by The Brothers Bulger: How They Terrorized;Corrupted Boston for a Quarter Century
It didn’t matter much to Billy who won the governorship. Whoever the governor was, he was going to have to play ball with Billy, and abide by his rules.
Billy controlled the Senate absolutely. Over in the House, Speaker Tommy McGee had to deal with an occasionally feisty Republican minority, as well as a band of Democratic dissidents, both liberal and conservative, who would soon oust him from the speakership. Billy, though, brooked no dissidence. Whatever he said, went.
As he settled into his middle years as Senate president, Billy grew accustomed to an ever more lavish lifestyle. He was starting to enjoy foreign junkets, at taxpayer expense. In 1982, he journeyed to China, and there was an outcry in the papers. But as the trips became more and more frequent, the negative stories became less frequent. In June 1984, he was off to Israel, and in September 1985 he journeyed to Ireland with nary a mention in the press.
For years afterward, as he traveled abroad more often, Billy worked his trips into his St. Patrick’s Day routines.
“If Dukakis goes, it’s a trade mission,” he would say. “If I go, it’s a junket.”
Kevin White had been mayor almost sixteen years. Since his near-defeat in 1975 he was a changed man. Busing had ended his national ambitions. Now he just wanted to survive, and so he used the city payroll to build a political machine of neighborhood people, from wards he felt no particular need to visit, except in election years.
The White machine soon became a magnet for criminals and grifters. At least two of his twenty-two ward bosses were excons. In the amoral atmosphere of Kevin White’s fourth term, other White operatives drifted into criminality—stealing grant money or faking disability pensions. Even the city’s low-numbered license plates began disappearing.
It was a situation made to order for an ambitious prosecutor, and his name was William Floyd Weld. After his appointment as U.S. attorney in 1981, Weld immediately focused his attentions on bringing down Kevin White and his City Hall machine.
He quickly won convictions against White’s two top operatives in Southie, then indicted the mayor’s chief fund-raiser and his budget director. At the State House, Billy watched in fascination as the feds decimated both White’s organization and his reputation. Billy began to wonder if he could parlay White’s failing fortunes into something more—the mayoralty itself. Billy had never really gotten over his disappointment at not being able to run in 1975, and now it appeared he might have another shot. After all, he could serve as both Senate president and mayor; there was no law against it, and Ray Flynn, among others, had been both a state rep and a city councilor simultaneously.
In October 1982 Billy floated the first of his trial balloons, to a reporter at the Globe. Billy, of course, was officially noncommittal, saying, “There are all the obvious reasons not to run, family and so on.”
The reporter wrote that Billy’s mention of his family was an “apparent reference to his nine children.” Whitey’s name did not appear in the story.
On May 26, 1983, a battered Kevin White announced that he would not seek a fifth term as mayor. Billy moved quickly— suddenly, he was speaking to reporters again. White’s favorability ratings had plummeted into the single digits, but he still had a citywide organization he could turn over. A week after his decision to pull out of the race, White and his wife gathered with Billy and state Treasurer Bob Crane and their wives for a lengthy, Friday night dinner at Anthony’s Pier 4. The very public message: Mayor White would support Billy.
Billy was so ecstatic that he commissioned a poll. Stories appeared that the business community was “urging” him to run.
In Billy’s own mind, at least, he seemed the perfect candidate. Was the electorate concerned about the city’s lack of revenues? That would no longer be a problem, because Billy would remain president of the Senate, assuring a steady flow of state revenues to the neighborhoods.
Billy would be the next Josiah Quincy 3rd, who had been elected mayor of Boston while serving as Senate president in 1844. He was already calling most of the shots; now he would have the title to go along with the power. Surely the voters would understand the power Billy could wield… for their benefit, of course. Through his control of the state budget, he could funnel enough money to balance the city’s books, while keeping the property tax rates low. The most powerful man at the State House would also be running City Hall. What could be better?
