Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (6 page)

A few days after the New Year, authorities in Indiana issued a warrant for Whitey’s arrest. He later told prison officials that Carl Smith “squealed on us” after Smith was arrested with two men from Tennessee robbing a bank. Whitey got wind of the warrant and drove cross-country to California. But he missed Jacquie, so he drove back to Southie and picked her up at her mother’s house on Dorchester Street. They drove south, to Wilmington, Delaware, and spent the next two months on the road. They made stops in Reno, San Francisco, Salt Lake City, and Chicago. But Jacquie got homesick. She missed her six-year-old daughter and her life in Southie and begged Whitey to bring her home. Against his better judgment, Whitey turned the car around and headed east.

Back in town, he dyed his hair black, donned horn-rimmed glasses, and tried to stay inside as much as possible. When he did walk around Southie, he had a cigar in his mouth, because it distorted his facial appearance.
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But this proved useless when an informant called the FBI in Boston and said Whitey was back. The informant had spotted Whitey at a nightclub in Revere, a city north of Boston; the FBI and police pounced. His arrest was widely touted by the FBI. The special agent in charge of the Boston office, usually a desk jockey, turned up for the festivities and was prominently displayed in the photos splashed in the next day’s paper, which showed Whitey being taken from the nightclub in handcuffs. The FBI field agent who put the cuffs on him was Paul Rico, an ambitious investigator who specialized in organized crime. More specifically, Rico was known for having an unrivaled array of underworld informants and was always on the lookout for more.

Because he considered everyone he arrested a potential informant, Rico treated Whitey with respect and Whitey in return answered his questions. He copped to robbing the three banks and named his two accomplices in the Rhode Island robbery.
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He seems to have justified the betrayal on the premise that you can’t rat on a rat: Whitey claimed it was Carl Smith who had dimed them all out. But Whitey also claims he admitted his role and implicated his accomplices to save Jacquie. The FBI had threatened to charge her as being a lookout for the Indiana bank job. He later told a friend that he had offered to plead guilty if the FBI would release Jacquie.
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He also cajoled Jacquie into cooperating with the FBI, and she identified Barchard as having been with Whitey on the Indiana job and said O’Brien had been with Whitey in Melrose. “Bulger orally admitted who his accomplices were in these bank robberies,” FBI agent Herbert Briick wrote. This is the first known instance of Whitey, the prideful stand-up guy, acquiescing to the role of informer. But he was cute about it, as he would always be. In a slick move that foreshadowed their future relationship, Whitey and his FBI handlers purposely masked his role in implicating his fellow thieves. While Whitey only verbally identified his accomplices, he persuaded Jacquie to formally identify them. “As a result of her cooperation,” Briick wrote, “process was obtained for Bulger’s accomplices.” Jacquie’s cooperation won her a free pass on prosecution, and Whitey’s role in snitching on his accomplices was never made public. Being labeled an informer was not just humiliating; in Whitey’s business, it could easily get you killed.

Perhaps Whitey thought that his quickness to cooperate in the case, and his role in getting Jacquie to do so as well, would earn him a measure of leniency, such as he had enjoyed in his years as a juvenile offender. But this time the judge in the case took a much dimmer view of his character and prospects for rehabilitation, for Whitey’s local image had changed. In the year that he was robbing banks, he had simply stopped going to Logan Way. He lived out of town, often out of state, to avoid the police. By cutting himself off from his parents and siblings, Whitey appeared to the court to be a more generic sort of scoundrel, a rootless criminal. The presentencing report that Judge George Sweeney reviewed painted him as having “very little to do with his parents. It may be noted that during his formative years his father was very strict with him and on occasions beat him severely. This, however, had very little effect on him as he continued to misbehave in the community. According to his parents he comes home occasionally but, for the most part, has been living elsewhere. His family would not be affected in any way if he were given a severe jail sentence.”
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The report also indicated that Whitey’s IQ was 118, “which indicates above average intelligence. He has always been a leader and knows the difference between right and wrong. His actions have been in accord with his own choosing. The prognosis for future behavior in society is poor.”

