Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (26 page)

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Jack Weeks was blamed, fairly or unfairly, for the idea of having Dukakis take a drive in an army tank in front of the campaign press corps. Meant to boost Dukakis’s reputation among military backers, the resulting image of the presidential candidate wearing a jumpsuit and too-large helmet backfired and was used by Republicans in commercials to demean Dukakis.

10

Overreach

T
he pitch came in the spring of 1981
from John Callahan, a sly and successful executive who, like his gangster friends, was always on the lookout for a score. Callahan asked Whitey and Stevie Flemmi to kill a businessman who was getting in his way—a legitimate guy, as the wiseguys say. It was something they had never done. Their victims had always been tied somehow to the underworld. But this was a reach. An overreach, it would turn out. But Whitey and Flemmi listened because what Callahan was dangling sounded so lucrative, so easy.

Callahan was an accountant who preferred the company of assassins. He rubbed shoulders with the gangsters he met at Chandler’s, the South End nightclub controlled by the Winter Hill Gang. He was generous with rounds; the wiseguys liked that. They also liked the fact that, despite his own legitimate job, Callahan was a rogue, willing to engage in various moneymaking and money-laundering schemes with criminals.

Callahan grew up in Medford, a blue-collar city where upwardly mobile crooks from neighboring Somerville liked to install their families. His father ran a wholesale produce company in Charlestown, a neighborhood where gangsters were almost as common as longshoremen. Callahan, with his thick build and hearty laugh, knew the life and was attracted to it. More studious than most of his peers, he joined the air force right out of high school, determined to have the military pay for his college education. The air force sent him to Yale to learn Chinese. He left the service after one tour and studied accounting at Bentley College while working for his father in Charlestown. In time he landed a job with the accounting firm Ernst & Ernst. He became a CPA and joined a bigger firm with a national profile, Arthur Andersen. A gifted schmoozer, Callahan made partner at Arthur Andersen in 1970. But it didn’t last. He liked the nightlife too much to be much good at early-morning client meetings. He often showed up hungover and unkempt, if he showed up at all, and in 1972, he left the firm to set up his own consulting business. His contacts in the banking and finance worlds rivaled his contacts in the underworld, and he would use both.

In 1974, he was hired by World Jai Alai, a Miami-based company founded in the 1930s and one of the first to turn the Basque sport of jai alai—in which a curved basket is used to catch and hurl a ball at startling velocity—into a game that could be wagered on. Betting on the sport was legal only in a few states, including Florida and Connecticut, and World Jai Alai was looking to expand.
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To do so, it hired Callahan to help the company find a new president. After reviewing the firm’s robust cash flow, the opportunistic Callahan recommended himself. The board of directors hired him on the slimmest of majority votes. Callahan’s backers pointed to his accounting skills and the banking contacts he had who could help the company get needed financing. His detractors said he knew nothing about gaming. Both sides were wrong. His contacts were less in banking than in crime, and he knew more about the gambling business than they could have imagined.

The board might have voted the other way had it known that, at the same time that they were considering hiring him, Callahan was in Boston, drinking with a Winter Hill Gang leg breaker named Brian Halloran. In the course of the evening, Halloran got into a fight with an off-duty police officer. The cop was badly beaten and Halloran wound up in jail, even after Callahan testified on his behalf. Without knowing it, World Jai Alai had hired a magnet for trouble.

Callahan’s decisions in his new job came under scrutiny almost immediately. The Boston man he hired to run the jai alai arena’s food and beverage concessions had no previous experience in the field and was known mainly as a boxer and boxing manager. The man was barely on the job when, in a fit of frustration, he kicked the freezer door in the stadium’s kitchen off its hinges.
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Callahan redeemed himself by bringing in as head of security a recently retired FBI agent who specialized in organized crime: Paul Rico. Rico seemed like a savvy hire. He had come to Callahan with the highest recommendations—from criminals. Rico, during his Boston years, had facilitated the rise of the Winter Hill Gang by helping it eliminate its rivals in Charlestown. Much like his successor in the Boston office, John Connolly, he was an agent who had grown fascinated by the underworld and then been swallowed by it. The board of directors, however, saw him only as a veteran FBI agent who would win them brownie points with jai alai’s overseers in law enforcement.

