Howie Carr (6 page)

In early 1955, at the age of twenty-five, Whitey fell in with an older con, a jailhouse lawyer named Carl G. Smith Jr. Smith had been serving a term at the state prison in Charlestown when he convinced the Massachusetts Supreme Judicial Court to overturn his burglary conviction on a technicality. It was his third such victory before an appeals court.

Released, Smith took up with Whitey and several other younger hoodlums, and they began organizing a bank-robbing gang. Smith and Bulger added a second-generation Cambridge hoodlum, Ronald Dermody, who would later die in the Irish Gang War. Their first score came in May 1955, when they robbed a bank in Pawtucket, Rhode Island, of $42,000. Whitey carried a .22-caliber revolver and ordered two bank employees to the floor. The three escaped in a stolen car. With $14,000 in his pocket, Whitey was finally a big shot back in South Boston. In September, he and a new girlfriend from Dorchester left Boston and journeyed to Florida, where he “registered at various motels under his true name,” according to the report the FBI would later send to his first penitentiary, in Atlanta.

In October 1955, at Smith’s behest, Whitey drove to Indiana “and there participated in the casing of the Mercantile National Bank, Hammond, Indiana,” along with Smith and a new member of the gang named Richard Barchard. The plan was to rob the bank, and they even stole a car in a nearby shopping center. But when they reached the bank, they noticed a police officer inside and immediately abandoned their plan. They returned the vehicle to the shopping center they’d stolen it from, and there they noticed that another bank “looked like a soft touch.”

A few days later, Whitey and Barchard returned to Hammond to rob the “soft touch.” With them were two women—Whitey’s Dorchester girlfriend and Barchard’s twenty-nine-year-old wife, Dorothy, who would be connected with several gangland figures in the coming years. In Hammond, they stole a ’55 Oldsmobile and headed straight to the bank.

According to the statement the FBI sent to the federal penitentiary in Atlanta in 1956, “BULGER, carrying two sidearms, and BARCHARD, unarmed, entered the victim bank. BULGER covered the employees and customers in the bank by mounting the counter. BARCHARD vaulted the counter and scooped the money from the tellers’ cages. They were unmasked during the robbery and both issued commands while in the bank. During the course of the robbery, the customers and bank employees were forced to lie on the floor.”

They wore identical sport shirts and hunting caps with ear flaps.

The take was $12,612.28. They split it, and then Whitey and his girlfriend headed to Florida for a vacation. Whitey and his female companion returned to Boston for Christmas, but he didn’t stay long. On January 4, 1956, a warrant was issued for his arrest. In a scenario very much like the one he would employ thirty-eight years later, he first fled to California, then returned a couple of weeks later to pick up his girlfriend, after which he headed to Wilmington, Delaware.

Then the couple took off across the country. They stopped in Reno, San Francisco, Salt Lake City, New Mexico, and Chicago before heading back to Boston. Among his aliases: Martin Kelley, Paul John Rose, and Leo McLaughlin.

“In a further effort to avoid apprehension,” the FBI report states, “BULGER dyed his hair black, adopted the wearing of horn-rimmed glasses, changed the style and color of his clothing, and assumed the practice of carrying a cigar in his mouth to distort his facial features.”

On March 4, 1956, Rico received a tip that Whitey had been hanging out at a nightclub in Revere. The FBI agents staked it out for a couple of nights, and finally, on the evening of March 6, they arrested Whitey as he walked out. He was unarmed and in the company of an ex-con named John DeFeo.

The next morning, at his arraignment, the prosecutor described Whitey as “a vicious person, known to carry guns, and [who] by his own admittance has an intense dislike for police and law enforcement officers.”

Bail was set at $50,000. For the Bulger family, it might as well have been $50 million.

The Bulgers managed to find a politically connected lawyer for Whitey, a former state rep who would eventually become a judge. But the case was hopeless, and on June 21, 1956, after being described by the U.S. attorney as a “habitual criminal,” Whitey was sentenced to twenty years in federal prison by U.S. District Court Judge George C. Sweeney.

“I went to court the day Jim was sentenced,” Billy wrote, leaving it at that. He had just completed his sophomore year at BC.

Whitey would not return to Boston for nine years.

