irish Mob had little interest in centralized power (they didn’t trust the concept) and were therefore averse to the kind of organizational approach that might have posed a genuine threat to the Italians. Otherwise, regional Irish gangsters like Whitey Bulger might have seen the value in returning the phone call of a fellow Irish mobster like Jimmy Coonan.
As the leading underworld chieftain in the most Irish city in America, Bulger was doing just fine with things the way they were. Through his ongoing role as a dry snitch and his cozy relationship with FBI Agent John Connolly, Bulger had vanquished all comers. He ruled with a combination of murder and treachery, but also with a total mastery of a neighborhood that was viewed by many as the last bastion of working-class Irish culture in America.
Southie was a tight-knit, proud, insular community, comprised of firemen, cops, priests, school teachers, tradesman, large families, and the occasional gangster. Unlike Hell’s Kitchen, which was a melting pot neighborhood made up of every ethnicity under the sun, Southie was Irish through and through. It was the kind of neighborhood that U.S. politicians always proselytize about: self-sufficient, with a seemingly low crime rate, hegemonic voting patterns on election day, and a fierce sense of internal loyalty that held everything together.
For better or for worse, Southie’s defining moment had come in the mid-1970s when a federal district judge sought to integrate the city’s segregated school system through forced busing, touching off what came to be known as “the busing crisis.” Residents in Southie resented being ordered to take part in a highly disruptive social experiment while more affluent communities in other parts of the city were free to send their kids to all-white schools without recrimination. The racial conflagration that erupted in Southie during the busing crisis received national and even international press. Outsiders saw it as an example of American racism at its worst; Southie residents saw it as a kind of governmental assault on their liberty. They reacted defensively, battened down the hatches, and became even more insular and circumspect in their dealings with the outside world.
Whitey Bulger played a significant behind-the-scenes role in Southie’s resistance to the dictates of the federal government. He harbored teenage kids who were chased by cops for throwing rocks at buses carrying African American school kids into Southie. In addition to his reputation as the neighborhood’s protector, Whitey was believed to be the muscle behind the South Boston Marshals, an armed vigilante group whose slogan “Hell No, We Won’t Go!” became the rallying cry of the antibusing resistance. According to author Michael Patrick MacDonald, whose beautiful, heartbreaking memoir All Souls chronicles his upbringing in Southie during and after the busing years, Bulger’s reputation attained near-mythical status in the wake of the crisis.
Whitey stepped up as our protector. They said he protected us from being overrun with the drugs and gangs we’d heard about in the black neighborhoods…. He was our king, and everybody made like they were connected to him in some way…. Everyone bragged about how his uncle was tight with him, or his brother had been bailed out of jail by him, or how he’d gotten them a new pair of sneakers, or his mother a modern kitchen set. All the neighbors said they went to see Whitey when they were in trouble, whether they’d been sent eviction notices from the Boston Housing Authority or the cops were harassing their kid. Whitey was more accessible than the welfare office, the BHA, the courts, or the cops. If your life had been threatened, your mother could always visit Whitey and get him to squash a beef.
On the one hand, the neighborhood’s residents believed in Whitey’s power because they wanted to; on the other hand, anyone who ever dared to speak out against Whitey and “the boys” were intimidated into silence. “I knew there were drugs and even gangs in my neighborhood,” writes MacDonald, “but like everyone else I kept my mouth shut about that one. Whitey and the boys didn’t like ‘rats.’”
It was no small feat: After a long criminal career, a secret role as a Top Echelon informant for the FBI, and, through skillful manipulation of a major civic crisis, Bulger had come to embody the entire history of the Irish American mobster. He was a neighborhood godfather from the Old School, yet his power was not based on nostalgia; he was not relying on the reputation of past gangsters. Whitey was the real deal. He made human beings disappear. And when the bodies washed up on Carson Beach, or were found stuffed in a ten-gallon drum or appeared unceremoniously at O’Brien’s Funeral Parlor, nobody said nothin’. Whitey must have had his reasons. Because Whitey was an honorable gangster. He kept the neighborhood free from street criminals and dope peddlers and made everybody proud.
