Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (12 page)

So was Whitey. But not before he took her to a department store in Dorchester to buy some new sheets. He had learned how to strip and make a bed quickly in prison, a skill he enthusiastically employed after bringing Cyr back to the Transit bartender’s apartment in Southie. Cyr found Whitey to be hypersexual. He wanted it all the time, and at the oddest times. Driving her through Southie, he would suddenly pull down an alley and pull down his pants. Another time, Cyr was working in an office building downtown, and Whitey showed up unannounced. “Follow me,” he said. She did, right into the ladies’ room, where they had sex in one of the stalls.

The sex was spontaneous, furtive, and frequent. It was also unprotected, and a few months into their relationship Cyr discovered she was pregnant. Whitey wasn’t pleased. He didn’t want a child. The Killeens had taken him aboard and he was getting some action in their bookmaking and loansharking operation. The last thing he needed was a kid. He told Cyr she should get an abortion, but she refused. They argued, and when it became clear that she wouldn’t do it, Whitey agreed to support their child. His only stipulation was that his name not appear on the birth certificate.
²⁸
A man in his business couldn’t afford known heirs; they gave his enemies a target, for extortion or kidnap or murder. Cyr listed her old boyfriend, the one she says Whitey beat up, as the father.

Cyr had a difficult labor, giving birth to a boy she named Douglas on May 22, 1967. She woke up in the hospital and found Whitey sitting by the bed. She remembers the gangster, who had little experience with babies, holding the newborn “like he was holding a time bomb.” The boy had his father’s blue eyes and blond hair, and Whitey doted on him when he was around. He visited Cyr and their son in her suburban home in Weymouth, south of Boston, at least twice a week. He helped pay for child care and showered Douglas with toys. He bought young Douglas a piano and paid for lessons. He took the boy on boating trips and family cookouts. Cyr and Douglas were welcomed at Bill Bulger’s home in Southie when Whitey brought them over on occasion.

It was an almost ordinary domestic interlude in Whitey’s life, one which coexisted in strange syncopation with his criminal doings. When Douglas was three, Cyr called Whitey in a panic. Douglas had gone to a carnival with a babysitter and had somehow wandered away. Whitey and the Killeens were, at the time, still at war with the Mullens gang, and Whitey showed up at the carnival with three other men, believing the boy had been kidnapped by his rivals. The explanation was far less dramatic. Douglas was soon found at a nearby donut shop, where a neighborhood girl had taken him without telling the babysitter.

In the fall of 1973, after Whitey had become top dog in Southie and a valued member of the Winter Hill Gang, six-year-old Douglas was rushed to Massachusetts General Hospital with a fever and nausea. The boy was diagnosed with Reye’s Syndrome, a severe, often deadly, reaction to aspirin. Whitey was one of the city’s most powerful criminals, but he could do nothing about this. He maintained a vigil at the boy’s side for three days. “When he died, Jimmy was out of his mind,” Cyr said. “Tears were streaming down Jimmy’s face.”
²⁹

The open emotion in the aftermath of Douglas’s death was quickly replaced by a new frigidity. Whitey walked into the garage in Somerville where his partners in the Winter Hill Gang congregated and told them that his son—the son they didn’t know he had—had just died. He asked them not to send flowers or go to the wake or the funeral. That’s the way he wanted it.
³⁰

Whitey paid for the boy’s funeral and accompanied Cyr to the church and burial, but if Douglas was dead, so was their relationship. Whitey swore off more children, and he swore off visiting Cyr. He didn’t want to be in the house in which Douglas had played the piano. He would meet her for sex and insist they not talk. The fun and the romance were gone. The boy’s death had changed him. “He was colder,” Cyr said.
³¹

He had always been cold,
but love had inured Cyr to it. The truth was that Whitey had never been straight with her, and even while Cyr was pregnant with his child, he’d begun a relationship with a woman named Teresa Stanley that would last almost thirty years.

