Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (50 page)

For the first few months, he complained that he was strip-searched and had his cell torn apart a minimum of five times a day. The routine was maddening. “I know what Pavlov’s dog felt like,” he told a friend. He referred derisively to the guards who carried out the searches as the Just Following Orders Squad. The only upside was that, with the lights kept on twenty-four hours a day, the number and severity of his nightmares that were a legacy of his LSD testing in the 1950s seemed to abate.

He complained that the security precautions assigned to him were more onerous than those of Richard Reid, the confessed Al Qaeda “shoe bomber” who was held in Plymouth after trying to blow up a plane in 2001. He compared himself to Robert Stroud, the infamous Birdman of Alcatraz, who spent sixteen years in isolation on The Rock. With characteristic self-aggrandizement, he saw his predicament in literary terms. “I feel like Philip Nolan in ‘Man Without a Country,’” Whitey wrote. “Isolated—no human contact.” Nolan, the protagonist in Edward Everett Hale’s short story, is a US Army officer who renounces his citizenship during his trial for treason and is sentenced to spend the rest of his life at sea. Whitey saw his exile in the Plymouth jail in similarly epic terms, the punishment of a man who knew too much about his government’s dark side.

He railed against the CIA using him as a guinea pig. He railed against the FBI using him and discarding him. His upcoming trial was framed in literary terms. “Want to refute lies and try to get my name cleared,” he wrote. “That’s my Gordian Knot.” He was especially determined to prove that he did not kill the women he was charged with murdering, Debra Davis and Deborah Hussey. He called his trial The Big Show and The Big Circus. Despite occasional bouts of defiance, he was coldly realistic. “Chances are I’ll die in this cell.”

Whitey became a magnet for letter writers, the vast majority of them strangers, some of them strange. Eight women wrote asking if he was their father. He found the letters sad and wrote back, telling them that he was not. Still, he was wary of including his signature. He boasted that people were selling his autograph online for hundreds of dollars, though there is no evidence of it. Whitey seemed proud of his infamy. He claimed that an Alcatraz historian had written to him saying that the tourists who flocked to The Rock asked more about “Whitey B.” than Al Capone or other legendary inmates. Whitey’s use of his nickname is telling. Throughout his criminal career, he had angrily corrected or threatened anyone who dared call him Whitey to his face; he now embraced the moniker as part of his legend.

For someone who spent most of his life using violence or the threat of it to relieve people of their money, Whitey was genuinely miffed at the prospect of so many people trying to make money off his story. He ignored a letter from NBC’s Matt Lauer asking for an interview. He did the same when ABC came calling. He was furious that some of his former associates got paid to write nonfiction books he considered fiction. Presumably he was equally aggrieved that tipster Anna Bjornsdottir was paid two million dollars for the information that led to his and Greig’s arrest.
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Even as he faced the prospect of dying in prison, Whitey was preoccupied with his reputation, especially among those who knew him as Charlie Gasko. He wrote to friends and neighbors in Santa Monica, insisting he was not the monster he was being portrayed as, complaining about his treatment, professing his love for the woman everyone knew as Carol, wishing they were back at the Princess Eugenia, strolling the Third Street Promenade at dusk. His love for Greig was a recurring theme in all his letters. Locked up again, forty-six years after he walked out of federal prison vowing he would never go back, Whitey grew introspective, even sentimental. “Funny but the happiest years were the 16 years on the lam,” he wrote. “Quiet life, no crime, like a 16 year honeymoon. . . . Memories keep me sane.”
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Whitey’s prison correspondence revealed someone whose inner tone, as captured in his prose, had shifted, from the hard-edged staccato of the career criminal to something more like a soft romantic. He described his plight in noble, selfless terms. He spoke in a voice that suggested he had come to see himself in the same benign light that Greig had seen him in throughout their years together. He would do anything to repay the loyalty she had shown him. And as she sat in a jail in Rhode Island, he longed for her.

Whitey claimed that he was willing to plead guilty to all of the charges against him, even if it meant facing execution, in Florida, for John Callahan’s murder, or in Oklahoma, for Roger Wheeler’s, in exchange for Greig’s release. But he said that the government refused to make a deal with him: “[I] never loved anyone like I do her and offered my life (execution) if they would free her. But no they want me to suffer.”

He believed that Greig deserved praise more than prison. “She did what all the cops, prisons and courts couldn’t,” he wrote. “Got me to live crime free 16 years—for this they should give her a medal.”