Then he got the poll results. Even the city’s voters, it seemed, had grown to distrust Billy. He was running in fifth place, with a mere 8 percent of the vote. The poll jolted Billy with a cold dose of political reality. At age forty-nine, he was not only unelectable statewide, which he had long known, but he probably couldn’t even win an at-large seat on the Boston City Council. Billy immediately issued a statement announcing his decision not to run for mayor. Family considerations were cited.
Billy had little impact on the 1983 mayor’s race. He endorsed no one—it would have been the kiss of death for anyone he embraced. In the end, Ray Flynn was the last white candidate standing, up against Mel King, a dashiki-clad black state rep from the South End. Flynn won easily, and Billy Bulger fumed. Southie had finally elected a mayor, and it wasn’t him.
Flynn became mayor in 1984, Billy gave him one opportunity to prove that he was a team player—for the Bulger team, naturally. Billy would forgive Ray for becoming mayor—on one condition. Zip Connolly would have to be appointed police commissioner of Boston.
Flynn refused Billy’s request. Instead he chose Francis “Mickey” Roache, another Southie guy, a career Boston cop and the brother of Buddy Roache, the hood that Whitey’s gangland pal, Billy O’Sullivan, had shot and crippled in 1971 as Whitey looked on.
Mickey Roache’s brother-in-law, Mickey Dwyer, had also been involved in the same gang war. Dwyer had somehow run afoul of the Killeens, and one night outside the old Transit Café, one of the Killeen brothers had run outside, jumped Dwyer, and bitten his nose off. A passerby had found the nose on the sidewalk, and Donnie Killeen had wrapped it in a bar napkin with a few ice cubes and then sent the nose off to the emergency room at Boston City Hospital in a taxi.
In early 1984, U.S. senator Paul Tsongas was diagnosed with cancer, and he soon announced that he would not run for a second term. Another political free-for-all was shaping up, and one of the candidates for the Senate seat was the incumbent congressman from the Merrimack Valley, James Shannon. His decision to run opened up the Fifth Congressional District seat, and Billy’s loyal Ways and Means chairman, Chester Atkins, prevailed, even though his opponent continuously assailed him as “Billy Bulger’s butler.”
What saved Chester in the end was the fact that his opponent was also a state senator, which meant that he too could be tarred with the Bulger brush. But Chester was an exception. Billy’s ties continued to doom most politicians who were close to him.
The same day that Atkins won the Democratic nomination for Congress, Billy’s majority leader, “Ditto” Dan Foley, was defeated by a reform candidate in his Worcester district. As he left the Senate chambers the next day, reporters crowded around Billy for a comment about the demise of Ditto Dan.
“He was a fine fellow,” Billy said. “He laughed at my jokes.”
Whatever Billy wanted, Billy got. When he decided he needed a three-digit license plate, he was given 979. Then it turned out that 979 had been improperly confiscated by the Registry of Motor Vehicles, and Billy had to return it. In its place, the Registry gave him an even lower tag for his white Oldsmobile—226. The new plate was issued, a spokesman for the Registry said, “to ease the pain.”
On the Massachusetts Convention Center Authority board, there was one dissident—Nick Rizzo, the appointee of the House speaker. He would later go to prison for embezzling money from the 1992 presidential campaign of Paul Tsongas, but in the early 1980s, Rizzo wasn’t yet considered dirty. He was the press’s main source of information about what was going on inside the MCCA. Rizzo just wasn’t with the program.
Mike Dukak
is didn’t want any trouble. In July 1983, when Rizzo’s term expired, he was not reappointed to the board. A year later, Tom Finnerty’s term expired. He was a team player. Dukakis reappointed him.
Life was getting better and better for Billy. As the unquestioned boss of Beacon Hill, his lecture fees rose to $3,000 a speech. He bragged about not owning a television set, and buffed his intellectual credentials by quoting John Adams and Aristotle when he came out against a bill that would have allowed reporters to shield their sources. He joined the Union Club on Park Street, where the old Southie city councilor John E. Kerrigan had once been a busboy. In Southie it began to be whispered that Billy was putting on airs, but the Union Club was a nice place to entertain his new friends like Robert Novak, the nationally syndicated columnist. And as long as Billy didn’t rock the boat for their guy Dukakis, the Globe might leave him alone.
