Black Mass

by Dick Lehr

  In the fall of 1981 Connolly filed reports from Bulger and Flemmi that predicted trouble in Halloran’s future. Bulger told Connolly the Mafia wanted Halloran “hit in the head” to eliminate him as a false witness blaming Salemme for the murder. Two months later Flemmi piggybacked the Bulger report by saying that the Mafia was hiding Salemme until Halloran could be “taken out.” The tip was a page out of Stevie Flemmi’s original playbook. Flemmi had presaged problems for Boston bookie William Bennett back in 1968, presenting the information as a tidbit he had heard on the street. But Flemmi had already murdered Bennett, rolling his dead body out of a speeding car. It was a time-honored Flemmi deception to cover his tracks and send law enforcement off after someone else.

  Halloran had a strategy too. In a no-man’s-land at the end of the line, it was time to trade up with law enforcement. He decided to strike a deal with the FBI, asking for their help in getting a reduced sentence for the Chinatown murder in exchange for his story about the party animal accountant, the Tulsa tycoon, and the killer from South Boston.

  Almost a year to the day after the North End meeting with Callahan about murdering Wheeler, Halloran talked nonstop to the FBI, from January 3 to February 19, 1982. He moved between three safe houses as the agents pressed him for corroboration that proved elusive. They had Halloran wear a wire, but that was unproductive—the wiseguys always seemed to know when he was coming. They demanded a polygraph, which Halloran refused. The Halloran debriefing became a stalemate, with agents believing his basic story but demanding more proof than Halloran could provide.

  HALLORAN became part of Bulger’s bitter legacy within the FBI when agent Leo Brunnick went to the ever-approachable Morris and asked him for his “take” on Halloran’s tale. Morris instantly realized that Halloran’s story posed a dire threat to the unholy alliance with Bulger. It was against FBI policy to retain an informant who was also under investigation by the bureau. Morris quickly disparaged Halloran’s credibility.

  While Halloran dangled in the breeze and shifted from one safe house to another, Morris told Connolly that Bulger had been accused of being part of the Wheeler murder. Morris fully believed Connolly would tell Bulger about the danger to him. Although Morris knew that dire consequences could follow his tip-off, he claimed he felt they were unlikely because Halloran’s account probably wasn’t true.

  It got worse. Jeremiah O’Sullivan was the prosecutor whom pro-Halloran agents needed to get the Winter Hill snitch safely off the street. If he gave the okay, approval would become a routine matter up the line. But O’Sullivan became obdurately against giving Halloran a new identity in a new community to protect a witness with a story to tell. To him Halloran was a problem not worth having. O’Sullivan had taken a coldhearted look at the issue and decided there was simply not enough corroboration available to make a case with Halloran. Indeed, Halloran was not an easy call. It was his word against Callahan’s, and he refused to take a lie detector test. He also had little success in developing other Winter Hill cases while wearing a wire.

  But it was also clear that O’Sullivan was partially blinded by the tight nexus of considerations involved in his prosecution of the Angiulos. “Was he part of the protection of Bulger?” another prosecutor asked rhetorically. “Not consciously. He refused to give Halloran a break on a fresh murder charge without some corroboration of the story. In those circumstances, a reduced charge would be a tough one to swallow. I’m not sure what he could have done differently.”

  Yet investigators working the Wheeler case say that O’Sullivan lost sight of the danger to an informant providing sensitive information on a major case. Several agents, according to Robert Fitzpatrick, the number-two man in the Boston FBI office at the time, became convinced Halloran could be killed if he was not enrolled in the witness protection program.

  Fitzpatrick took his concerns directly to O’Sullivan but hit a brick wall. “O’Sullivan wasn’t buying Halloran,” Fitzpatrick recalled. “To him Halloran was a wanna-be hyping a story, a drunk not worth the bother. I went back at him and said, ‘Look, my guys are coming to me and saying, ‘Get him off the street. He’s in danger.’ He said, ‘We’ve talked about this, and I’ve heard what you said, and I’ll let you know.’ That means no.”