Sweeney agreed and gave Whitey twenty years. The prosecutor had asked for twenty-five. But Whitey’s lawyer, Ted Glynn, pleaded for some leniency, noting in court that Whitey had shown some remorse and had cooperated with authorities.
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As a kid, Whitey had had no time for clergy, even the much-admired Father Leo Dwyer at St. Monica’s. But after he was locked up, he sought guidance and comfort from a priest, the Rev. Robert Drinan, a family friend whom Bill Bulger had met at Boston College. Bill Bulger had asked the Jesuit priest to help his brother.
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Whitey and Drinan struck up a correspondence, and a friendship.

Two days after he was sentenced, while awaiting his transfer to a federal lockup for processing, Whitey sat on his bunk in Charles Street Jail in Boston. It was a foreboding, damp, Victorian prison, the city’s oldest, where the rats were so big inmates said you could hear their footsteps in the dark. It had been, at various times, the holding tank for some famous lawbreakers—James Michael Curley, Sacco and Vanzetti, Malcolm X—and many of lesser note like Whitey.
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But Whitey’s mood didn’t match his grim surroundings as he wrote to Drinan, who had just been appointed dean at Boston College Law School. Drinan had visited Whitey since his arrest and had vouched for the Bulger family in presentencing reports.

For a twenty-six-year-old man who had just gotten a twenty-year prison sentence, Whitey was remarkably lacking in self-pity and seemed almost ebullient. The certainty of twenty years in prison was preferable to the unknown risks and certain disgrace of the life he’d been living. He seemed determined to make the best of it. “I thank you from the bottom of my heart for all the help you have given me,” he wrote to Drinan. Whitey pledged to put his time in prison to good use. He considered himself fortunate to be sent to a federal prison instead of a state penitentiary; the quality of life was said to be higher. “Things have turned out very well for me. The twenty year sentence pleases me. . . . I feel so much better now that I know I can look forward to getting out some day. These years will be put to good use. I’m eager to leave here and get settled down at the next place. I’m lucky to be going to a federal prison rather than a state prison. The conditions are supposed to be much better.” Whitey said he’d had a chance to say farewell to his family and his girlfriend, and that he had gotten some books to read from his brother Bill; but he wished he’d had one more chance to see Drinan. “I can’t think of anything else to say except I wish I could really let you know just how I do appreciate how things have turned out. I’m going to say goodnight and I do hope to see you again.” He signed the letter, “Your friend, Jim.”
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If the letter to Father Drinan was remarkable for its optimism and introspection, it was also notable in one other aspect: Whitey had noted on the top left corner the conditions under which it was written—in the dark. “Writing this after lights out,” Whitey said. The lights would go out early for the next nine years. The one who always walked out—out of school, out of his home, out of the safe cocoon of Old Harbor—was now a guest of the Federal Bureau of Prisons. And he described it almost as a relief. For the restless boy from Logan Way, there was nowhere to go but up.

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In 2007, the Charles Street Jail was converted into the Liberty Hotel, one of the most expensive in the city.

3

The University of Alcatraz

W
hitey Bulger was standing on Pier 4
at Fort Mason, waiting to board the
Warden Johnston
, a sixty-five-foot boat that traveled between the mainland and a small island in the middle of San Francisco Bay. He remembered the city fondly and well, though it had been a while since he’d last visited, back when he was a bank robber on the run, with money in his pockets and a girlfriend at his side. Now he was in chains and federal marshals stood next to him. It was the second week of November 1959 and the air was chilly and slightly sweet from the nearby Ghirardelli Chocolate factory. The fading chime of cable car bells echoed over the dull hum of the
Warden Johnston
’s idling diesel engine. San Francisco rose majestically behind him. The Golden Gate Bridge was off to his left, but looming most vividly was that island in the bay, his new home: Alcatraz.

