by The Brothers Bulger: How They Terrorized;Corrupted Boston for a Quarter Century
It was Whitey rather than Billy who first went to Catholic school, before the family moved to South Boston. Whitey attended St. Mark’s in Dorchester for the first grade, then switched over to St. Margaret’s for three years. It wasn’t until the family moved to Southie in 1938 that he entered the public schools.
According to his fifth grade transcript, in 1939–40, Whitey’s conduct marks dropped from month to month, from C to C– to D, and then, it appears, someone changed his E (“Very Poor”) in March-April into an A (“Best Work”).
Billy started first grade in public school. By the fourth grade, Billy was an above-average student, but his report card was not dotted with straight As. His only A for the year came in spelling.
Even as a youth, Whitey was always in trouble. The first notation on his police record comes in 1943, at age thirteen, for larceny. Quickly he advanced to assault and battery and then robbery, but was never packed off to reform school. In those days, if the cops “liked” you for a crime but couldn’t prove it, they might just give you a beating at the station house. The Boston cops “liked” Whitey a lot in those days.
“He was just a bad kid, always spoiling for trouble,” said one retired cop. “But there were a lot of bad kids around back then. No one ever could have predicted what happened, at least I hope not.”
There were two main youth gangs—the Mullens, named after Mullen Square, where they congregated, and the Shamrocks. Whitey was a Shamrock, or at least hung out with them. In his book, Billy paints a fanciful picture of Whitey’s youthful escapades that reads like something out of a novel, a movie, or both.
According to Billy, Whitey acquired an ocelot, a story not unlike the lion-in-the-basement tale of Jimmy Breslin’s novel about the Brooklyn mob and Crazy Joey Gallo’s crew, The Gang That Couldn’t Shoot Straight. He supposedly dated a stripper he met at the old Howard burlesque house in Scollay Square, who shocked Jean when she later wrote letters to Whitey after her return to Chicago. She signed them Tiger Lil.
Or so Billy wrote.
Billy may have been the more studious of the brothers, but he couldn’t always avoid getting involved with Whitey. Will McDonough, the late Boston Globe sportswriter who was Billy’s lifelong friend, used to tell the story of the day he and Billy were walking home from the beach. They were about thirteen. Suddenly, Whitey pulled over to the curb. He was driving a Cadillac convertible neither McDonough nor Billy had ever seen before. He was bare-chested and wearing a fedora, and he told the two younger boys to get in the car. They climbed in and Whitey took off toward Broadway.
As they drove along, Billy spotted another kid his age pedaling one of those old bicycles with an ice-cream chest attached to the handle bars. His name was O’Hara, and he was trying to make a few extra dollars for the summer.
“I never liked that kid,” Billy said, and Whitey just nodded. He slowed down the Cadillac and pulled behind O’Hara. Then he tapped the back of the bike with the front fender. O’Hara, alarmed, turned around long enough to see who was behind him, and when he saw the Bulgers, he took off as quickly as he could, toward Broadway. Whitey inched up behind him again and tapped the bike. O’Hara sped up even more, and so did Whitey.
“Jimmy,” said Billy, “I just said I didn’t like him. I didn’t say kill him.”
Whitey looked over and smiled at his younger brother as O’Hara sped through a stoplight, not even paying attention to the oncoming traffic as he tried to flee.
“We’re not going to kill him,” Whitey said. “When he gets to Broadway and barrels out into the street, the bus’ll kill him.”
Even in his youthful pranks, Whitey preferred someone else to do his dirty work for him.
Other parts of Whitey’s youth are mentioned less frequently. He was a handsome boy, blond, and as a teenager he found himself hanging around the Third Street Café, a real shabeen— the Gaelic word for a bar of low repute. It was a sort of neighborhood version of the bars that dotted Dover Street, across the bridge in the South End’s skid row district. Even in the immediate postwar era, Boston had a flourishing homosexual scene.
The size of the homosexual community in those days is suggested by the police manpower devoted not so much to the enforcement of the anti-sodomy laws, but to the shakedowns of those who broke the unenforceable three-hundred-year-old statutes. According to the book Improper Bostonians, compiled by the History Project, at the time Whitey began turning homosexual tricks in the late 1940s, one of the most lucrative police assignments in Boston was to the Rest Room Squad, which patrolled the bathrooms that were still open in many of the MTA subway stations. The homosexuals would be given a choice: Pay off or be arrested. In the bars of Bay Village, which on certain nights of the week catered to lesbians, the cops took out their shakedowns in trade. Many of the lesbians were blue bloods from Beacon Hill. The prospect of public scandal terrified them enough to accept the cops’ smirking offer of a trip out to the prowl car for a quick blow job rather than an arrest that would be picked up, if not by the dailies, then at least by the local weekly scandal sheet, the Mid-Town Journal.