  By May 1982 Fitzpatrick felt so strongly about the danger to Halloran that he went over O’Sullivan’s head to the newly appointed U.S. attorney, William Weld. “I told him, ‘Hey, this guy could get shot. Agents are telling me about it. We need to do something.’” Years later Weld confirmed the Fitzpatrick visit. “Fitzy said to me, ‘You know, people always say there’s danger for this snitch or that snitch. They may be killed for cooperating. I’m telling you this guy—I would not want to be standing next to this guy.’” But Weld did not intervene with O’Sullivan, who had been something of a mentor to Weld when he first took the top prosecutor’s job.

  Toward the end of his debriefings Halloran learned that Whitey Bulger was an FBI informant. Panicking, Halloran suddenly felt that he had nowhere to turn, that he was in danger on the street and even at the FBI office. “This really was the gang that couldn’t shoot straight,” said Halloran’s disgusted cousin, Maureen Caton. “It just slips out one day that, ‘Oh, by the way, Bulger’s an informant.’ Forget Waco. Just look at what happened to Brian Halloran.”

  The upshot was that the unfocused and terrified Halloran was left on his own to move furtively through a hostile landscape while the two FBI squads chafed against each other over his fate. The agents who developed Halloran found themselves fighting a rearguard action against Connolly, who had dismissed Halloran’s lurid account as self-serving prattle from a dirtbag. Although the agents who sided with Halloran had some doubts about his precise role in the crimes and plots, they firmly believed that Bulger was in their sights and Halloran was their ticket. The fight quickly intensified. Connolly was accused by two agents of rifling their files about Halloran, and the exasperated Fitzpatrick was forced to secure the material in his office safe.

  In fact, Fitzpatrick recalled, Connolly never really denied looking over the shoulders of other agents compiling information on Bulger. Connolly just stuck his jaw out, saying, “Either you trust me as an agent or you don’t. He’s my guy, and I need to know what he’s up against.”

  According to Fitzpatrick, Connolly proceeded to set up an interview of Bulger and Flemmi about the Wheeler case. In a departure from standard techniques, the pair were interviewed together; as a result, investigators lost the chance to play contradictions in their accounts against each other. The interview went nowhere and was filed away.

  BY THE spring of 1982 Halloran’s life had became a daily ordeal of constantly checking the rearview mirror and looking over his shoulder. He couldn’t go home to his wife and young son because he was afraid the door would be kicked in and a machine-gun burst would kill them all. His father and an uncle paid the rent and brought the weekly groceries to his wife.

  After several weeks of lying low, with his wife in the hospital about to deliver their second son, Halloran got a call, according to his family, that his sister living near the South Boston waterfront wanted to see him. A friend drove him into Southie, a place he had been avoiding. Around 6:00 P.M., while Halloran and his friend were parked outside a restaurant, a car containing Bulger and Flemmi pulled alongside Halloran’s Datsun. There were some shouted words and then two shots rang out. Then a fusillade. Halloran staggered free of the car and fell in the street. One of the assassins raced up to him and shot him several more times. He died with twelve bullets in him from two guns. It had all the firepower and finality of a Bulger-Flemmi execution. And it even included a telltale swerve from Stevie Flemmi. He met with agent Connolly the day after the murder, and Connolly filed a fast report saying that Charlestown gangsters may have been behind Halloran’s death.

  A Boston detective at the murder scene claimed that the dying Halloran was able to identify Charlestown gangster Jimmy Flynn as his killer. Flynn had the motive, according to poli
ce, because he and Halloran were two Winter Hill gang members who never got along, particularly after Flynn learned that Halloran had ratted him out on a bank robbery. Flynn went into hiding and was not captured until two years after the murder. In fact, he was not at the murder scene. Investigators concluded that Flynn was a patsy set up to send police in the wrong direction. Halloran’s murder was a case of Bulger doing his own dirty work, a rare instance when he stepped out of the shadows to pull the trigger himself.

  Ironically, after the Halloran murder, the discord within the FBI office abated, with agents from the two squads only occasionally glaring at each other in the back of an expansive room. It was like a dysfunctional family papering over incest. An informant had been killed, and agents began to live with the embarrassment.