Whitey had spent much of his youth trying to escape the suffocation of his family’s three-bedroom apartment on Logan Way. But even as he rebuilt his criminal career, he found in life with Stanley the sort of stable domesticity he had fled as a kid. He had been out of prison nineteen months when he walked into a bar in Southie and saw Stanley sitting on a stool. He would never have guessed that she had given birth to her fourth child just three months earlier. Stanley was a natural beauty, with sparkling blue eyes, high cheekbones, sensuous lips, and Marilyn Monroe curves. Despite being a brunette, not a blonde, she was a variation of the theme.

Aside from being stunningly attractive, Stanley was an unusual choice as a partner for an up-and-coming gangster. She had divorced her husband and was living in the Old Colony housing project, a twenty-five-year-old single mother with four kids, the oldest of whom was seven. But Whitey pursued Stanley, and she considered herself lucky. He told her that he was in the construction trade but that she’d never want for anything. He would provide the money she needed to raise her children. She would be his companion. He never called her a common-law wife, but that’s what she came to be.

From her point of view, he was a catch—a good-looking guy who always had money. What wasn’t there to like? When they walked into a bar or a restaurant, people noticed. Stanley had gone from being a single mom in the projects to something of a Southie celebrity overnight.
³²

Whitey said he didn’t want kids, but he treated Stanley’s like his own. He had firm, deeply traditional views about what constituted a family and how a family should behave. He insisted on the children sitting down for dinner as a family every night. He told the kids to tell their friends: no phone calls between 5:00 and 7:00 p.m., and if the phone rang during dinner, Whitey fumed and the kids averted their eyes. He lectured them on the importance of things he had ignored in his own early life—of doing homework, of working hard and saving money, of not hanging around with the wrong people.

But Whitey’s paternal presence, and financial support, came at a price. Stanley was by nature docile and easygoing, but Whitey expected her to be submissive. He expected her not to question him on anything. And he was frequently short and condescending.

One Christmas Eve, Stanley stood over a coffee table holding a bowl of nuts.

“I’m going to put these here,” she said, bending down.

Whitey wrinkled his brow. “Why can’t you say, ‘I’m going to place these here’?”

Stanley knew little of Whitey’s business, though she had an inkling that he made his money in gambling. On the few occasions Stanley asked the wrong question, about where Whitey had been or what he was doing, his answer was always the same: “None of your fucking business.” So she stopped asking.

“He expected perfection from everybody,” she said.

Whitey was generous to Stanley and her children. He took Stanley on vacation regularly. They traveled to Europe, to San Francisco, and very regularly to Provincetown, a resort town on the tip of Cape Cod.

Provincetown has a large and long-established gay community, and Whitey’s regular visits fueled rumors in some quarters that he was gay or bisexual. Stanley scoffed at suggestions that Whitey was anything but heterosexual. She says they went to Provincetown for the restaurants and the people watching. Despite the denials by Stanley and others who were close to Whitey, the rumors that Whitey was gay persisted. Most of them were spread by his criminal associates, for many of whom the worst insult is to be accused of being homosexual.

Whitey never took Stanley, or any woman, into his confidence, but she gave him something he would always value—a stable domestic corner in his world. It helped ground him through the brutal years of the Southie gang war and the tumult that preceded his emergence as the neighborhood’s premier criminal. She helped him, even if she didn’t know what she was helping him with.

5

Just Don’t Clip Anyone

F
or every criminal Southie produced,
it produced many more cops. At about the same time a teenaged Whitey Bulger started tailgating trucks on the Southie waterfront and along Broadway, John Connolly was in short pants, playing cops and robbers with his cousins, the Doohers, in the courtyard on O’Callaghan Way in the Old Harbor project. Connolly never deviated, in whatever game they played: he wanted to be one of the good guys.
¹
Law enforcement was a proud tradition in the neighborhood, going back to the turn of the century, when it was one of the few jobs for which being Irish was considered a winning attribute.