According to survivors of the era, Whitey worked out of a couple of gay bars on Stuart Street, primarily a joint called Mario’s, which was also known as the Sail Aweigh. As a young male hustler, he quickly became adept at rolling his tricks— his police record indicates an arrest for “unarmed robbery” on March 18, 1947. Another of his favorite pickup spots was the Punch Bowl, which was frequently raided by the Vice Squad. According to one patron quoted in Improper Bostonians, the bartender would flash the “emergency lights” to warn everyone that the police had arrived.
“You had to stop dancing with your boyfriend,” he recalled, “since it was illegal back then. You could dance with a lesbian, or you could sit down.”
Whitey may have been hustling to raise some spending money, but he was never exclusively homosexual. On January 6, 1948, he was arrested by Boston police and charged with assault with intent to rape. The charge was later reduced to assault and battery, and Whitey eventually pleaded guilty to simple assault and paid a fine.
Whitey joined the air force at the end of 1948, but he was not cut out for military life. His records indicate he was fingerprinted on January 3, 1949, although the charges against him, if any, are not listed. A year later he was arrested for being AWOL. In June 1951, he was arrested on suspicion of rape, a charge that was later reduced to assault.
His records also indicate a serious problem with discipline. By June 1949, his commanding officer at Smoky Hill Air Force Base in Salina, Kansas, was trying to get Whitey thrown out of the air force on the grounds of “fraudulent enlistment,” since he had not mentioned his earlier robbery and rape arrests in Boston. But the base’s personnel officer wrote a memo to the CO, noting that there were no grounds for a discharge, since the felony charges against Whitey had been dropped.
Whitey’s disciplinary problems persisted even after he was transferred to Great Falls, Montana. A few transcripts of his disciplinary hearings have survived, and one details how, out on the parade ground, his CO told him he didn’t deserve to be a corporal.
“Well, then bust me if I don’t deserve it,” Whitey retorted. On June 24, 1952, with his term of enlistment about to expire, another disciplinary hearing, just one step short of a court-martial, was held in the matter of James J. Bulger Jr. The surviving records are sketchy, but it seems that Whitey asked for it himself, apparently because of the threat of a less-than-honorable discharge that was hanging over his head. He must have been somewhat concerned, because he told the hearing panel that if he wasn’t treated fairly, he would write his congressman. This was the first recorded instance of John McCormack’s name being dropped by a member of the Bulger family or gang.
“You know,” the captain told Whitey, “you could get a dishonorable discharge, and if that happens, you’ll never get a good job on the outside.”
According to his records, Whitey had a prophetic, classic response: “I could go back to the work
I used to do, no matter what kind of discharge I get.”
On August 16, 1952, Whitey received an honorable discharge from the United States Air Force.
Back in Boston, Whitey did indeed go back to the work he used to do. He was soon again turning occasional tricks in Bay Village, and that was where he met a twenty-six-year-old FBI agent named H. Paul Rico. Rico, a Belmont native and Boston College graduate, had joined the bureau in 1951, and could justify his sojourns to the Bay Village gay clubs as reaching out to new “sources.” But Whitey was now less interested in rolling gays than he was in the big money, and he was soon an apprentice wiseguy, a hoodlum wannabe. After Whitey’s conviction on bank robbery charges in February 1956, H. Paul Rico wrote in his pre-sentencing report to the judge that the Boston office of the FBI had long followed Bulger “because of his suspected implication in tailgate thefts. We knew of his extremely dangerous character, his remarkable agility, his reckless daring in driving vehicles, and his unstable, vicious characteristics.”
Or, as Billy put it in his book, “He had an abundance of good humor and a wildly creative talent for impish mischief.”
In 1948, at age fourteen, Billy worried that his life already seemed to be slipping away from him. He had finished the ninth grade at South Boston High, and he could already see where that led—down to the docks for the morning shape-up, or, if you were lucky, or connected, to the electric company— “the Edison.” And after work, to the corner tavern for a wee small taste of the creature—Green River whiskey washed down with a Pickwick Ale chaser—waiting for the Payoff Edition of the Record to hit the streets so you could see if you hit the “nigger-pool” lottery number. Or you could stay at Southie High and get into the sheet metal training program. Or play a varsity sport, go into the army after graduation, then come back home and take the civil service exam.