CHAPTER 12
JAI ALAI IS NOT A SPORT EVER likely to be featured on ESPN. It’s a handball-like game, played primarily by men from the Iberian Peninsula who have long curved wicker baskets strapped to their hands.
Like dog racing, it exists, despite what its fans may say, for one reason only: gambling. Played in arenas called frontons, the sport has always been plagued by scandals. Opponents of legalized betting on professional major league sports sometimes cite jai alai as an example of what happens when gambling on human beings is legalized—sooner or later, the contests inevitably begin to be fixed. Still, despite the Winter Hill Gang’s disastrous foray into horse racing, by 1980 Whitey and Stevie couldn’t resist another shot at a gambling enterprise. But this time, in line with their emerging new philosophy, they would merely provide protection.
The company they would protect, World Jai Alai, dated back to the 1920s, and had always been owned and controlled by Bostonians. It was World Jai Alai’s founders who had actually paid for the legislative campaign to legalize the sport in Florida. By 1980, the company owned frontons in Tampa and Miami, in addition to one it had recently purchased in Hartford, Connecticut.
It was through Hartford that Whitey became involved in a string of at least four and possibly as many as six murders, two of which remain officially on the books as unsolved, too gruesome for anyone ever to have taken responsibility for.
Whitey was brought into the organization by a Boston businessman, John Callahan, an overweight, Yale-educated certified public accountant for Arthur Andersen who liked hanging around wiseguys. He had, as a Boston police detective later put it to the Miami Herald, “a bad case of gangsteritis.” For a while, he even shared an apartment in Boston with Jimmy Martorano above the Rusty Scupper, a popular 1970s-era waterfront singles bar. In the mid-1970s, the descendants of the original owners of World Jai Alai hired Callahan to run their very profitable, privately held corporation. He would only control the company for two years, but that was more than enough time to allow its thorough infiltration by organized crime.
Soon after Callahan’s hiring, H. Paul Rico retired from the FBI’s Miami office, where he had worked since 1970. Callahan, at the suggestion of his Winter Hill drinking buddies, had a job waiting for Rico, as vice president of security for World Jai Alai. Rico was the perfect man for Florida, that sunny place for shady people, as Graham Greene would say. He knew the players on both sides of the law, and he knew how to keep them happy, especially those on the FBI side. He quickly hired the wife of one of his former Miami colleagues as his secretary, and was soon squiring her FBI agent husband and at least one other Miami agent on all-expenses-paid trips to the Bahamas.
After World Jai Alai took control of the fronton in Hartford, Callahan began fretting that with the fronton’s proximity to New York, one or more of the city’s five Mafia families would try to muscle in. But Rico had just the pair to handle any problems—his old friends Whitey and Stevie.
In those days before cocaine became the focus of Whitey’s criminal empire, World Jai Alai was his steadiest, greatest source of income: $10,000 a week, skimmed from World Jai Alai’s parking revenues in Connecticut and delivered every week to South Boston. In return, he and Stevie protected the Hartford fronton from Mafia shakedowns and infiltration.
Everything at World Jai Alai was running smoothly until the late 1970s, when the descendants of the original owners decided to cash out. The State Police in Connecticut had always been wary of Callahan’s ties to organized crime back in Boston, and shortly after he brought in Whitey and Stevie, Callahan was spotted at the Playboy Club in Park Square in the company of several known mobsters. Connecticut authorities pulled his license to run a pari-mutuel, that is, a pooled betting operation. Without a license, Callahan was unable to manage the fronton, and in 1977, he was out as president.
Soon afterward, the owners of World Jai Alai sold out to a fifty-five-year-old Massachusetts native named Roger Wheeler. Wheeler, who now lived in Tulsa, Oklahoma, had heard all the stories about jai alai and organized crime, but he figured he could handle it. He’d made a fortune in electronics and cashed out some of his profits, and now he wanted a good return on his investment. What really made up his mind to buy World Jai Alai was the impeccable reputation of his vice president for security, H. Paul Rico.
