Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

PART TWO

I do my best to protect you and I may break a
few rules, but I break them in your favor
.

RAYMOND CHANDLER,
THE BIG SLEEP

CHAPTER TEN

Murder, Inc.

Shortly after the new year arrived in 1981, Brian Halloran backed his ratty Cadillac into a space in front of the Rusty Scupper, a busy North End restaurant, and bounded upstairs to the loft apartment of his drinking buddy from the world of high finance. Accountant John Callahan had asked him to stop by to talk business, and that sounded like money to the usually strapped Halloran.

They were an odd pair that got on. Halloran, a rangy leg-breaker from the Winter Hill gang, and Callahan, a squat CPA and consultant to Boston banks, had struck up an unlikely friendship rooted in Boston’s nightlife. They had first bumped into each other in the early 1970s at Chandler’s, a wiseguy hangout in the South End controlled by Howie Winter. The extroverted Callahan liked to walk on the wild side, and that is where the scruffy Halloran lived, usually at loose ends, just getting by on the feast-or-famine cycle as an enforcer in the underworld’s brutal collection business.

Callahan talked to bankers by day and socialized with mobsters by night. Like Halloran, he took a drink and liked a good time. The wiseguys saw him as a big spender who knew how to make money and, more important, how to launder it. After hanging out at Chandler’s for a couple of years, Callahan tried connecting the corporate world with the underworld by proposing a deal that startled Halloran. One night in the mid-1970s Callahan asked Halloran if he would “rob” him as he lugged a money bag from his main place of business, a company called World Jai Alai that was a gambling cash cow. Halloran would hold him up as he walked the pouch to a Brink’s truck, and then afterward they would split the money. The phony robbery never took place, but Halloran understood that Callahan was more than a “fun” guy with a fat wallet—he was a player.

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After Halloran was buzzed into Callahan’s apartment overlooking Boston Harbor, he was surprised to see Whitey Bulger and Stevie Flemmi sitting in the living room. Callahan gave him an effusive greeting. Stevie said hello. Bulger said nothing. Whitey didn’t like Halloran much, and it showed. On the street Bulger’s silent treatment was seen as the kiss of death.

But Halloran was surprised only for a moment. In recent months Callahan had been bragging to him about Bulger and Flemmi wanting to be partners in the “World Jai Alai action” Callahan had carved out of the heavy-betting that accompanied a court game mostly resembling racquetball and played at “frontons” in Connecticut and Florida. To Halloran, the presence of Bulger and Flemmi signaled the deal was past the negotiating stage—and it was also now clear that Callahan was no longer just a hot-shit accountant with a party personality and banking connections. In fact, Callahan was washing money for Bulger and Flemmi, and whether Callahan realized it or not, he’d traveled a long way from the city’s financial district and now belonged to Winter Hill.

There was some strained small talk all around, and then, in a nervous patter, Callahan got right to the heart of the matter. He said a serious problem had come up at the World Jai Alai Company in the form of a new owner from Tulsa named Roger Wheeler. The hard-driving CEO from Oklahoma “had discovered something was not right.” Wheeler, he said, had figured out someone was skimming one million dollars a year from the overflowing company coffers. Now the owner planned to fire the company’s top financial officers and replace them with his own people. This Wheeler was a danger, Callahan emphasized, and Callahan feared he’d end up in jail because of the owner’s plan to conduct an extensive internal audit.

But then John Callahan also had a solution. Brian Halloran, he proposed, could “take [Wheeler] out of the box,” which was to say shoot him in the head. He said a “hit” was the only way to stop the paper trail short of his office door, the only way to end any possibility of an embezzlement charge against him. He added that Winter Hill’s seasoned hitman, Johnny Martorano, should probably get involved. Nothing beat experience. Flemmi chimed in from the couch with some much-needed skepticism: would “their friends” at World Jai Alai stand up once the police were called in? Because the prospect of coconspirators turning against Callahan was not an acceptable business risk. And the unasked question: Would Callahan himself be able to take the heat?