Their sixteen years on the run had, he said, been transformative. Always a light drinker, he became a teetotaler. He had been able to experience the normal emotions he had shut down to survive and thrive as a criminal. Greig grew secure as Whitey’s one and only love. Hiding didn’t weigh them down; it gave them a new perspective and a desire not to waste any of their remaining days and hours together in argument. It pained him that he wasn’t allowed to write to her as they awaited trial, but he vowed to figure out a way for them to correspond, even if it meant seeking permission to get married. The return to jail, however, “brought me back to hate and shutdown—nightmares, increased hallucinations, claustrophobia. They call it security, I call it torture . . . designed to break me down.”

Even as he pined for Greig, he made peace with Teresa Stanley, who had cooperated with law enforcement while he was on the run. Stanley wrote him a conciliatory letter in jail, also noting that her son Billy had died. Billy Stanley had struggled for much of his life with drugs. Whitey told her that all was forgiven. “I did make things better for her but we fought and I had too many women in my life,” Whitey wrote to a friend. “Goes with the Fast Life.”

Another of his correspondents was Jerry Champion, an Alcatraz historian who has written books about the prison. He wrote Whitey shortly after his arrest, looking for information about his and other inmates’ experiences on The Rock. Initially, Whitey wrote back enthusiastically, but he ended their correspondence abruptly after learning from a friend that Champion worked as a prison guard in Florida. He was put off by Champion’s opining on the greatness of America and its prison system. “I’m well aware how great America is,” Whitey replied tartly. He touted his own military service, noting that he was honorably discharged and that he had always been a big supporter of the military and of veterans’ causes.
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Whitey was delighted when he got a letter out of the blue, in March 2012, from Richard Sunday, who had done time with him in Atlanta and Alcatraz. He had always been fond of Sunday. Whitey believed him when Sunday insisted that he had been railroaded on a rape charge when he was a nineteen-year-old army soldier fighting in Korea, the charge that ultimately landed him in Alcatraz. Whitey had called Sunday a few times while he was on the run but had lost contact with him when Sunday moved from Virginia to Pennsylvania. Whitey confessed to being a computer illiterate and said that he had asked a relative to do a computer search for Sunday. They’d found nothing, and Whitey had come to the conclusion that Sunday, like just about everyone else he knew from Alcatraz, was dead. Now, back in touch with his old friend, Whitey wanted to straighten some things out. “No. 1,” he wrote, “I never killed any women.” And, he insisted, he wasn’t an informant. “Sunday believe me,” he wrote. “As a kid took many a beating in the police stations trying to make me talk . . . never did . . . never gave in—never even thought of it.”

He decided he would try to be Sunday’s patron. If Whitey couldn’t capitalize on selling his story, he’d get Sunday to sell his. His old comrade had fallen on hard times, and Whitey was determined to use his infamy to help an old prison buddy. He claimed that Mark Wahlberg wanted to do a movie about him and that he could maybe persuade Wahlberg to put Sunday’s life story on the silver screen. He advised Sunday to hold on to the letters Whitey was sending him and eventually sell them. “Later I’ll write about my crime days etc. to spice up the value of the letter!”

Whitey had been a fan of Sunday’s prison poetry. He had kept a poem Sunday wrote about Billy the Kid for years, tucked inside his Bible. But he told Sunday that poetry didn’t sell; stories about crime and prison life did. In letter after letter, he sent elaborate instructions to Sunday on how to find a ghostwriter, how to use his friendship with Whitey to market his literary pitch, how to shake down TV networks for the maximum amount of money for an interview. He was relentless, offering to write the foreword if he lived long enough to do so.
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Even as federal prosecutors rejected
his offers to plead guilty in exchange for leniency for Cathy Greig, Whitey had still expected her to serve little time and to be able to leave jail and rejoin his family. “They all love her and she takes my place there,” he said. He badly misjudged the government’s attitude. Prosecutors weren’t giving an inch, and Greig threw in the towel. She agreed to plead guilty to helping Whitey evade capture. What was the point in denying it? Through a long series of court hearings, Greig appeared dour. She smiled only at her twin sister Margaret, who dutifully attended each session. She declined each opportunity to make a statement in court, letting her lawyer, Kevin Reddington, do the talking. Reddington insisted that if Greig had to do it all over again, she would. “She’s in love with the guy,” he said. “If she could be with the guy right now, she’d be with him.”