Back at college, money was no longer such a pressing problem for Billy, thanks to the GI Bill. Billy’s plan, in the fall of 1955, was to finish up at BC, then go on to BC Law School, after which he would enter politics. By now he and Mary were “courting,” and often they walked to Castle Island, where they’d stand in line at Kelly’s Landing to buy a box of fried clams. Billy supplemented his income by working, not just as a lifeguard, but also as a master of ceremonies at parties held at McLaughlin & Gormley’s, a banquet hall in Dorchester.

He had returned from the army just in time to witness his hero James Michael Curley’s final campaign for mayor. In his book, Billy recalls the night of the preliminary election in 1955. He has Curley finishing second, although it was actually fourth. Billy then recounts Curley’s final concession speech, in the ballroom of the old Brunswick Hotel, quoting John Paul Jones at the end of his sixty-year political career.

“I have not yet begun to fight.”

In 1960 Representative Joe Moakley ran for the state Senate seat held by John E. Powers. Only two years earlier, Powers had become the first Democratic president of the state Senate since before the Civil War, but he was wounded. After John B. Hynes decided not to seek a fourth term as mayor in 1959, Powers had been a heavy favorite to succeed him at City Hall, but had been defeated after Boston police raided an East Boston bookie joint in a building that just happened to have a large “Powers for Mayor” sign above it. Photos had appeared on all of the front pages, and Powers lost, the victim of a classic dirty trick.

But no one had time to mourn. All that mattered in the jungle of Southie politics was that Powers was now vulnerable. Never one to stand on ceremony, Moakley sensed an opportunity, and he took it. He would not succeed in ousting Powers this time, but his decision to oppose Powers was a boon for Billy; there was now an open House seat in South Boston. Billy hadn’t expected to run so soon; he still had a year left in law school. And he was also planning to ask Mary Foley to marry him. But open House seats didn’t come along often, especially in South Boston, where service in the legislature was considered an opportunity, not a duty. But Billy’s father, growing ever more timid in his dotage, tried to talk him out of both the race and the marriage.

“You can’t support her,” Billy recounts him saying in his book. “For God’s sake don’t tell anybody about this.”

Billy and Mary were married nonetheless, at St. Margaret’s in Dorchester, where Whitey had attended parochial school twenty-five years earlier. The couple soon settled into an apartment, in Southie of course. Mary was almost immediately pregnant with Bill Jr.

Billy’s major source of income was the summer lifeguarding job, but he plunged ahead with his plans to run for Moakley’s open seat in a crowded field of sixteen candidates.

His skeptical father told Billy his opponents would use Whitey against him. For once, his father was right. In one incident, which he mentioned in his congressional testimony, one man snarled at him, “You belong in prison with your brother.”

Billy’s campaign manager was Will McDonough, his oldest friend, by now a sportswriter for the
Globe
. Another campaign worker was Roger Gill, whom Billy would reward with jobs on various state payrolls for the rest of his life. They envisioned themselves as street urchins, going up against what Billy called the F.I.F.’s—the First Irish Families of Southie.

Of necessity, Billy ran a low-budget campaign. He had a single blue suit, and his clever opponents quickly nicknamed him “One Suit” Bulger. He recalled running into Mary when she got off the subway at Andrew Square, returning from her job at the State House, and telling her he’d dipped into their rent money to buy bumper stickers. He looked chagrined, he recalled, and she smiled and offered to buy him some fried clams.

One of his most formidable opponents was Gerry O’Leary, a high school football hero who would later go to prison for an attempted $650,000 shakedown of a school bus company in 1980 while he was serving on the Boston School Committee. Another tough foe was James Collins Jr., son of a well-heeled bookmaker who would later move out of Boston and be elected treasurer of Norfolk County. Collins too would end up in prison, in 1985, for embezzling county pension funds. The Collins family’s most memorable contribution to Bulger lore would be to spread the rumor that he was actually part Polish or Lithuanian—a believable enough falsehood, given his light hair.