Billy wanted something more. He looked up to his Logan Way neighbor, Joe Moakley, back from the war and already at BC. Joe Moakley was going places, and Billy Bulger wanted to go places too.
But he needed to get into a good high school, one that would provide him a way out. There were only two choices: Boston Latin, the public exam school or Boston College High. Latin was tough for a Southie kid, especially one from public school and the projects. Everything came down to your score on the exam.
That left BC High. Billy put on his Sunday suit—his only suit—and walked straight to the school, unannounced. In the front lobby sat the school registrar, Charles Doherty.
“[I] explained that I wanted to go to BC High,” Billy recalled, “but that my family couldn’t afford it and I wasn’t qualified.”
He wasn’t kidding about his lack of academic credentials, so he offered to repeat the ninth grade, and pay the tuition himself. Doherty decided to take a chance on Billy, and that fall he entered as a ninth-grader. He had financial help from his older sister, Jean, who was working and engaged to be married. Plus, he still made money from his various “odd jobs,” as he put it. He occasionally worked for the Karps at the local grocery store, and in the winter the “snow button” was available from Knocko McCormack, the congressman’s brother and the biggest bookie in South Boston. If you got a “button” after a snowstorm, the city would give you a day’s pay for shoveling out the streets. The really big money was down on the docks. When Billy got lucky, he could sometimes make $3.50 an hour. In the summer, he had another public sector job, as a lifeguard at the L Street Bathhouse.
In his later high school years, he also began dating, if a bit tentatively. Jimmy Condon, the state rep whom Billy would someday join in the House, had somehow secured hundreds of passes for a day trip to Provincetown on the SS Steel Pier, and was passing them out to his constituents, even if they weren’t quite yet of voting age. On the dance floor that day Billy would meet his future wife, Mary Foley, who lived on Pacific Street. Once the ship docked, they walked the streets of the old fishing community together, chuckling at the eccentric locals. Billy recalled having 70 cents in his pocket, with which he bought fried clams.
The next spring, he took her to his BC High School senior prom. The next year, with Billy a freshman at Boston College, she invited him to her prom at Gate of Heaven High School. But by then, Billy had come to the conclusion that he couldn’t afford BC. The Jesuit fathers had waived the hefty $400 tuition for his freshman year, but now that he was finishing up his first year at the Heights, there was, as usual, no money in the till. Jean was now a brokenhearted widow—her young husband had been killed in the Korean War. With few alternatives open to him, Billy took what was then the common way out: He enlisted in the U.S. Army. There would be no OCS—Officer Candidate School—for Billy. He just wanted to do his two years, qualify for the GI Bill, and return to his old life—Southie, BC, and Mary. It was an uneventful twenty-four months, basic training at Fort Dix and then a routine assignment in the Cold War army at Fort Bliss, Texas.
Billy was discharged in August 1955, three months after Whitey had begun his new career—robbing banks.
Billy would later blame Whitey’s criminal career on falling in with “an older group.” But Whitey had been looking to hook up with a gang, because his solo life of crime was going nowhere. Almost immediately after his discharge from the air force in 1952, he’d been arrested in the Back Bay on charges of attempting to steal a beer truck—the “tailgating” referred to in the FBI memo of 1956.
In those days, much of Southie’s crime involved pilferage from trucks. An aspiring thief would either steal something off the back of a truck, or, more profitably, hijack an entire load. The hijacks were almost always inside jobs—a Teamster would be paid to turn over his load of, say, Gillette razors, to someone else from the neighborhood. Violence was rare, and the only ones who lost money in the flourishing trade were the insurance companies, and the honest policyholders who subsidized this informal redistribution of wealth with their higher premiums.
The problem for Whitey was, a few of his fellow tailgaters got set up. They might mention something about a future score to Whitey, just in passing, and sure enough, when they showed up to grab the truck, the FBI or the local cops would be there waiting. H. Paul Rico’s personnel file soon included commendations from the director, J. Edgar Hoover. At the time, no one suspected Whitey—it was inconceivable that one of Southie’s own would become a rat. Squealing might be grudgingly tolerated in some neighborhoods, but not in Southie.
But the fact was, whoever Whitey took up with usually wasn’t around very long. Whitey Bulger, his associates came to believe, was a jinx, and the tailgate jobs soon dried up.
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 the
ir 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.