If there were any problems with the Mob, Wheeler decided,
H. Paul Rico would know how to deal with them. Plus, he was hiring other newly retired FBI agents from the Miami office to work at World Jai Alai. Some of them, like Rico, had even known J. Edgar Hoover.
For $50 million, World Jai Alai looked like a steal. With annual profits of $6 million, Wheeler could quickly pay off his loans. But he should have recognized some warning signs. The First National Bank of Boston, where Callahan was well known from his days as a bank consultant, gave him good terms on the loan, except on one point. The bank insisted that Wheeler hire an associate of Callahan’s as his president.
In addition, much of Callahan’s old crew remained in place at World Jai Alai and so the skimming deal with Winter Hill remained in effect, if off the books. Wheeler suspected there was a problem, but Callahan had been a skilled enough accountant to paper it over. The new owner proceeded cautiously, auditing the books, trying to figure out just how much money was being skimmed, and how serious the theft problem was.
Peggy Westcoat was a cashier at the Miami fronton. She knew all the players in all the World Jai Alai frontons. So Wheeler approached her first. Did she know what was going on in Hartford? Callahan still had his own sources inside the company, and once he learned about Wheeler’s investigation, he made sure to tell Whitey, who began an investigation of his own. He had to find out what Westcoat had told Wheeler, and how much he now knew about the Connecticut skim.
She lived with her boyfriend in a single-family home in southwest Dade. In December 1980, two men broke into her house and hanged her boyfriend near the front door. Then the killers dragged Westcoat into the kitchen, looped a rope around her neck, and pushed her up against the sink. One man turned on the garbage disposal, and began feeding the rope into the grinder. Then they turned off the disposal, and, with the rope still wrapped tightly around her neck, they questioned her about the new management. When she’d told them everything they wanted to know, they turned the garbage disposal back on.
When the cops found the two bodies the next day, they chalked it up as another Miami drug deal gone bad.
In December 1980, Wheeler’s phone rang in Tulsa and one of his Florida managers told him the news. Peggy Westcoat had been murdered in Florida, but World Jai Alai’s most immediate problem was Connecticut. Two months later, Wheeler put the Hartford fronton on the block. There were too many mobsters, and Wheeler felt that by selling the Hartford fronton, he would break World Jai Alai’s long-standing ties with both the Mafia and Callahan’s gangster crew in Boston.
But selling Hartford was not an acceptable solution to Whitey, Stevie, H. Paul Rico, or John Callahan, who still dreamed of regaining formal control of World Jai Alai. No one could afford any serious investigations of the skimming—it would mean t
he end of the $10,000 a week for the Hill, and exposure of both Callahan’s role in setting up the skim and Rico’s acquiescence in the scheme.
There was only one way to avoid exposure. They would have to murder Wheeler.
It was at this point that Whitey made an uncharacteristic tactical error. For the Wheeler hit, Callahan wanted to use Brian Halloran, the Winter Hill hanger-on whose ham-handed attempt in 1974 to collect a loansharking debt for Jimmy Martorano had landed Johnny’s brother in prison (after an assist from Whitey and Stevie to the FBI). Halloran’s own rap sheet was dotted with similar screw-ups; once he and Jimmy had been arrested in possession of several unregistered firearms after he crashed their vehicle into a telephone pole while trying to outrace a police car.
He was, in short, a notorious fuck-up, and the idea of using him on an out-of-state contract assassination was simply unthinkable, except that Callahan made the suggestion. Callahan was not only an “earner,” he had also helped out Johnny Martorano when he went on the lam, lending him both his car and his apartment in Florida until he got on his feet. Callahan was the mule for the cash that Whitey and Stevie were sending south to Johnny.
In January 1981, a month after Peggy Westcoat’s murder, Callahan invited Halloran up to his waterfront apartment in Boston. Halloran arrived to find Whitey glaring at him.
Whitey didn’t like Halloran for any number of reasons. He was a drunk, he snorted coke, his brother was a state cop, he was a link to the old crew—he was tight with Howie Winter and Joe McDonald. Whitey called him “Ballonhead.” But his biggest problem was that he had driven Louie Litif to Triple O’s a year earlier. He was a potential witness against Whitey in a murder case.