Of course it was all a lie. Bulger presided from a back office at the South Boston Liquor Mart off Old Colony Avenue. A huge green shamrock was painted on the side of the building, but it was mostly just for show. Like most gangsters, he lived life according to an inverted value system. At the same time that he claimed to be protecting the neighborhood against the ravages of drugs and random crime, Bulger oversaw an infusion of cocaine into Southie, profiting from its sale to poor people living in housing projects and to the teenage sons of single mothers. He recruited underlings from the neighborhood’s play fields and at McDonough’s Boxing Gym, where young men without fathers were especially susceptible to the appeal of the legendary neighborhood boss. Bulger promoted the underworld as if it were all about “manliness” and “togetherness,” while for him it was really about one thing: survival. Whitey’s survival.
Eventually, the mob boss of South Boston’s charade would be exposed for what it was. The public would be the last to know. The first to know was anyone who did business with the man, especially those whose last vision—before being stabbed, shot, or strangled to death—was of the cold, piercing blue eyes of Whitey Bulger.
Shadow of The Shamrock
Brian Halloran was typical of the kind of low-level, working-class schnook who circulated in the Boston underworld of the 1970s and 1980s. A hijacker, bank robber, and leg-breaker from the heyday of the Winter Hill gang, he had been a witness to the phenomenon that was Whitey Bulger. He watched with awe as the man from Southie rose from the ashes of the Boston gang wars by masterfully working the city’s levers of power. Halloran, a high school dropout with a reading disorder, had none of Whitey’s brains and finesse. Tall and hefty, with an unruly mop of jet-black hair, thick black eyebrows, and the beginnings of a double chin, he was sometimes told that he resembled Gerry Cooney—the erstwhile heavyweight contender from the 1980s known more for the sprawling manner in which he hit the canvas after a knockout than for his boxing technique. Halloran was an Irish American palooka with an easygoing manner who tread lightly in the Boston underworld, always trying to stay on Whitey’s good side. The manner in which he crossed over the line from gangster-in-good-standing to hunted animal demonstrated the perils of “doin’ business” in Boston during the Age of Bulger.
Halloran’s descent into underworld purgatory began on a night in early 1981, when he innocently headed over to the North End apartment of a guy he was looking to do business with. The guy was a certified public accountant and consultant to a number of Boston banks named John Callahan. Halloran and Callahan had met years earlier at Chandler’s, the well-known wiseguy hangout in the South End where Howie Winter, Pat Nee, Whitey Bulger, and the Italians had negotiated an end to the Boston gang wars back in the early 1970s. Callahan was a legitimate businessman from the world of high finance, but he liked to hang out with criminals—a proclivity among men of a certain type that almost always ended badly for the so-called legitimate citizen.
Halloran knew that Callahan fancied himself a “player.” Ye
ars earlier, the portly CPA had once asked the Boston gangster if he would be willing to take part in a staged robbery. Each week, said Callahan, he hauled a bag of money to the bank from his place of business, a company called World Jai Alai (WJA), which was basically a front for a hugely profitable sports betting enterprise. Callahan’s plan was that Halloran would rob him at gunpoint as he transported the money pouch to a Brink’s truck, and then afterward they would split the bread. The bogus robbery never took place, but it was enough for Halloran to realize that John Callahan was not the upstanding citizen his bank employers, family, and friends believed him to be.
Callahan’s latest proposition also involved WJA. A sport of Basque and Spanish origin that somewhat resembles racquetball, jai alai is played with a long banana-shaped scoop used to hurl a rubber ball within an enclosed court known as a “fronton.” The game is hugely popular among both Latin and American fans and, thanks to WJA, became a major source of underworld betting in the 1980s. WJA owned frontons and sponsored leagues in Connecticut and Florida, where the company’s director of security was none other than H. Paul Rico, the former Boston FBI agent who played a nefarious role in the early Boston gang wars before he retired and moved to South Florida.
