Black Mass

by Dick Lehr

  No question, he’d taken a gift too far.

  Between himself and Connolly, Bulger and Flemmi now had two agents cold. Morris tried to warn his successor, Jim Ring, about Bulger. Morris, of course, did not mention the money. He talked to Ring in FBISPEAK, suggesting to the new supervisor that perhaps Bulger and Flemmi had “outlived their usefulness” and should be closed down as FBI informants. It was Morris’s lame wish that Ring would somehow clean up his mess. Ring later said he had no memory of Morris ever advising him to close Bulger. In the office the two agents were regarded more as rivals than as friends. Ring was eager to make his own mark, not just serve as custodian to the picked-over remains of the Angiulo case.

  Connolly immediately brought Ring around to meet Bulger and Flemmi—the start of a new chapter in glad-handing. Connolly made the initial introductions at his own apartment, and the two gangsters found that Ring wasn’t warm and soft like Morris. “I felt comfortable with John Morris, but Jim Ring was a different type of a person,” Flemmi said. “He seemed to be more focused in on details and didn’t seem to be the type of guy that wanted to maybe socialize.”

  Soon enough, though, Ring joined the others at the dinner table, including a memorable night spent at the house of Flemmi’s mother. Billy Bulger, the senate president, walked into the Flemmi kitchen from his own home across the way. The startled FBI supervisor did a double take as Billy walked right in and gave Whitey some family photographs to look at. (Billy later denied this ever happened, but Ring testified about the cameo appearance under oath.)

  But no other supervisor or fellow agent could ever replace what the group had had in John Morris. Maybe he wasn’t Connolly’s boss anymore, or in charge of the Organized Crime Squad, but Connolly and Bulger and Flemmi were going to stick close by. They had Morris in their grip, and he’d come cheap—a plane ticket for an illicit tryst. Morris soon sensed as much. He knew the moment Debbie Noseworthy buckled herself in for the flight out of Logan that it was over. He was finished, and it would only get worse as the 1980s continued. He’d try to rationalize as best he could, try to imitate Connolly—fluff everything up in earnest talk about the special deal and the special task they’d all undertaken to defeat the Mafia. But the protection they were providing Bulger and Flemmi was no longer just about gathering underworld intelligence, which was always good to get but never as vital and indispensable as the agents had portrayed it. The protection was now about FBI corruption.

  Morris had been unable to hold his own, through the Colonnade and the dinners and the gifts, through the leaks about the state police’s attempted bugging and now the cold cash. He knew full well they’d all moved far beyond crafting distortions and lies for the FBI’s files, beyond the padding of the Bulger files so that their bosses thought only good thoughts about Bulger, beyond the stretching of the rules to their outermost limits.

  They’d fallen completely off the game board during the eighteen months from late 1980 to mid-I982—now criminals all, FBI agents and two gangsters looking to deflect trouble of any kind, including charges of murder.

  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 afterwards 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.

  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 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 co-conspirators 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 26-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 break-up 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.

  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 multi-millionaire 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.

  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 chauffered 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.

  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 where 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 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 put together by the First National Bank of Boston.

  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, for just two years before he had been discharged by the World Jai Alai board of directors 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.

  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. On a bright spring afternoon Wheeler finished his weekly round of golf at an exclusive Tulsa country club and strolled from the locker room to the parking lot. Two men sat there waiting in a rented 1981 Pontiac with stolen license plates. They watched the dapper executive get into his Cadillac. Then one of the men, wearing sunglasses and a fake beard, walked briskly toward the car. He had one hand inside a brown paper bag and the determined look of a military commando on his face. As he approached the car door, the businessman looked straight at him. Johnny Martorano put the bag to the window and shot Wheeler once between the eyes with a long-barrel .38. He then walked just as briskly back to the tan sedan. The Pontiac peeled away as youngsters at a nearby swimming pool looked on and wondered what the noise was all about.

  HALLORAN sensed he was standing at a Rubicon that ran through South Boston. His sour relationship with Bulger only complica
ted 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.