Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (7 page)

When he first went to prison, Whitey made good on his vow to use this time to better himself. He took typing classes and completed correspondence courses in bookkeeping, salesmanship, and business law. He began reading in a serious way and discovered an interest in historical novels about war and politics, and in autobiographies, westerns, and poetry. He subscribed to
America
, a Jesuit magazine recommended to him by Father Drinan, whose writings appeared regularly in its pages. And he was a steady letter writer, allowed, under prison rules, to correspond with ten reputable people who had passed a background check. Initially, his list included his parents, brothers, sisters, Jacquie McAuliffe, Drinan, and another priest. When his girlfriend stopped writing, he replaced her on his list with another priest, and thus the boy who couldn’t be bothered to walk the few minutes from Logan Way to St. Monica’s Church in Southie was now corresponding in prison with three priests—and going to Mass regularly. He may have found a new spirituality, or perhaps he’d simply figured out that one way to impress a parole board is to find religion behind the walls—and to show that you had reputable allies on the outside.

Whatever his motives, his image in the prison began to shift. “This man is devoted to his mother,” staff wrote on his annual review, noting that he corresponded regularly with her.
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He earned a “meritorious award” for helping physical therapy patients in the infirmary, where he demonstrated “cooperative work habits and a cheerful personality.” But for all his conscientious reputation building, Whitey still found it hard saying no to the temptation of trouble. A year after that glowing annual review, prison staff discovered he had slipped a hacksaw blade to four inmates who used it to saw their way out of the hospital. The men were captured on the roof over the prison’s dining room and an inmate informant told authorities of Whitey’s involvement.
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That Whitey would risk his institutional record for a prison escape he wasn’t even going to take part in seemed especially reckless, and prison authorities now viewed him as an escape risk, too. “Almost every time information is received about some escape plot, Bulger’s name heads the list,” Associate Warden W. H. York wrote, recommending to his boss that Whitey be transferred to Alcatraz, the nation’s first super maximum security prison.

Bill Bulger, far away and busy
with his own burgeoning career, had access to few of the day-to-day specifics of Whitey’s prison life, but it was nevertheless plain to him that things weren’t going well. He wrote to McCormack, then House Majority Leader, complaining that Whitey was in solitary confinement, cut off from communication with his family.
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McCormack personally contacted Bureau of Prisons director James Bennett, urging him to investigate the complaints, and his intervention worked: Whitey was returned to the general population, and Bennett rejected the warden’s transfer request, suggesting that the recent move to Alcatraz of two other inmates involved in the escape might work as a sufficient warning to Whitey and persuade him to behave.
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Five months later, prison authorities uncovered an escape plot planned by Whitey and several other inmates, including Tom Devaney, an enforcer for notorious Irish American mobster Mickey Spillane in Hell’s Kitchen, New York City,
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and plans to ship Whitey to Alcatraz were revived. Once again, Bill Bulger rushed to his defense, writing to the warden: “Despite the supposed tangible evidence to the contrary, I am convinced that my brother has been doing all possible to make himself eligible for parole.”
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Bill told the warden he would travel to Atlanta in the next few days and hoped for a personal meeting not just with Whitey but with the warden. Bill believed he could explain Whitey’s demeanor and his plans. “Few things are as important to me as his eventual return to a decent life,” Bill wrote.

The warden sent a reassuring letter back: “Your brother has been identified with some rather serious irregularities during the past few months here, but I am pleased to inform you that he has now emerged to full program participation and is seemingly again participating enthusiastically thereon.”
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He added, “Your writing him letters of a cheerful type and visiting him as frequently as you can reasonably do so will, no doubt, contribute to his progress.”