Brian Halloran knew all about WJA, and so he was not surprised when Callahan called and asked him to come by to discuss an important criminal matter relating to the company. Halloran was surprised, however, when he walked into Callahan’s North End loft and came face to face with Whitey Bulger and his partner Steve “the Rifleman” Flemmi. Halloran knew that Bulger and Flemmi were partners in WJA, which had proven to be a lucrative racket for all parties concerned, but he had not been told they would be in attendance tonight.
For reasons that weren’t entirely clear to Halloran, the Southie mob boss never seemed to like him much. As far as Halloran could tell, it had something to do with a certain Southie bookie for whom Halloran had worked as a bodyguard and chauffeur. Sometime in 1980, this bookie had fallen out of favor with Bulger, and it was made clear to Halloran that, on a specified night and at a specified time, he was to drive his boss over to the Triple O bar, a notorious bucket of blood located on West Broadway, Southie’s main thoroughfare.
On the night in question, Halloran did as he was told. He dropped his boss off, then parked his Lincoln behind the Triple O bar and waited. It wasn’t long before Halloran saw Whitey and another man dragging a heavy green trash bag down the back stairs of the bar. They dumped the bag in the Lincoln’s trunk. Halloran drove the car to the South End and left it there. Later the bookie was discovered in the trunk—dead—with a bullet hole in his head.
At Callahan’s apartment, Halloran was greeted effusively by his friend. Steve Flemmi said hello. Whitey Bulger gave Halloran his usual sideways glare. Callahan explained why they were all there. There was big trouble brewing at WJA, he said. The company had a new owner, a hard-driving CEO based in Tulsa, Oklahoma, named Roger Wheeler. Within weeks of taking over the company, Wheeler had discovered that someone was skimming one million dollars a year from the company coffers. Wheeler had announced that he planned to fire the company’s top financial officers and conduct an extensive internal audit, which was going to be disastrous for Callahan and the Boston boys.
There was only one way to deal with the problem, surmised Callahan. Brian Halloran should “take [Wheeler] out of the box.” A clean, professional hit was the only way to stop the paper trail from leading directly to Callahan’s office and to derail a likely embezzlement charge against him. The four men discussed the possible ramifications of an out-of-state murder contract, which would likely lead to a federal investigation. Bulger, who had the final say on such matters, told the others that he needed to think about it. The meeting ended, and they all went home.
Halloran, the bit player who had operated on the fringe of the underworld most of his adult life, had mixed feelings about the proposition. On the one hand, if he did the hit, he would be engaging in a high-level job with the man himself—Jimmy Blue Eyes—and that was good. On the other hand, throughout the entire one-hour meeting at Callahan’s apartment, Bulger had been giving him nasty looks, leaving Halloran feeling less than loved. As a professional hood, he knew that the closer you got to a man like Whitey, the greater the chance that you too might one day wind up in the trunk of a car with a bullet in your brain.
A week later, Halloran ran into Callahan at one of their watering holes and asked him where things stood on the Wheeler job. Callahan was a little evasive and said they were still “working out the details.” A couple weeks after that, Halloran got a call from Callahan asking him to stop by his North End apartment. With some trepidation, Halloran headed over to his buddy’s place. When he got there, Callahan told him that his services would not be needed on the “Tulsa job.” As a professional courtesy, Halloran was presented with a bag filled with $20,000 in cash. “Take the money,” said Callahan. “I never should have got you involved in the first place. My apologies.”
Halloran didn’t need to be told twice. Perennially strapped for cash, he took the money and headed out the door. In a matter of days, he blew nearly the entire twenty grand on furniture for his Quincy apartment, a long weekend in Fort Lauderdale, and the down payment on a new car for his wife.