During the talk Bulger hung back, sitting there, watchful and listening hard, not saying a word. By this time he was a long way from South Boston barroom gambling and the tense days of 1972 when he worried about being killed by the Mullin gang. He’d not only risen to the top but was living on gangland’s easy street, choosing his investments from a wide variety of options. He actually had more business than he could handle, in large part because a key asset, FBI agent John Connolly, was watching his back within law enforcement.

He’d made it to the top echelon by carefully plotting his course, making full use of the extraordinary latitude he’d come to expect in running an underworld franchise that inherently had its messy moments. There’d been a number of housekeeping murders of minor figures in Southie’s underworld since he’d teamed up with the FBI in 1975, but the growing body count brought not a single knock on Bulger’s door. No sign of trouble even when the bloodletting extended to one of Stevie’s girlfriends. Debra Davis, the voluptuous twenty-six-year-old who’d been with Flemmi for seven years, was making plans to leave him. Vacationing in Acapulco, she’d fallen in love with a young Mexican entrepreneur in the olive oil and poultry business. Davis wanted marriage and, eventually, a family—impossible dreams in the Flemmi arrangement. But a breakup was not an option to the possessive Stevie, and Davis disappeared without a trace on September 17, 1981. Davis had started the day shopping with her mother, and then, after a goodbye kiss, said she had to see Flemmi. Her mother and brothers tried going to the FBI, but the agents who came around seemed more interested in learning exactly what Debra knew about Stevie than in solving her disappearance, and soon the investigation petered out. By working carefully within their violent world, Bulger and Flemmi had learned they could do anything they wanted. Playing his brand of chess first talked about with Connolly at Wollaston Beach, Bulger had become immune from everyday investigations.

The question Whitey now had to decide was how far was too far? Would a murder in Oklahoma bring too much heat? Would the FBI, through Connolly and Morris, look the other way on an execution undertaken far beyond the boundary lines of South Boston’s gritty underworld, where a periodic bloodletting was as normal as a quarterly business report on profits and losses?

Then again, why not? Bulger now assumed Connolly would help him out anywhere. Roger Wheeler may have been a multimillionaire from Tulsa with seven corporations branching into everything from oil to electronics, but as 1981 dawned over Boston, Wheeler was just another guy in Whitey Bulger’s way.

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It was a lot for Halloran to take in. And it was a lot to ask of a minor league player who had pulled a few bank robberies before catching on with Winter Hill in 1967 toward the end of the Irish gang war, a bloodbath that began when a drunken mobster insulted somebody’s girlfriend at the beach. Over the years Halloran had talked a good game but was best known for slapping around overextended sad sacks who owed shylock money. Halloran was on the second team, but Bulger still used him only to enforce loans and move cocaine—he had not killed anyone.

Halloran played a bit part, however, in the murder of one of Southie’s better-known bookies, a killing that had hammered home how dangerous Bulger could be. In April 1980 Halloran had chauffeured Louis Litif to the Triple O’s bar, located along Southie’s main thoroughfare, West Broadway.

For years Litif had been one of Bulger’s most productive bookmakers, but he had recently veered into drug dealing and, in a fatal misstep, murdered another dealer without clearing it with Bulger. After Halloran dropped Litif off, he parked the Lincoln behind the bar and waited. It wasn’t long before he saw Bulger and another man lugging a heavy green trash bag down the back stairs. They dumped the bag in the Lincoln’s trunk. Halloran drove the car to the South End and left it there. Later Litif was found in the trunk with a bullet hole in his head.

So when the subject turned to murder at Callahan’s apartment, Halloran knew it was not idle talk. But this time he would be pulling the trigger, not parking a car. He got darty-eyed, cleared his throat, and asked if there was any alternative to “hitting the guy.” This brought him one of Bulger’s patented cold glares. The hour-long meeting broke up with Bulger saying he would think about it some more, but Halloran drove away from the North End believing Roger Wheeler was a dead man.