  At the same time the office leadership fell into a resigned torpor about Bulger. The agent in charge, Larry Sarhatt, had gone from being a new man determined to get to the bottom of Lancaster Street in 1980 to a harried boss looking forward to retirement after twenty years in the bureau.

  As one by-product of the Boston office’s effort to smooth over internal strife, upper management became permanently hobbled by the Bulger dilemma. For the most part, the managers didn’t entirely trust Connolly. But no one wanted to deal with the institutional grief involved in taking him on. Connolly might be too close to an informant, but it wasn’t worth a brawl. It happens.

  “Connolly just became a force unto himself,” Fitzpatrick said, “a vortex in a constantly changing system. He stayed put as new agents in charge came and went. And he could take care of other agents. He became the guy who could get you sports tickets. He could help you get a day off through the secretaries. He made no secret that he could help you get a job after retirement through Billy Bulger. But he just wasn’t much of an agent. He couldn’t write a report. He was no administrator. He was just this brassy bullshit artist. We enabled him to some extent. No one had the stomach for examining what he was up to. We just never came to grips with that guy.”

  But the Halloran episode lingered in Morris’s mind. Although he had rationalized his passive role in Halloran’s demise, he knew exactly what had happened. Later, during a back-channel tip-off to Bulger and Flemmi that one of their bookies was being targeted by other FBI agents, Morris felt compelled to warn the pair against murder. Stay away from the bookie, Morris said. No more bloodshed.

  Morris had reason to fear the worst. He knew what had happened to Wheeler and Halloran. And he had firsthand experience in the fate of another underworld figure who ran afoul of Bulger. Arthur “Bucky” Barrett was an expert safecracker who got caught in the no-man’s-land between the bureau and Bulger. He had pulled a daring bank heist in 1980, working with five others to rifle safety deposit boxes of $1.5 million in cash. Shortly after the robbery Morris and Connolly were put on to Barrett by Bulger. The agents approached the safecracker with an off-the-books double mission: they wanted to soften him up for Bulger with a friendly “warning” that Whitey would be looking for a cut from the bank job. And then they offered him the perilous haven of the FBI informant program if he would become a snitch. It was a mission of staggering corruption. Here were two seasoned FBI agents acting as Whitey Bulger’s emissaries on the street.

  Nevertheless, Barrett rejected the FBI overture. And even though Barrett paid much of his bank withdrawal to placate Bulger, it did not save him from being kidnapped, tortured, and dragged into the cellar of a South Boston home in 1983, never to be seen alive again.

  But Bucky Barrett was an anonymous casualty of war. He simply disappeared, and no one misses a safecracker except his wife and kids. It was Brian Halloran’s dead body on Northern Avenue that left a deep mark on agents in the Boston office. Fitzpatrick looked back on it and felt “defeated by it all. I still think about it and fight off the ghosts.”

  TULSA homicide detective Michael Huff, the first officer on the Wheeler murder scene in 1981, had learned quickly that John Callahan and the World Jai Alai business were probably behind the killing and that the Winter Hill gang was in the picture. But he could get no hard information out of Boston. Phone calls went unreturned, and conferences were canceled or rescheduled. The Massachusetts State Police told him that Winter Hill was probably involved, but Huff could not induce the FBI to help him get background information on gang members. He never heard the name Bulger until Halloran was dead.

  Callahan was the early focus for Huff and some Connecticut State Police detectives who had been chasing the accountant with the double life for several years because of the swirl of dust around the jai alai outlet in Hartford. They began looking into Callahan’s finances and the company books for irregularities that could be used to pressure him to talk about Wheeler’s death. Detectives had even gone to Switzerland to check his accounts and recent stay there. With investigators from two states rummaging through his books, Callahan became chillingly aware that he was now the last person alive who could implicate Bulger on the murder.