By most accounts, Billy and his crew simply outworked everyone else, and on primary day they prevailed. On election night, he stopped in at the parties of all his major opponents. Where they had called him “One Suit” Bulger, Billy later recalled, he told them he owed his victory to his lucky suit. When he ran into Collins’s father, he told him it was the Polish and Lithuanian votes that had put him over the top. All the while Billy kept smiling. In January he would be a state rep. Finally, a male member of the Bulger family would have a real job.

CHAPTER 2

B
ILLY
B
ULGER WAS SWORN
in as a member of the Massachusetts House of Representatives on January 5, 1961. Senator John F. Kennedy would succeed Dwight Eisenhower as president in just over two weeks.

A new era might have been about to dawn nationally, but back on Beacon Hill it was business as usual. Politics was still an overwhelmingly Irish game, so much so that an Irish name, it sometimes appeared, was all you needed in politics to succeed.

Everyone seemed to be named Hynes, or Hines, or Craven, or McDonough, or McCormack. There were Tierneys and Kearneys and Connollys galore. Both the president-elect and the state treasurer of Massachusetts were named John F. Kennedy. John E. Kerrigan would soon be joined on the Boston City Council by John J. Kerrigan.

Billy Bulger took office as one of 240 members of the House of Representatives. There were few actual offices at the State House for most of the legislators. All but about forty—the leadership and the chairmen of the more important committees—operated out of the House chambers, from their desks, which were more like open carrels in a public library. The reps had no direct phone lines; calls were taken at the bank of telephones just outside the chambers.

White flight out of the city of Boston was just beginning, and the city delegation still represented one-sixth of the House—forty of the 240 members. Twenty-three of the forty were Irish, seven were Italian, five were Yankee Republicans, and four were Jews. Of the three blacks in the delegation, two had been elected for the first time in 1960—an indication of the continuing black migration into Roxbury, which was starting to spill into North Dorchester.

The rules of life at the State House in 1961 boiled down to three points:

1. Nothing on the level.

2. Everything is a deal.

3. No deal too small.

The Boston reps lived and died by that credo. Of the forty House members from Boston who were sworn in with Billy in January 1961, at least five ended up in prison—two for income tax evasion, one for bribery, one for assaulting a federal narcotics agent, and another for larceny in connection with a state sidewalk-construction project. Another of the 1961–62 reps was eventually indicted, but acquitted, and two others, including Billy, made appearances before grand juries.

That was how Massachusetts politics operated. Edwin O’Connor, the author of
The Last Hurrah
, summed up the era in his final novel,
All in the Family
: “Corruption here had a shoddy, penny ante quality it did not have in other states.... Here everything was up for grabs and nothing was too small to steal....In our politics there seemed to be a depthless cushion of street-corner cynicism, a special kind of tainted, small-time fellowship which sent out a complex of vines and shoots so interconnected that even the sleaziest poolroom bookie managed, in some way, however obscure, to be in touch with the mayor’s office or the governor’s chair.”

Or both.

The police, by and large, were just as compromised as the politicians. As in most large urban areas, many of the cops had grown up on the same street corners with future Mob kingpins. Long before Whitey Bulger perfected the use of law enforcement as both witting and unwitting tools of organized crime, gangsters in Boston had been using them in similar ways.

Anything could be fixed—absolutely anything. Frank Salemme, Stevie Flemmi’s early partner, recalled for a congressional committee in 2003 a time when two Boston cops witnessed one of Stevie’s brothers, “Jimmy the Bear,” murder another man in a car.

“Jimmy Flemmi got out of the car and left, and they [the police] took the car and pushed it out of their division so it would be in another division and they wouldn’t have to investigate it.”

Then the cops returned to the South End, hunted down Stevie Flemmi, and demanded $2,500 in return for not turning in his brother. Stevie didn’t quibble over the amount.

“That’s the era it was, anything for money, even murder,” Salemme said. “It wasn’t considered illegal to do that kind of thing, as crazy as that may sound today.”

If, by some unimaginable bit of bad luck, you were arrested by an honest cop, and you couldn’t fix the case in the district attorney’s office, or bribe a juror, other options remained even after you were in jail.

You could buy a pardon or a commutation from the Governor’s Council, the way Raymond Patriarca, the first boss of the Mafia in New England, had done back in 1938, when a governor’s councilor even composed a letter from a nonexistent priest, attesting to Patriarca’s stellar character.