They called it The Rock, the island for incorrigibles. Whitey was three thousand miles away from the jail cell in Boston where he had pledged to Father Robert Drinan, the family friend and future congressman, that he would reinvent himself in prison. But now, staring out at The Rock, Whitey Bulger felt utterly cut off from Southie, from his family, from all he knew. He still meant to keep that pledge, though in this new, intimidating place, the question was how.

Alcatraz was his second stop in the federal corrections system. He had first entered prison in Atlanta in July 1956, twenty-six years old, taut and wiry at 5 feet 9½ and 148 pounds, still radiating self-confidence. He was a common criminal, of course, but an oddly impressive one, who began his twenty-year sentence for bank robbery with a plan, to read and take seriously the education he had spurned in his youth, all the while making himself eligible for parole as soon as possible. Instead, his impulsivity and the allure of trouble had gotten the better of him, as they had throughout his young life—he had always been the boy no one could quite understand or control. His plan to conform and sail through prison in the fastest possible time had gone badly awry. As he stepped onto the
Warden Johnston,
he was headed for the toughest prison in America.

Three years earlier,
Whitey had arrived in Atlanta in the summer sun, and even with the prospect of two decades in prison ahead of him, the Beaux-Arts façade of the federal penitentiary had looked deceptively inviting. But that view was only for those on the outside. Whitey was driven to the back gate, where the new inmates were received, and reality quickly set in. He could see the sprawling, three-hundred-acre prison for what it was. Armed guards manned the looming watchtowers. Rows and rows of tiered cells, enough for more than a thousand inmates, were stacked in the middle of the main yard.

Whitey was shocked to find that he would have not one cellmate but seven. There were four bunk beds crammed in the cell. There was a toilet against the wall, one sink to wash your face in, and a smaller sink to brush your teeth. The humiliation of being forced to use the toilet in full view of seven other men was nothing, in Whitey’s mind, compared to his inability to get away from the constant, banal chatter of his cellmates. It wasn’t that he had no interest in the predictable subject matter—sex, cars, money—it was that they talked of nothing else. Many of them were short-timers, counting days and months, while Whitey was looking at years. He had goals and saw himself as a young man with prospects. All they had was their maddening, relentless, trivial talk. Whitey couldn’t read; he couldn’t think. The distraction was unnerving and then infuriating, and he began to worry that one day he’d punch someone and land in the hole, an isolation cell where there was no reading, no mail, nothing but walls.

In time, he did find some relief by taking a job in the prison’s “education department,” which meant he could spend a lot of time in the library. He lifted weights to relieve his nervous energy and to put some bulk on his frame. But there was something heavier than prison monotony weighing on Whitey. Almost as soon as he’d arrived in Atlanta, FBI agents turned up to question him about yet another crime: They said two of his bank robbery accomplices had implicated him in a murder in Indiana.
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The robbers claimed that they had dumped the victim in a lake. Investigators dragged the lake and did not find a body, but still they considered the information credible and warned Whitey and Atlanta prison authorities that a murder charge was imminent. Whitey insisted he was innocent, that he didn’t know anything about a murder—and he was telling the truth, in this case, although prison officials had no way to know that. “[Whitey] wrote an anxious letter to his brother about this charge but it was difficult to tell whether he was bragging or complaining,” prison authorities wrote. “Under any circumstances he appears deeply concerned and such a warrant in all probability will affect his adjustment here.”
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Distraught that he might be indicted for a crime that could turn his long sentence into life in prison, Whitey found his cellmates’ chatter even more unbearable. He needed to think and had nowhere to do so. His patience was gone; he was about to snap. After just three months in the prison, he checked himself into the prison’s psychiatric ward, complaining that “other men in his cell got on his nerves.”
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There was a method to his self-admitted madness; he wanted to be placed in a single cell permanently. As he sat in the ward, he wrote a two-page letter to Father Drinan in Boston, pleading for help. The priest wasn’t just a friend and a spiritual adviser, he was also a lawyer, and Whitey was looking for legal advice.
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Whitey told the priest he was feeling mixed up. He thought he was doing all the right things. He was working in the library. He was going to chapel on Sundays. “I’m no angel but as you know I’ve got a twenty year sentence and I know if I don’t help myself and put this time to good use I will have no future. I can only help myself by an education and forming good habits and sensible outlook on life,” he wrote.