But Callahan’s taste in after-work companions, his yen for the reckless, riotous, ever-scheming side of underworld society, would eventually get him fired from World Jai Alai. In 1976, as the company was seeking to expand its operation, opening an arena in Connecticut, the board of directors asked Callahan to resign because police had complained about his open association with gangland figures. Notable among those associations were the Martorano brothers, Jimmy and Johnny, and Howie Winter, head of the Winter Hill Gang. Callahan couldn’t exactly plead innocent. On March 1, 1976, he’d spent the afternoon in a meeting with Connecticut investigators who were vetting World Jai Alai, and when the conversation drifted to the sort of people he socialized with after work he’d abruptly left, telling Connecticut State Police he had to fly to Miami. They didn’t believe him and followed behind as he drove from Hartford to Boston and then went drinking with Jimmy Martorano at the Playboy Club. Boston police later gave Connecticut State Police a series of surveillance photos showing Callahan to be a regular at Chandler’s, the Winter Hill Gang’s bar of choice.

Callahan had been exposed. He told the board he’d depart willingly if they agreed to let his friend Richard Donovan succeed him and also let Rico stay in place. The board had no idea why this was so important to him, didn’t know that Callahan and Rico had been skimming money from the company, up to a million dollars a year, mostly cash from the food and parking concessions and bets that weren’t being reported. Within two months Callahan was back with a surprising proposition—to buy the company himself for thirty-five million dollars. The board declined the offer. Next, in what should have been a tip-off, Rico proposed that Jack Cooper, a Miami Beach associate of the gangster Meyer Lansky, buy the company. Again, the board, though open to the notion of selling, demurred.
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Callahan then had what he considered an inspired idea: If an established businessman, a white knight, bought the company, the board would be pacified, law enforcement attention would be diverted, and he could still quietly skim off his share. Callahan used his business contacts in Boston to recruit Roger Wheeler, an Oklahoma entrepreneur who had made his fortune with a computer company called Telex Corp. and was in the market for investment opportunities. Wheeler was unlikely company for gamblers, and even less likely to associate with mobsters. Born in Boston, he grew up in Reading, a suburb north of the city. He attended MIT, served in the navy, then went to Notre Dame and Rice University, where he graduated with a degree in electrical engineering in 1946. He worked in the oil industry before founding companies of his own, making chemicals and metals. In 1965, he took over the then failing Telex Corporation in Tulsa and turned it into a moneymaker. Wheeler did very well but wanted more; he wanted to get rich enough to fulfill a dream and buy a home on Nantucket, the pricey, exclusive island off the coast of Massachusetts. He’d looked at the obscene profit margins of the legalized gaming industry and wanted in.
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A devout Presbyterian, Wheeler said that he opposed gambling personally but that, as long as it was legal, it was better if it were run by responsible businessmen—people like him.
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Wheeler’s subsequent failed attempts to buy racetracks, a slot machine business, and even a Las Vegas casino signaled his interest, which led to an approach by Callahan’s business contact at the First National Bank of Boston, David McKown. A loan officer with the bank, McKown had done business and was friendly with Wheeler, and told him that the jai alai company could be had for fifty million dollars. In 1977, the last year World Jai Alai was a publicly owned company, it reported net profits of five million dollars on revenues of thirty-one million dollars.
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The margins were irresistible. Wheeler said he could put up seventeen million. McKown said the bank would front the remaining thirty-three million on favorable terms. Deal.