Through the underworld grapevine, Halloran learned that the Oklahoma hit went off without him. A hit team had been dispatched from Boston. Fifty-five-year-old Roger Wheeler, the CEO of World Jai Alai, was shot in the head at close range after having just finished a round of golf at the Southern Hills Country Club in Tulsa. The man who supplied the hit team with information on Wheeler’s routine and whereabouts was H. Paul Rico, the former Boston G-man and now director of security for World Jai Alai.
Halloran would like to have been able to forget all about the Tulsa hit, but he was acutely aware that, as the only person with knowledge of the murder who wasn’t directly involved in its implementation, he was a marked man. If he needed a reminder, it came in the form of a fusillade of bullets fired in his direction from a passing car one morning, while he was dumping the trash in front of his Quincy apartment.
The small-time hood became frazzled and paranoid. With a wife and a young child, he didn’t feel he could just pack up and run. He tried to create an independent revenue stream for himself by getting involved in the drug trade. He was not only selling coke, but also was using it a fearsome rate and drinking heavily. Brian Halloran was a disaster waiting to happen.
On a rainy night in October 1981, it happened: Halloran shot and killed a Mafia-connected coke dealer at a restaurant in Chinatown. After hiding out for a month, Halloran turned himself in to the authorities. He was charged with first-degree murder and released on $50,000 bail, with the proviso that he could not leave the Boston area. Under the circumstances, he probably would have been better off hijacking a NASA spacecraft and leaving the earth’s atmosphere. The word on the street was that the Italians wanted the Irish gangster dead for having whacked one of their coke dealers. Meanwhile, Whitey Bulger and his crowd harbored the knowledge that Halloran was the only living nonparticipant capable of ratting them out for the Tulsa murder.
Given his predicament, the low-level Irish hood took what must have seemed like the only logical step—he reached out to the FBI. Desperate, facing a possible sentence of 25 years to life, he introduced himself to a veteran agent in the Boston office named Robert Fitzpatrick. Halloran told the agent that if the FBI could help him get a reduced sentence in the Chinatown murder, he had information that could help them solve a certain homicide in Oklahoma.
“Maybe,” said Fitzpatrick upon hearing Halloran’s proposition. “But first I need to know what you know.”
That night Halloran signed a statement that read, in part: “I was offered $20,000 by John Callahan to kill Roger Wheeler. Bulger and Flemmi were present at Callahan’s apartment when the offer was made. Callahan said the owner, Wheeler, discovered someone was ripping off one million dollars a year from the Jai Alai operatio
ns and was planning to fire the executives, conduct an audit, and bring in state officials to investigate.”
Agent Fitzpatrick and his partner worked Halloran like a mule. For six straight weeks, from January 3 to February 19, 1982, they pumped him for information, moving him from safe house to safe house so that his whereabouts would not be detected. They had Halloran wear a wire and circulate in the underworld, but that proved unproductive. Everywhere he went, the big Irish lug gave off the stink of desperation—the telltale aroma of a stool pigeon. When Halloran walked into the Triple O, the Mullen Club, Kelly’s Cork & Bull, or other well-known Southie watering holes, even the priests headed for the exits.
The likelihood that Brian Halloran was yakking to the Man was more than just idle chatter. Southie was the kind of neighborhood that had a mainline into many things related to city government, and it didn’t hurt at all that two prominent FBI agents were—for all intents and purposes—members of Bulger’s organization.
As Chief of the FBI’s Organized Crime Squad in Boston, John Morris was apprised of the fact that Halloran was telling tales about Bulger and Flemmi. By this time, Morris had completely fallen under the thrall of John Connolly, the brash Southie-born agent who first brought Whitey into the fold, and Bulger himself, with whom Morris and Connolly met socially on numerous occasions. The two agents were in deep with Bulger, having tipped him off about investigations and informants and, in Morris’s case, taken bribe money in the form of gratuities and cash. Morris knew full well that if other investigators in his office began to delve too deeply into Bulger’s activities, his own unethical—if not criminal—relationship with Bulger would be exposed.
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