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Wheeler had an eclectic empire that specialized in electronics through a flagship company named Telex, a manufacturer of computer terminals and tape decks. He had grown up in Massachusetts but went to school in Texas and became an electrical engineer. By the late 1970s Wheeler’s high energy and ambition got him to the point at which Telex earned $8.1 million on revenues of $86.5 million. But for several years he had been in the market for something with a higher profit margin, and he became mesmerized by the money in the gambling industry.

The father of five was a family man and a churchgoer, but he was no choirboy. He could be brusquely demanding, even imperious in the CEO kind of way. He made no bones about being drawn to gambling by its high cash flow and relatively low capital costs. He had nibbled around the edges of the industry for several years, first looking into Virginia’s Shenandoah racetrack in 1976 and a Las Vegas casino in 1977. He settled on the World Jai Alai company, with its outlets for racquetball-style betting games in Connecticut and Florida, because of an irresistible $50 million financing package that the First National Bank of Boston put together.

As it turned out, the bank had its own consulting relationship with John Callahan, and its loan provisions reflected that. Although Wheeler protested, the bank would put up the money only if he retained Callahan’s former business partner, Richard Donovan, as president of World Jai Alai. The other stipulation was that Wheeler keep former FBI agent Paul Rico as head of security.

With the rest of the deal too good to walk away from, Wheeler took the loan and bought the company. It was a coup for Callahan, as just two years before the World Jai Alai board of directors discharged him for profligate spending and underworld ties with the likes of Brian Halloran and Johnny Martorano.

Although some of the handwriting about World Jai Alai was already on the wall, Wheeler was distracted by the opportunity to finally get a gambling business and dazzled by the $5 million profit a year, a healthy 16 percent of revenue. But behind the beguiling bottom line were some disturbing dossiers on Callahan and his longtime business partner.

Nevertheless, Wheeler thought he could have it all—gambling revenue and a clean skirt. He thought his business acumen could override the “shady characters.” Gradually, however, Wheeler had second thoughts about what he had gotten into. He became fearful, according to business associates. He took some ironic solace in the large retinue of former FBI agents who worked for World Jai Alai, including the redoubtable Paul Rico.

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About a week after the meeting with Bulger, Halloran ran into Callahan at one of their watering holes and asked where things stood on Wheeler. Callahan was a little evasive and said they were still “working out the details”—as if they were pondering the fine points of a merger. Callahan changed the subject, and they bent their elbows.

A couple of weeks later Callahan called Halloran, asking him to stop by his North End apartment again. This time Callahan was waiting for him alone. He had a consolation prize for his friend, who didn’t make the hit squad. He handed Halloran a bag with $20,000 in cash—two stacks of hundred-dollar bills—and told him they had decided to take care of Wheeler without him. “Take the money,” Callahan said. “It’s best that [you] not get involved in the Wheeler deal.” Slapping him on the shoulder, Callahan said the group “should not have involved [you] to begin with.”

Halloran didn’t need much convincing to take the cash. He would not have to murder someone he didn’t know, and he had money for nothing. He viewed it as a professional courtesy from a big spender with money to burn. Halloran roared through the wad in a matter of days, spending it on furniture for his Quincy apartment, a blowout week in Fort Lauderdale, and a new car.

With Halloran on the sidelines, the Winter Hill hit team arrived in Tulsa three months later. Working off intelligence from Callahan and Rico, the team spent a week on the mundane, lethal business of checking out locations for murder, including Wheeler’s office building. But they settled on the parking lot of his country club. On a bright spring afternoon a pair of killers waited for a half-hour in a stolen 1981 tan Ford for Wheeler to finish his weekly round of golf.