Connolly’s parents had immigrated to Boston from Galway, in Ireland’s rural, rocky west, settling into Old Harbor not long after the Bulgers. His father was an amiable, reserved man known around Southie as Galway John. Galway John was an usher at St. Monica’s Church and worked as a bookkeeper for fifty years at the Gillette shaving products factory, Southie’s biggest employer. Connolly’s mother, a homemaker, died relatively young, at fifty-four.

Galway John’s son wanted a badge in the worst way, but from the start he had aimed higher than becoming a Boston cop. Like Bill Bulger, young John Connolly left Southie for a more challenging school, Christopher Columbus High in the North End, the city’s Italian neighborhood and Mafia stronghold, where he walked among the bookies and sidewalk men who would later become his informants. He took Bill Bulger’s advice and enrolled at Boston College, working his way through school. After graduating, Connolly spent three years as a substitute teacher in the Boston public schools. His sister was a schoolteacher. But he had his eye on the FBI, and in true Southie fashion he made it happen through political contacts.

He was an excellent candidate for the bureau, with an engaging manner and winning blend of school smarts and street smarts. But an old sports injury to his hip prevented the twenty-eight-year-old Connolly from passing a required FBI physical. Desperate to find a way around the unexpected obstacle, he sent a letter to his father’s old friend from the neighborhood, House Speaker John McCormack, looking for help. He also called his Old Harbor friend and mentor Bill Bulger, then a South Boston state representative, asking for support.

McCormack wrote a glowing recommendation to J. Edgar Hoover. Bulger also vouched for him. But the chief of orthopedics at the US Naval Hospital in Bethesda, Maryland, who reviewed Connolly’s physical, “felt Connolly would be a poor risk for the Special Agent position” because of his hip, according to an FBI memo from Connolly’s personnel file. That same FBI memo, however, concluded that Connolly should be given another chance to apply. And it made clear that the Speaker of the House carried more clout in such matters than the navy’s chief of orthopedics. “Speaker of the House John W. McCormack subsequently advised that Connolly’s father is a close and valued friend of his and applicant’s doctor submitted a statement indicating that normal motion has now been restored in Connolly’s hip and that he is in excellent physical condition. The Director [Hoover] approved the recommendation that Connolly be afforded a complete physical examination, including orthopedic consultation, at a Government facility to determine whether he is physically qualified for the Special Agent position.”
²

This time, no surprise, Connolly passed. He was appointed as an agent in November 1968 and was assigned to the Baltimore office. In early 1970 he was transferred to San Francisco and then soon after to New York, a plum assignment for a young agent just three years out of the academy. He was closing in quickly on his goal.

Connolly’s plan always was to get back home, to make his name in the Boston office, and in 1972 Steve Flemmi played an unwitting role in making that happen. Flemmi had been out of town since 1969, after he and his then partner, Frank Salemme, bombed a car and seriously injured a lawyer who had represented a witness against the Mafia. Tipped off by his old handler, Paul Rico, that he was about to be charged with the bombing, Flemmi had gone on the lam, winding up in Montreal, where he worked as a photographer and printer. He stayed in touch with Rico, however, and with Rico’s partner, Dennis Condon, as well.

Condon had taken a run at recruiting Whitey in 1971. The war with the Mullens was in full swing, and Condon thought Whitey might be willing to trade information. In a moment of optimism, he opened, or formally listed, Whitey as an informant in May 1971, but it was clear that Whitey was not ready to be much help. “Contact with this informant on this occasion was not overly productive and it is felt that he still has some inhibitions about furnishing information,” Condon wrote on July 7, 1971. “Additional contacts will be had with him and if his productivity does not increase, consideration will be given to closing him out.”
³
Whitey was, in fact, closed out just three months after Condon opened him, and it is unclear whether Whitey even knew he was considered an informant for that brief time. Either way, he wouldn’t play ball. Condon was from Charlestown. That was enough for Whitey not to trust him.