He told the priest that the distraction in his cell was so bad he couldn’t read there. He was bottling up his emotions. He wondered if he had any grounds to demand a cell transfer, and asked Drinan to explain the situation to his brother Bill, who would update his family and Jacquie. Whitey’s plea never reached the priest. The letter was confiscated by prison officials, who reviewed all outgoing mail and prohibited inmates from revealing details of their incarceration. Still, Whitey finally managed to persuade staff on his own that it was best to move him. His new, solitary cell was no panacea. He was still on edge, worried about the murder case, and feeling the distance from home. No one had visited him, and while he was writing to his family regularly, the return mail was spotty. Letters from home were being withheld or delivered weeks late. A few months after Whitey wrangled himself a single cell, he got into a fight with another inmate in the morning bath line. It was his first infraction and he was briefly put in segregation and lost ten days of “good time.” The prison system rewarded model behavior by allowing inmates to shave up to ten days off their sentences each month by staying out of trouble.
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It was a considerable incentive, one that Whitey had intended to make full use of.

Bill Bulger, ever the good son to Whitey’s bad, graduated from Boston College Law School and became a state representative while his older brother was in prison. Insistent, organized, and able, Bill soon emerged as Whitey’s principal advocate and protector. He frequently called and wrote prison officials complaining about how his brother was being treated and urging them to transfer him closer to home.
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He found a powerful ally in a family friend from the neighborhood: US Congressman John W. McCormack, who rose from House Majority Leader to Speaker while Whitey was behind bars. Bill Bulger relied on McCormack’s political influence to make sure his brother did not get lost in the system, and McCormack called the director of the Bureau of Prisons in Washington to request updates on Whitey’s progress and to arrange prison visits by Whitey’s family and several friends.
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In describing his personal debt to McCormack, Bill Bulger
.
said that the congressman kept his family apprised of Whitey’s situation in prison. “I remembered his saying to my father, ‘James made a mistake and is paying for it, but he can change if they give him a chance.’”
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Bill believed his brother wanted to change. He visited Whitey twice at the Atlanta prison and wrote to the warden before each trip, urging him to waive the customary seven-day waiting period between visits so he could see Whitey two days in a row.
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“This visit to my brother can only be an annual trip for me due to the heavy expense and the time taken from work and school,” Bill Bulger wrote, noting that his brother did not get very many visitors because he was so far from home. Whitey wasn’t happy, but he and his family on the outside were gradually learning how to navigate the ins and outs of a sometimes infuriatingly unresponsive system. As Whitey eyed the calendar and calculated the good time he was earning each month, he signed up for another way to trim days off his sentence. It proved a bad bargain.

The Atlanta penitentiary’s façade
did more than mask the factory-like complex lurking behind it. It put a benign face on another unseemly facet of prison life in Whitey’s day: the use of inmates as guinea pigs in medical studies and experiments.

