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.