But Flemmi did. He let Rico and Condon know Salemme was still in New York. Shortly after, in December 1972, Salemme was walking down a sidewalk in Manhattan when Connolly picked him out of the crowd and arrested him. The collar was worthy of a commendation and a coveted transfer home. It is widely believed, if never entirely proven, that Rico and Condon told Connolly where he could find Salemme. Connolly denies it, and Flemmi insists it was a Providence mobster who offered the tip. But Salemme didn’t buy it; he still doesn’t. He believes it was Flemmi who gave him up, and the chain of events makes his case a persuasive one.
⁴

If the story behind the Salemme arrest remained unclear, what happened next was not: Connolly was transferred to Boston, where he was soon given a job that would allow him to follow in the footsteps of Rico and Condon: rolling gangsters into informants. Cultivating informants was the primary job of FBI agents at the time, and Connolly was made for it. He was gregarious and charismatic, a back-slapping raconteur with a ready smile. He dressed more like a wiseguy than a cop. His suits were tailored, flashier than the button-down agents’ suits. His lapels were wide, his ties wider. Like many of the men he was trying to cajole, Connolly wore a pinky ring—again, an anomaly among FBI agents. And he liked to have his nails manicured. He also wore his thick black hair in a pompadour, leading Whitey to bestow one of the several nicknames he had for Connolly: Elvis.

Connolly carried himself with a cockiness bordering on arrogance that was common in Southie, and he was as popular in his new office as he was in his old neighborhood. Other agents, many of whom didn’t grow up in Boston, marveled at his array of friends and contacts, from big-shot politicians to the sort of guys who could get tickets to the most sought-after Red Sox, Bruins, and Celtics games. Connolly’s accent and his mannerisms, not to mention his local knowledge, opened doors and gave him credibility with people on both sides of the law. Growing up in Old Harbor made him streetwise; going to Boston College provided access to the city’s biggest politicians and businessmen. His irrepressible friendliness made him a natural gatherer of intelligence. He was good at what he did.

The Salemme pinch not only got Connolly transferred back home; it brought Flemmi back, too. Salemme was convicted of bombing the lawyer’s car and sentenced to thirty years. The witness who testified against Salemme conveniently recanted his testimony against Flemmi. The message from Paul Rico, his old FBI handler, was plain: It is safe to come home.
⁵

After the charges were dropped, the Mafia threw a party for Flemmi. It was really an excuse to recruit him. They held it at Giro’s, a restaurant in the North End. Larry Baione, the No. 2 man in the local Mafia, buttonholed Flemmi alone in a corner of the restaurant and said it was time Flemmi was made. Baione offered to be his sponsor.

Baione, spreading his arms with delight at the thought of having his own mole in the middle of a gang that was simultaneously the Mafia’s biggest ally and its most formidable competitor, suggested that Flemmi could be the Mafia’s “eyes and ears” on Winter Hill. Flemmi shook his head. He appreciated the offer, but it wasn’t for him. Later, Flemmi went up to the garage on Marshall Street in Somerville and told his friends about Baione’s offer.

They all had a good laugh.
⁶

Whitey was spending more and more time
in that garage in Somerville. Marshall Motors was a working auto body shop with service bays for ten cars, but it was really the headquarters of the Winter Hill Gang. Gamblers who owed the gang money were marched into Howie Winter’s office in the middle of the garage, where, after admiring the cheesy wood paneling, they would inevitably notice a trap door open on the floor. Howie sat at his desk and, against the backdrop of mechanics’ drills, explained the virtues of paying one’s debts. Howie’s powers of persuasion were legendary, and he never had to make good on the implied threat to throw anyone through the trap door.
⁷

Whitey, during his daily visits, would shoot the breeze with Howie Winter and his partners. Whatever money Whitey had made presiding over the rackets in Southie was dwarfed by the potential haul he could share in by working with Winter Hill. The gang’s tentacles stretched across much of the metropolitan area, and all the way north to Lowell, an industrial city thirty miles outside Boston.