  The former driving force of World Jai Alai was clearly in the crosshairs. But the pursuit of Callahan as a suspect ran into the usual detour in Boston. When Callahan first came into view as a suspect in late 1981, Huff began working with the Tulsa FBI office, which sought information about Callahan’s Winter Hill associates from none other than John Morris. In response to the queries from Tulsa, Morris sent Connolly to question Callahan. A defensive Morris later argued that Connolly was the “absolutely logical choice” to ask Callahan if Winter Hill was involved in the Oklahoma murder. Not surprisingly, Connolly reported back that Callahan had no dealings with Winter Hill and that Bulger had nothing to do with the Wheeler hit. One more time Connolly said Whitey didn’t do it. Morris obligingly closed the file.

  The quick action confused Huff. He could understand there being no hard information available, but case closed? It burned him up that Wheeler’s death didn’t strike a chord in Boston. Wheeler was a “big damn guy” in his town who hired hundreds of people and gave money to good causes. Something’s wrong here, he thought. Why won’t anyone talk straight to me about a broad daylight murder of a prominent businessman whose family deserved some answers?

  Huff and his new colleagues in Connecticut did the only thing they could do—they pushed on, scratching their heads about what was going on with the bureau in Boston. Their focus shifted to the Miami outlet of World Jai Alai to develop incriminating information on Callahan. By July 1982 Huff and the other detectives felt they had gathered enough damaging financial material to pressure Callahan in person toward the end of July 1982. They headed down to Florida on August 1. But one of Callahan’s old drinking buddies, Johnny Martorano, was already there. When Huff and Connecticut detectives landed at Miami airport, John Callahan was dead in the trunk of his rented Cadillac in a garage at the same airport. The peppery Callahan, who liked drinking with wiseguys, died like one at age forty-five.

  Now there were three dead men who shared more than the grisly fate of being shot in the head and found splayed in their cars. They had all become enemies of Whitey Bulger.

  Huff had seen Callahan as the key to the Wheeler murder. But Huff, a straightforward midwesterner, felt patronized every time he came to Boston. A weak smile, a pat on the shoulder, and then the door. The only time Huff felt he was talking sense about the case was when he got together with Connecticut and Florida homicide detectives. They began to entertain dark shapeless thoughts about what was happening in Boston. But in truth, they didn’t even know who to be mad at.

  Within the FBI Connolly hung tough against all comers on Halloran. He helped set up the long-overdue interrogation of Bulger and Flemmi about Wheeler that finally took place two years after the murder. The FBI report on the meeting records a speech by Bulger. He told agents that he was only consenting to the interview so he could put all the baseless accusations to rest. He sounded like his brother Billy talking to the State House press corps. Everything was done on Bulger’s terms. He announced that he would not take a lie detector test,
and it would take a court order to get his mug shot. And that was that.

  CHAPTER ELEVEN

  Bulgertown, USA

  Julie Miskel Rakes and her husband Stephen were like a lot of other couples from the old neighborhood—family-oriented, hardworking, and determined to make their own modest way in life. They’d grown up in Southie. Julie was from the projects, just like the Bulgers and John Connolly, and her family belonged to the same parish as the Bulgers, St. Monica’s, situated at the outer boundary of the Old Harbor housing project and across a rotary from another, the Old Colony housing project.

  Though only two years apart, Julie and Stephen did not really know each other while at South Boston High School. They met later when Julie was twenty years old and Stephen was twenty-two and operating the first of his many business ventures—Stippo’s Sub and Deli. Stippo was Stephen’s nickname, and the popular corner store sold coffee, donuts, and groceries. It was open from dawn to midnight, with Stephen’s brother, sister, mother, and father all working shifts. Stephen’s father was a particularly loyal employee. Unable to sleep, he’d go over and turn on the lights at 3:00 A.M. “We used to make jokes because he opened up at three o’clock in the morning, but he didn’t have to be open until six o’clock,” Julie recalled. “But he wanted to be ready.”

  Julie began working at the store in 1977. Stephen was the owner and manager; he was in charge of ordering the stock, handling the banking, and pricing and shelving the inventory. Soon enough the couple began dating, and then, in 1978, the Rakeses and the Miskels gathered with their friends to celebrate the marriage of Julie and Stephen Rakes. It was a South Boston family affair.