Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (25 page)

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 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.

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 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.