Bill Bulger’s next letter to Whitey did not pass the cheerfulness test and was sent back to him undelivered with a note from the warden: “Your letter to your brother James is being returned to you since the major portion of the letter concerns institutional affairs and happenings and is not a social letter in the true sense.” A few days later, after receiving a letter from his brother indicating he was still in isolation, Bill Bulger accused the staff of mistreating Whitey and deliberately delaying his letters home so he couldn’t get messages to his family. The angry back-and-forth escalated when the warden refused to deliver still another letter and accused Bill of deliberately backdating it to make it seem like the gaps in communication with Whitey were longer in fact than they were.
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The accusation infuriated Bill Bulger, who prided himself on his moral upbringing and sense of propriety. Nothing made him so hot as to have his honor challenged. He fired back an indignant four-page, handwritten note, defending his integrity and proclaiming, “I don’t lie.”
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A second-year law student at the time, Bill Bulger asked the warden to send any future letters to him at Boston College Law School in Newton, an upscale suburb west of Boston, an attempt, perhaps, to underscore that he was someone to be reckoned with.
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But the warden was done writing about Whitey. In a letter supporting his recommendation to transfer Whitey to Alcatraz, the warden wrote that he was now “actively affiliated with his former, undesirable associates” and plotting to escape.
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“Notwithstanding our patient efforts to counsel Bulger toward constructive program participation, he is becoming more sullen, resistive, and defiant by the day. We do not believe we can return him to the population here without inviting further serious trouble.”

Bill Bulger showed up unexpectedly at Bennett’s Washington office on November 12, 1959, hoping to make a personal appeal on his brother’s behalf.
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Bennett was not available and it was already too late. Whitey had just set off on the first leg of his trip to The Rock.

The only thing about Alcatraz
that reminded Whitey Bulger of home was the name they gave the corridor near the row of cells where all newcomers were held. They called it Broadway. In this hard new world, his arrival drew no special notice. Al Capone, George “Machine Gun” Kelly, and “Birdman” Robert Stroud had been among the most notorious inmates to ever call Alcatraz home. Whitey Bulger was just another bank robber, inmate 1428—and he wasn’t even the only Whitey in the place. There were two others with the nickname.

Jim Albright, who served as a correctional officer at Alcatraz from 1959 until it closed in 1963, recalled Whitey as a nondescript, “run-of-the-mill” convict who stayed out of trouble and didn’t draw much attention.
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“He’d mind his own business,’’ Albright said. “He wasn’t overly friendly, but if you asked him something he’d answer you. If you said, ‘Good morning,’ he’d say, ‘Good morning.’ He didn’t stand out from anyone else.”

Whitey was relieved to discover that every inmate had his own cell, even though each one was just five feet wide by nine feet long, with a seven-foot ceiling. Standing in the middle of his cell with both arms outstretched, he could touch the walls on each side. It was furnished with a bed, a toilet, a sink, a couple of bookshelves, and two metal planks that folded down from the wall and served as a seat and table. Whitey spent most of his time in Alcatraz in cell C-314, a unit located on the top of a three-story tier that faced a wall. That didn’t give him much of a view, but it gave him privacy, which he wanted much more. No one across the way could peer in. If he stood with his face close to the bars, he could glimpse the library on the corridor to his left. Sunlight streamed through the windows on good days. The cells were wired with earphone jacks, which allowed inmates to listen to radio broadcasts approved by the warden. But if there were some amenities that hadn’t been available in the Atlanta prison, the regime was familiarly strict: Inmates were required to work eight hours a day Monday through Friday unless they were ill or sent to “the hole,” or segregation, for punishment.

Whitey went along with the work routine—his experience in Atlanta had convinced him that resisting the rules was counterproductive—but he figured out a way to game the system and earn an assignment to his liking. The man he played was Maurice Ordway, who, having joined the staff in 1934, was the longest-serving guard at Alcatraz. Ordway was ornery, with thick, beefy hands. The inmates called him Double Tough because he once told one of them, “You think you’re tough? Well I’m double tough.”
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Double Tough Ordway sidled up to the newly arrived Whitey and said, “You’re working in the kitchen.” The kitchen detail was considered one of the most taxing at Alcatraz.

“OK,” Whitey replied. “Do they have meat cleavers and big knives?”