Through it all, Greig’s hard façade cracked only once. When she offered to plead guilty, a judge led her through a series of questions, asking her at one point if she had ever received psychiatric care. Greig started crying, and it took her more than a minute to compose herself. “Once,” she said. “It was after a suicide in my family.” She didn’t elaborate, but she was talking about her brother, David, who in 1984, at the age of twenty-six, put the barrel of a blue Smith & Wesson .38 special against his right temple and pulled the trigger. David Greig had been using drugs for years. Cathy Greig never cried for Whitey’s victims, but she cried for her brother, twenty-eight years after she found him in his bedroom in the family house in Southie, the gun still in his right hand. Whitey had been with her for nine years at that point and told her he’d take care of her; and, in his way, he did.

On the day Greig was sentenced, Tim Connors stood up in court to give a victim impact statement. He was a baby when his father, Eddie Connors, was gunned down by Whitey and Flemmi. Thirty-seven years had gone by. Tim Connors spoke to Greig, but she wouldn’t look at him. He reminded her of the tears she had shed when she pleaded guilty. “If I had a sister like you,” Connors said, “I would have killed myself, too.” Greig gasped, covered her mouth with her hands, and sobbed.

As cruel as Connors’s words were, Paul McGonagle’s words cut even deeper, because he was not a stranger but family; Greig had once been married to McGonagle’s uncle Bobby. As a boy, McGonagle considered Greig more than his favorite aunt. She was his friend. She took him on vacation, bought him gifts, and showered him with attention. When McGonagle was fourteen, his father, Paulie, disappeared. He spent the next twenty-seven years carrying his father’s photograph around with him, fantasizing that he’d bump into him one day and recognize him. But there was no recognizing the skeletal remains that were pulled from Paulie McGonagle’s grave on Tenean Beach in 2000. Greig had left Bobby McGonagle for Whitey Bulger, the man who shot Bobby’s brothers Paulie and Donnie.

Paul McGonagle left Southie long before he knew what happened to his father. He moved out of state, built a career, and raised a family. But he had come back to see the last hour in court of the woman who had once whispered in his ear that he was her favorite nephew; the woman who loved and harbored and took care of the man who killed his father. “Catherine Greig,” he said, “has shown herself to have a knowing and willful disregard for the law but also a callous disregard to me and my family.”

Judge Douglas Woodlock sentenced Greig to eight years—six months for each year she spent on the run with Whitey, a period the judge called “sixteen years of extended banality.” He ordered her to pay a $150,000 fine. The sentence was harsh: She got three more years than Kevin Weeks, who watched Whitey murder people and buried the bodies, and only a few years less than John Martorano, who admitting to killing twenty people. But she said nothing, smiled wanly at her sister, and left the courtroom wearing the same mask of detached stoicism she had donned for all her public appearances. Whitey was rattled by Greig’s sentence and outraged by the government’s attempt to seize the homes of Greig and her sister. Margaret’s house in Southie had been in the family for more than a century. “The government is relentless and heartless,” Whitey wrote, without a trace of irony.

Greig’s long sentence led Whitey to reevaluate his own plans. It gave him a new will to live, at least until she got out of prison. “Felt if she was free I’d hang on for couple of years and by then it’s over—need the rest. But now it’s hang in there for Catherine’s sake.”
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Greig’s sentencing also seemed to shift the tone and phrasing of Whitey’s jail correspondence. The romantic themes turned more cynical, the focus more on times and places and people lost. The wistful voice toughened again. The government, Whitey fumed, had ruined his woman, ruined his family, and, by busing Southie kids out of their schools and allowing outsiders into the projects, ruined his old neighborhood. Whitey had only seen fleeting glances of the new, glitzy Southie when he was whisked by armored SUV to the courthouse. But from the air, when a Coast Guard helicopter flew him up from Plymouth for a court appearance, the outlines of Southie didn’t look that different. The projects he grew up in looked much as he remembered. The brick building at 41 Logan Way had hardly changed since that day in 1938 when James and Jean Bulger moved their kids into the three-bedroom apartment on the third floor. “Patriotism was part of the neighborhood,” he wrote. “Sadly it’s changing. Rich people moving in, Moslems, illegals. Obama’s aunt for one.” Whitey saw nothing encouraging about the new Boston. The yuppies were bad enough. “In 16 years I’ve been gone it’s all over for the traditions etc. Progress! Not for the best.” His tone had veered markedly toward self-pity and bitterness, and he confided to one friend that he was depressed. But every once in a while, the old, defiant, vindictive Whitey would surface, suggesting no regrets. “I had a good life and I lived!” he wrote. “And Fuck Society and its Court System! I’ll laugh when I exit this world.”