Johnny Martorano, wearing a fake beard and clear, gold-rim glasses, spotted Wheeler walking briskly toward his Lincoln. He hustled to meet him on the driver’s side, carrying a .38 revolver in a paper bag. Wheeler was just settling in when Martorano pulled open the door. Wheeler leaned away while still looking directly at Martorano, who shot him once in the face. The wheelman, old Winter Hill hand Joe McDonald, raced in to pick up Martorano. They peeled away as youngsters at a nearby pool looked on and wondered what the noise was about. The hired guns drove to Oklahoma City and flew back to Florida, leaving behind a shattered family, a grieving community, and a suddenly moribund business.

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Halloran sensed he was standing at a Rubicon that ran through South Boston. His sour relationship with Bulger only complicated a deteriorating personal life. Cocaine consumption had become more important to him than cocaine sales. And he was alienated within the Winter Hill operation, hanging on to his job with Bulger’s sufferance. He had fit better with the older guys in Winter Hill—Howie Winter and Joe McDonald and Jimmy Sims—but those veterans were in jail or on the lam.

After the Wheeler murder Halloran, as a survivor of Boston’s mean streets, was acutely aware that he and Callahan had been in on a murder plot with a ruthless executioner who didn’t like him. One morning in the fall of 1981 someone took a potshot at Halloran as he emptied his trash in front of his Quincy apartment. Notice had been served.

The unraveling of Brian Halloran continued on course a few weeks later, this time by his own hand. Dealing with some fallout from the drug trade, Halloran killed dealer George Pappas at close range inside a Chinese restaurant at four in the morning after they finished their meal. Halloran fired across the table while mafioso Jackie Salemme, Frank’s younger brother, looked on. It was just like the murder in the Godfather movie, with Michael Corleone dropping the gun on the table and running out the restaurant door to a waiting car that whisked him toward Sicily, an unlikely hero in his family. But the driver in this murder just took Halloran back home to Quincy, where his problems got worse. The Chinatown execution further alienated him from his peers, who saw him spinning out of control. The murder also meant trouble with the law.

After hiding out for a month, Halloran surrendered in November 1981 and then hit the street on bail, a frazzled coke addict facing first-degree murder charges that involved a Mafia soldier. He had made himself persona non grata with the Mafia and with Bulger—the worst place to be in Boston’s underworld. Halloran had become too much trouble for just about everybody. Bulger had the opening he was looking for.

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.

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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 the tight nexus of considerations involved in his prosecution of the Angiulos partially blinded O’Sullivan. “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 US 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. Two agents accused Connolly 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.

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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. By midafternoon the pair rolled into the Topside Lounge, where Halloran, unaware that O’Sullivan had rejected him as an official informant, resumed his desperate effort to talk his way into the Witness Protection Program. At 4:30 he called the FBI and cajoled his contact agent with promises of information about another mob murder, reminding the agent of his role in two recently executed search warrants of Winter Hill gangsters. Sitting a few feet from Connolly’s desk, a noncommittal Agent Brunnick warned Halloran that it was “crazy” for him to be “bouncing” around Boston and that he should return to his Cape Cod safe house for one last weekend. An angry Halloran then cut him short, saying he was double-parked and had to go. His final words to the FBI: “Rome wasn’t built in a day you know.” Halloran had a couple consolation drinks at a table near the front window of the lounge and then walked out into a hail of bullets.

About the same time that Halloran slammed down the pay phone on the FBI, Whitey Bulger got word that Halloran was seen in a bar on Northern Avenue on the outskirts of South Boston.

Bulger went into red alert, scrambling to find Flemmi, who was out of town, and settling for Patrick Nee, a former Mullen gang member who had once been a bitter enemy. The hit team was assembled, with Nee putting on a ski mask and aide-de-camp Kevin Weeks dispatched as a spotter across the street from the restaurant, walkie-talkie in his lap.

