Free Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice by Kevin Cullen Page B

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. 25 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, 26 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.” 27
    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.” 28 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. 29 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.” 30 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. 31 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. 32 “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. 33 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