 One of Wheeler’s first moves as owner was to send his sons to Miami to audit the company’s finances. That made Callahan extremely nervous, and well it should have. A million-dollar-a-year skim would be hard to miss. He had to find a way to pry the business away from Wheeler before Wheeler found him out, and he had an idea who could help. He called his old drinking buddy from Chandler’s, Johnny Martorano. When Martorano went on the run from the horse race–fixing indictment in 1979, it was Callahan who helped set him up with an apartment and a car in Florida. When Martorano needed cash, Callahan ferried it down to him from Boston. Now Callahan was looking for a favor. He was going to make a move on World Jai Alai, but before he did he wanted to secure Winter Hill’s muscle to protect his investment. “He was trying to buy the [business] for a lot of money,” Martorano said. “He said if the deal goes through, we’ll give you $10,000 a week, cash, through the company, parking lot, vending, whatever.”
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Once Callahan was at the helm, Winter Hill would make sure nobody, especially other criminals, bothered him. It seemed like easy money; it
was
easy money—as much in a week as Winter Hill collected in tribute from a dozen bookies in a month. Martorano ran it by the only two Winter Hill partners who still mattered—Whitey and Flemmi—and they agreed it was a no-brainer. They probably wouldn’t have to lift a finger for ten grand a week. There was only one problem. Roger Wheeler. “Callahan offered $60, $80, $100 million and the guy refused it,” Martorano said. “Roger Wheeler refused to sell.” Callahan told Martorano that Wheeler would have to go. He asked Martorano to kill him. Martorano’s first instinct was always to help a friend, and Callahan was a friend, but then he paused. Whitey and Flemmi had to approve any hit, and they were wary—not about the deal but about killing the likes of Wheeler. But Callahan was a confident man, or maybe a desperate one: He said he’d talk to Whitey and Flemmi himself.
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They met on a warm spring night at the Black Rose, an Irish pub next to Faneuil Hall Marketplace, a collection of restaurants and shops on Boston’s tourist trail. Like Whitey, Callahan styled himself an Irishman. Like Whitey, he gave money to the Irish Republican Army regularly. There was always loud live music at the Black Rose, and this night was no different. Above the din of Irish rebel songs, Callahan leaned into Whitey and Flemmi. “Listen,” Callahan told them, “Wheeler is being unreasonable.” He explained that he and Rico had decided that the only way to get the company back was to eliminate him. He was sure that Wheeler’s wife would want to sell if her husband was dead. And he said that Johnny Martorano was willing to do the hit, but only if Whitey and Flemmi were on board.
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The gangsters said they’d think about it, but as they left the raucous bar, Whitey told Flemmi he had serious reservations. For one thing, Callahan drank too much and Whitey never liked that in his partners. And as much as he liked to hang around gangsters, and as fluently as he talked the game, Callahan was a civilian, a member of no gang. Now, suddenly, he’s looking to arrange a murder?

Flemmi called Rico, his old FBI handler.

“Are you with this?” Flemmi asked.

“Yeah, I want it to happen,” Rico replied. “We want you to be part of this.”
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The hit was to take place in Tulsa, where Wheeler lived and would be most vulnerable; Rico had begun working on Wheeler’s routine, watching his patterns as he came and went from work and home, looking to find the best place and time to shoot him. But Whitey still didn’t like it. “He’s a legitimate guy,” Whitey said, pacing back and forth in Broadway Furniture, the appliance store in Southie they were using as a meeting spot. Whitey had killed a lot of people, but all of them had been criminal competitors, and Boston guys. He had survived this long in a hazardous trade by being smarter and more careful than most. This was something new and unsettling, though the money was undeniably enticing.

For days, Whitey and Flemmi went back and forth, as in a tennis, or maybe a jai-alai, match. “The guy’s a zillionaire,” Whitey said. “His family is politically connected. We’ll never survive it.”
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“This is easy, steady money,” Flemmi replied.
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Besides, their old friend Paul Rico was their insurance policy. Rico, with his FBI connections, will deflect the heat, Flemmi said. He could make anything go away. “Johnny’s gonna do this whether we’re involved or not,” Flemmi said. “He’s our partner. We’ve got to be part of this.”
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Whitey could be obstinate, but he also was susceptible to the peer pressure of criminal partnerships. When he asked his partners to do a murder, he didn’t expect a debate. He expected them to follow him unquestioningly. In the end, Flemmi wore Whitey down. He was probably the only one who could.
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But even after Flemmi had won him over, Whitey second-guessed himself. “We’re all gonna go to jail,” he told Flemmi. “This will never go away. Never.”
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It was never a good idea
to do a hit alone, especially in unfamiliar territory. Even a legendary killer like Martorano needed help, and Rico asked the old Winter Hill hit man Joe McDonald to be the accomplice. McDonald was already on the run but agreed to do it, saying he owed Rico a favor from years ago.
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Martorano and McDonald flew out to Oklahoma City and rented a car. They drove a hundred miles east toward Tulsa, checking into a series of cheap motels, the last being the Trade Winds West. Martorano liked the tiki bar there.