For his part, Bulger put on a disguise of a long wig and floppy mustache and fired up his death car, a souped-up green Chevy that was stashed in a K Street garage. It was specially equipped to lay down a smoke screen for evasion and with a gear ratio that allowed it to hit 200 mph. They called it the “tow truck,” but it was a fast-moving armory with an assault rifle, a carbine, a machine gun, and several pistols.

By six o’clock everyone was in place. Halloran’s friend, Michael Donahue, pulled his blue Subaru in front of the bar.

Bulger was also in position when Halloran jumped in the passenger side. The tow truck roared beside the Subaru. Bulger yelled “Brian” as he and Nee opened fire. After a bombardment, Donahue’s car drifted slowly away from the restaurant. As Bulger made a U-turn for a second salvo, Halloran staggered free of the car and fell on the street. Still shooting from the driver’s seat, Bulger sprayed Halloran with bullets before cruising back into his Southie sanctuary. Donahue, the ultimate innocent victim, was killed instantly.

In the aftermath Weeks found Bulger “euphoric” and unable to talk about anything else for days. After he was briefed, Flemmi was disconsolate about missing out on the killings on Northern Avenue.

A Boston detective at the murder scene claimed that the dying Halloran was able to identify Charlestown gangster Jimmy Flynn as his killer, probably because Flynn looked like Bulger did in his wig and mustache disguise. Flynn also had the motive, according to police, 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 happened: Connolly warned Bulger and Bulger killed Halloran. Later, during a back-channel tip-off to Bulger and Flemmi that other FBI agents were targeting one of their bookies, 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 Bulger put Morris and Connolly on to Barrett. 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.”

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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. Not surprisingly, Connolly reported back that Callahan had no dealings with Winter Hill and that Bulger had nothing to do with the Wheeler hit. In fact, Connolly paid a chilling visit to Callahan and then alerted Bulger that Callahan was being sought as a witness in the fizzling homicide investigation. For his part, 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 Huff was foiled again.

Connolly had alerted Bulger that Callahan was facing a federal grand jury, and as much as Callahan liked hanging with wiseguys, the worry was that he wouldn’t stand up like one. The quick consensus was he had to go because he knew too much about the Wheeler murder.

Bulger summoned his most reliable designated killer, Johnny Martorano, to a hotel at LaGuardia Airport in New York to convince him to take out Callahan. Martorano, who had been a major figure in the Winter Hill gang before going on the lam to Florida, was a drinking buddy of Callahan’s, both in his Boston days and in southern Florida, where Callahan did a lot of business.

In an hour-long meeting, Bulger made a deceptive pitch. He said Halloran had told the FBI that Martorano was responsible for Wheeler, when, in fact, Halloran said it was primarily Bulger’s doing. Whitey also presented the Halloran massacre as something done to protect Martorano, and now it was time for Johnny to return the favor. Although Martorano protested that Callahan was a friend, he also understood everyone would go to jail for life if Callahan folded. He also knew that he was beholden to Bulger for monthly stipends to keep him afloat in Florida. He reluctantly agreed to do the deed.

Martorano arranged to pick up Callahan one evening after Callahan flew into Ft. Lauderdale on a business trip. It was one of Martorano’s lightning strikes, a matter-of-seconds execution. He took Callahan’s briefcase and walked him to a rented van in a far corner of the airport’s parking lot. Callahan settled into the passenger seat while Martorano put the briefcase in the back and reached under the seat for the revolver he had planted there. He immediately shot Callahan twice in the back of the head. He and an accomplice then transferred the body to the trunk of a car Callahan used in Florida and then drove it to the Miami airport garage. It was discovered the same day.

The final touch was spreading the contents of Callahan’s wallet, including his Massachusetts license, around a Cuban bar near the airport. John Connolly quickly followed up the ruse by noting in an FBI report that Callahan had alienated Cuban gangsters in Miami who were gunning for him.

John Callahan, wiseguy wannabe, 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.