Paddy Whacked: The Untold Story of the Irish American Gangster (70 page)

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.” Years 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 operations 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.

In a late-night bull session at the downtown FBI office, Morris told Connolly, “John, we got a problem. Brian Halloran has implicated Jim Bulger and Flemmi on the Tulsa murder. We’ve got to head this off at the pass.”

“Don’t worry,” said Connolly. “I’ll take care of it.”

Connolly immediately set up an “interview” with his two informants, Bulger and Flemmi, supposedly to explore what they knew about the Tulsa matter. After talking to the two men, Connolly filed a report stating that Halloran’s claims “could not be substantiated by the facts,” after which Morris officially closed the investigation.

Bulger and Flemmi were in the clear, and they celebrated with a wine and dinner party at Steve Flemmi’s mother’s house in Southie. The honored guests at the dinner party were agents Morris and Connolly. The two gangsters had reason to celebrate. Not only had they once again gotten away with murder, but they also now knew for sure—thanks to the FBI agents—that Brian Halloran was a rat.

Halloran’s predicament just kept getting worse. No matter which way he turned, the shadow of Whitey Bulger was upon him. He had tried to come in from the cold and deliver the top mobster in Boston to the FBI on a silver platter, and now he was in even more danger than before.

Robert Fitzpatrick, the agent with whom Halloran first established contact, was understandably concerned for his C.I.’s life. Although he did not yet know that his own agents had tipped off Bulger about Halloran, word on the street was that his informant was not long for this world. The agent approached Assistant U.S. Attorney Jeremiah O’Sullivan, whose approval Fitzpatrick needed to offer Halloran a plea-bargain deal for his cooperation and get him off the street and into protective custody.

O’Sullivan, of course, knew all about Whitey Bulger’s role as an informant; he was the one who had severed Bulger from the 1978 race-fixing case, which had resulted in convictions for every high-ranking member of the Winter Hill Gang except Bulger and Flemmi. O’Sullivan also knew that, in accordance with government policy, the FBI was not allowed to keep Bulger on as a C.I. if he was under criminal investigation. In a sense, the prosecutor was being asked to choose between Brian Halloran and Whitey Bulger—a no brainer. Instead of listening to Fitzpatrick, who was telling him that Halloran’s life was in imminent danger, O’Sullivan went with Morris and Connolly, who were telling him that Halloran was a wannabe and a drunk who knew nothing about the activities of a man like Whitey Bulger. Halloran was denied protective custody.

In May 1982, the low-level Irish hood’s official role as an informant was terminated, and he was cut loose. The FBI had chewed him up, set him up to be killed, and spit him back out on the street. He couldn’t live at home with his wife, who was pregnant with their second child, for fear that someone might bust through the door and shoot them all to death. Moving from safe house to safe house, he trusted no one and slept with a gun under his pillow.

On the night of May 11, less than a week after being dumped by the FBI, Halloran got a call from his sister, who was living near the South Boston waterfront. She wanted to see him. A friend drove him into Southie, a place he’d been avoiding for months. Around six o’clock in the evening, he and his friend were sitting in a Datsun outside a restaurant on Northern Avenue. A blue Chevy pulled alongside them. Before Halloran had time to react, a fusillade of machine-gun fire rang out. Halloran was hit; he staggered out of his car and fell in the street. One of the assassins ran up to him and shot him several more times with a pistol. Halloran died with twelve bullets in him from two different guns. His friend—an innocent bystander—was also killed.