Business at the garage consisted mostly of dealing with bookies and gamblers who had borrowed money and were dropping off cash. But the garage was also something of a social mecca for the crooked set. The wives and girlfriends of the assembled gangsters took turns cooking and dropping off food. One day, after the women dropped by with a batch of spaghetti and meatballs, Whitey tied one of them to a chair in Howie Winter’s office and, just for sport, repeatedly threw a knife into the wall behind her, like a circus act. “I remember saying, ‘What the hell is with this guy?’ He thought it was funny,” Winter said. “Everybody was rolling their eyes, saying, ‘What is this guy doing?’”
⁸

Between 1972 and 1975, business was good. In 1975, however, the talk inside the garage began to circle around the uneasy alliance between Winter Hill and the Mafia. Whitey along with the others sensed that things had begun to fray; the conversation turned to the likelihood of war. Like the rest of Winter Hill, Whitey wasn’t afraid of the Mafia’s guns as much as its connections: The Italian mob had many more police and politicians in its pockets, the kind of allies who could tip the balance.

On one level, Whitey knew he was insulated from any future mayhem: The South Boston territory he ruled for Winter Hill was never going to be taken over by the Mafia. There were just too many Irish and too few Italians in Southie to make that a possibility. But Whitey had grown up hearing the cautionary tale of Frank Wallace and the Gustin Gang being ambushed by the Italians in the North End. The memory of that treachery was deeply embedded in Southie’s subculture.

Winter Hill and the Mafia had long tried to make nice with each other because there was so much money to be made, and peace was better for business than war. But on occasion the sides clashed when they were going after the same money. The beef in 1975 started over vending machines. A vending company was paying the Mafia fifty thousand dollars a month to keep its machines in the bars in and around Boston. The Hill wanted the Mafia-controlled machines out of their bars in Somerville, Charlestown, Southie, Roxbury, and Dorchester so they could install their own.

Jerry Angiulo, who ran the Mafia in Boston as underboss of the Rhode Island–based Patriarca family, was livid when he found out that Howie Winter and his crew were driving the vending company out. In the Boston FBI office, the news of Angiulo’s fury stirred worry but also a sense of possibility, a chance to cultivate ties with one side or both. One of Connolly’s informants who was close to Whitey told Connolly that Winter Hill was planning to kill a group of Mafiosi. That would start a war, a war maybe worse than the one in the 1960s that killed sixty men. Connolly went to his supervisor, Jim Scanlan, and proposed taking a run at turning Whitey. Why not, Scanlan replied.
⁹

Connolly got word to Whitey through a mutual friend that he wanted to talk to him. Word came back that it couldn’t be in Southie. And it couldn’t be in public. A date and a time were set, and then the place: at the far end of Wollaston Beach in Quincy, just a few miles down the coast.

“What’s he driving?” Whitey asked. He’d find the car in the dark.

It was September 18, 1975, a Thursday night.
Whitey Bulger always listened to the car radio, and as he drove to the meeting the news was full of reports that Patty Hearst, the newspaper heiress, had just been arrested in San Francisco. She was charged with bank robbery, just like Whitey had been twenty years before.

It was almost 10:00 p.m. when John Connolly backed his car into a parking space on the far end of Wollaston Beach. The Boston skyline twinkled in the distance. The moon was nearly full, and its yellowish glow filled the car. There was only one other car nearby. When Connolly looked over he saw what appeared to be two men having a tryst in the backseat, so he moved his car further down the beach, again backing in, so he’d be able to see Whitey’s approach.
¹⁰

Like Paul Rico before him, Connolly considered himself especially adept at developing informants. It was, he believed, a science and an art. Like Rico, he killed them with kindness, earning respect by showing respect, even to wiseguys. Especially to wiseguys. One day, for example, when Connolly went to arrest a mob associate named Richie Floramo, the gangster’s kids came to the door. Connolly said he was a lawyer and needed to talk to their dad. Then he led Richie out to the car, eschewing bureau rules in not handcuffing him. Years later, when Connolly walked into Floramo’s restaurant, Floramo greeted him warmly and introduced him to his now-grown kids at the bar. Floramo had never forgotten, and greatly appreciated, that Connolly had not humiliated him in front of his children.
¹¹