With a 1963 parole date his entire focus, Whitey was preoccupied with earning as much good conduct time as possible, and so he was intrigued when he learned about a way to earn added credits not long after taking a job as an attendant in the prison hospital. Dr. Carl Pfeiffer, a noted pharmacologist and researcher from Emory University, told Whitey and other inmates that he was conducting a study looking for a cure to schizophrenia. He said volunteers would be injected with a hallucinogenic drug called LSD, which at the time meant nothing to them: Few people outside the research community had ever heard of lysergic acid diethylamide, or knew of its effects, in 1957. In exchange, inmates would receive small cash deposits in their prison savings accounts and a promise that they would be credited with enough good conduct time to shave months off their sentences.
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What they were not told is that the LSD injections were part of an effort, sponsored by the Central Intelligence Agency (CIA), to develop a mind-control weapon. Project MKUltra, the agency’s secret program of research into behavior modification, mostly recruited college students and other doctors. The Atlanta prison was just one of eighty-six universities and institutions involved in the testing, which ran from 1953 to 1964.
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On August 6, 1957, Whitey signed a contract affirming that he understood “the hallucinatory effect of lysergic acid diethyl amide, LSD-25” and that “the potential benefits to humanity, and the risks to my health of participation in this study have been explained to me . . . and I hereby freely assume all such risks.”
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Six days later he reported to the psychiatric ward, a large, antiseptic room with bars and a locked steel door in the basement of the prison hospital, where he was injected with his first dose of LSD. It was a routine that would continue once a week for the next fifteen months. Whitey got three dollars for every injection, and fifty-four days off his sentence in total, but it was a devastating compact. The hallucinatory effects of the LSD would last a lifetime and Whitey would bitterly recall, years later, how he felt tricked into taking something that nearly drove him mad and would forever rob him of a good night’s sleep.
¹³

The hallucinations began within minutes of the injection. Suddenly, blood seemed to explode from the walls and drown him. The inmate sitting next to him turned into a skeleton. The bars on the windows morphed into writhing black snakes. He and the other test subjects became “raving . . . totally out of control mental and psychological animals.” Whitey felt depressed and suicidal after the sessions. He said two inmates in the project became psychotic and were shipped off to the federal prison hospital in Missouri.
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Richard Sunday, an inmate who worked in the prison hospital with Whitey and became one of his closest friends, witnessed the effect of the experimental injections and was horrified. Whitey, he said, screamed wildly and babbled incoherently. His face was contorted. “He was one crazy individual when he was on those drugs,” Sunday said.
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“He was a lunatic.”
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Sunday urged Whitey to drop out, but Whitey trusted Dr. Pfeiffer and stuck with it. For someone who had shown little respect for authority before he got to prison, Bulger was surprisingly deferential to the doctor. Years later, he would threaten to hunt down and kill Pfeiffer, but his trust was implicit when he was in prison. Sunday speculated it was a manifestation of Whitey’s sense of duty, an extension of his patriotism, that he saw the LSD project as a form of public service.
¹⁷

This uncharacteristic bow to authority may have been an outgrowth of his upbringing in South Boston, where loyalty and pride in the blue-collar, working-class neighborhood fused, for most, with an unquestioning love of country. Young men felt a duty to join the military, and Southie has had a disproportionate share of soldiers killed in action over many generations. Street corners, parks, and schools are named in their honor. Despite his own very sketchy service record, Whitey prided himself on being a veteran. It rankled when other inmates went off on anti-American rants. “People in there talked about the country like a dog,” said Sunday, a decorated US Army veteran who was sent to prison after a military court found him guilty of raping a woman when he served in Korea. “I was extremely patriotic . . . Jimmy [Bulger] was also patriotic. He did not want to hear any commie talk about the country.”
¹⁸

Plagued by persistent insomnia and nightmares after the injections, Whitey went to the infirmary, begging to be excused from work and left alone in his cell for a day while he recovered. “Shook up from LSD project,” a medical staffer wrote on Whitey’s medical chart after examining him one day.
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After fifteen months, doctors dropped him from the study because he was “persistently noisy and boisterous to a rather extreme degree.”
²⁰
It’s unclear whether they were running out of volunteers or Whitey settled down, but, still desperate to earn good conduct time, he rejoined the LSD study for six weeks the following summer. He also volunteered for a less grueling experiment, testing a vaccine for whooping cough. He was rewarded with one dollar for each vaccination, two dollars for each blood test, and three days’ additional good conduct time each month.
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Gradually and painfully, he was earning his way out.