Ordway narrowed his eyes, went to see his superiors, and was soon back at Whitey’s side with new orders: “You’re working in the clothing room,” he said.
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For all of Alcatraz’s notoriety, Whitey felt more at ease there, even though Alcatraz was, by design, filled with volatile criminals. It was, after all, the last stop for the irredeemable. “At Alcatraz you had to watch your back and you had to have somebody watch your back,” said Sunday, who was transferred to Alcatraz for fighting in Atlanta and arrived about a week after Whitey. “Jimmy watched my back and I watched his.”

On weekends and holidays, prisoners were allowed into the recreation yard, where there was a baseball diamond and bleachers. They could play baseball, handball, horseshoes, chess, checkers, or dominoes, and they could lift weights. Whitey had never much liked team sports,
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so he spent most of his time pumping iron and occasionally playing handball. Some days he would climb to the top of the cement bleachers and look longingly at the San Francisco skyline and the Golden Gate Bridge.
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The sound of women’s laughter could sometimes be heard coming from boats cruising by the island. And, when the wind was just right, the smell of chocolate baking across the bay at Ghirardelli’s occasionally wafted past. The sights and smells, tantalizingly close and yet so far away, inspired hope even in those serving long sentences. “We’d talk about what we wanted to do when we got out,” Sunday said.
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“A lot of us were just dreamers.”

Reading was a favorite pastime for many inmates, who had access to a library of fifteen thousand books and seventy-five popular magazine subscriptions.
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Prisoners were not allowed inside the library but could order books from a catalogue. Whitey forged a close friendship with Clarence “The Choctaw Kid” Carnes, a Native American from Oklahoma who worked in the library and delivered books—sometimes with chewing gum or cigars tucked inside—to the cells on a pull cart. By the time Whitey arrived at Alcatraz, Carnes was already a legend. At eighteen, he became the youngest inmate ever sent to Alcatraz after he was convicted of murder and kidnapping and made a couple of escape attempts. In 1946, he was involved in a violent escape attempt in which three inmates and two guards were killed—resulting in an additional sentence of life in prison. The Choctaw Kid wasn’t going anywhere soon.

Whitey considered many of his fellow inmates on Alcatraz intellectually superior to the domino-playing gossips in Atlanta, and there is evidence that they were. A Bureau of Prisons booklet published in 1960 reported that Alcatraz inmates “read more serious literature than does the ordinary person in the community. Philosophers such as Kant, Schopenhauer, Hegel, etc., are especially popular and their books have a wide circulation. Advanced mathematics and physics texts, too, are in great demand, as are other types of literature having to do with more profound aspects of our culture.”
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The Rock proved a safe and quiet place for Whitey to grow into his intellect and hone his views. He read books about military history, war, philosophy, and politics and was fascinated by Machiavelli, the Italian political philosopher who espoused using brute force, deceit, and illicit means to achieve power.
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They were lessons he would live by. He also studied Spanish, though without ever attaining much fluency. “He reads voraciously and his choice in reading is very good,” an Alcatraz staffer noted.
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“He composes some poetry also and these outlets he says afford him a means of escapism.”

Whitey the poet—it is something remarkable to contemplate, but, sadly, none of his compositions has survived. He wasn’t, Sunday recalled, serious about his writings, dismissing them as simple rhyming verses that weren’t very good. But he knew what he liked in a poem, and was so impressed with one that Sunday wrote in prison called “The Ballad of Billy the Kid” that he asked for a copy and kept it tucked inside his Bible.
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Whitey was generally well liked by other inmates and was more sociable than he had been in Atlanta, but he did not get close to many people and seemed, to his prison acquaintances, always on guard.
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“He was a very nice guy if he liked you,” said Robert Schibline, a convicted bank robber who served time on Alcatraz with Whitey. “But he kind of kept a low profile like he was expecting people to fuck with him.” Two months after his arrival, Whitey wrote a surprisingly upbeat letter to Rev. John O’Shea, a priest and South Boston native who had befriended him when Whitey was in the Atlanta penitentiary. Whitey told the priest his incarceration had been hard on his family and especially on his mother. She had expected him to be imprisoned somewhere closer to home. Whitey wrote her letters to cheer her up, but the anguish he caused his family left him bitter.
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