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The Secret Life of Whitey Bulger
  • June 26, 2014 : 13:06
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“Jimmy was very quiet and well-behaved,” Cyr told me in a television interview, “a gentleman, at least with me. He had beautiful manners and was so handsome—the blond hair and those blue eyes. You couldn’t help but notice him.”

Cyr’s boyfriend got rough with her one day in the restaurant while Bulger was there having breakfast. “Jimmy took him outside, talked to him for a second and then folded him up with four straight shots,” said Cyr, remembering how Bulger became more than just another customer. Bulger returned to his seat and told her, “That won’t happen again. If it does, I will be forced to become unpleasant.”

She started dating the older man. He took her to a cookout at Billy Bulger’s South Boston home, where she met Billy’s wife and their many kids, as well as the brothers’ mother, Jean Bulger, to whom Whitey was devoted.

“He was still living at home, taking care of his mother,” Cyr said. “I guess that’s something Irish men do.”

Other dates were not so relaxed. Twice while out with Bulger, Cyr said, they were caught in gun battles with shooters trying to take him out. “He explained he was reorganizing Southie,” she recalled. There was a mob war raging in Boston at the time, and Bulger had landed himself in the middle of it.

Cyr remembers him as an “incredible,” well-endowed lover. “First time I saw him naked, I was shocked,” she said. “I told him, ‘No way you’re going to put that in me!’ But he was very gentle. Sex was a major item for Jimmy. I mean, it was like breathing. And he had to have it when he wanted, and that meant any time I was in the vicinity.”

Inevitably she became pregnant and gave birth to a baby boy. Cyr remembers Bulger as a doting father who was crazy about Douglas, his look-alike towheaded little boy. But Bulger was concerned about the exposure having a wife and child could mean to his enemies during his “reorganizing” of the underworld. He chose not to give the child or Cyr his name and kept them as much as he could out of harm’s way. She says Bulger changed after the boy’s death. “Jimmy became very cold. He said to me, ‘I can’t hurt like this. I don’t think I can go through life just as we always have with the exception of no Douglas.’ That was the one time he mentioned his name after Douglas died.”

Eventually they drifted apart. Cyr remembers the last time she heard from Whitey was in January 1995. He called at three in the morning and told her, “There’s trouble. I’m going away for a while. But everything’s under control. I’ve got insurance, and it’s gold-plated.”

“I don’t know what kind of insurance he’s got,” Cyr said, “but I honestly believe that several of the people who are walking around should be in jail, and certainly not the FBI agent. John Connolly, they threw him to the wolves.”

Bulger is now being held in solitary confinement in the maximum-security unit of a prison in Plymouth, Massachusetts. He’s made more than a dozen appearances in federal court in Boston, shuttled in and out by helicopter or in a caravan of armored black Suburbans. He smiles and nods to the media entourage that flocks to his every appearance. He waves and greets his loyal family members, in particular his brother Billy, who shows up at every hearing. His companion, Catherine Greig, was sentenced to eight years in prison after pleading guilty to harboring Bulger. She is serving her sentence in a low-security women’s penitentiary.

Bulger’s upcoming trial is the most anticipated public airing of the biggest law enforcement scandal of our time. Through his court-appointed attorney, J.W. Carney, Bulger declared that he intends to take the stand and name names, to tell of the higher-ups within the Department of Justice who authorized him as an informant and granted him immunity. He has insisted on only person-to-person communications with his lawyers, claiming that all his calls are monitored, even the protected attorney-client calls, and asserting his belief that all law enforcement is corrupt.

But the trial may never happen. Bulger turned 83 in September. He has a heart ailment. People held in custody with medical conditions tend to die. And already the feds are making moves to ensure that the full dimension of Bulger’s complex relationship with Connolly and his superiors in the Department of Justice is never brought to light.

Upon Bulger’s return to Boston to face the charges, prosecutors handling the case announced he would not be tried for any of the offenses in the original racketeering indictment that covered the period when he was a TE informant. A superseding indictment charges him only with the 19 murders he and Flemmi allegedly committed.

The judge imposed a tight gag order on Bulger’s attorney Carney, who has complained to the court that the order prevents him from talking to potential witnesses and is hampering his ability to prepare a defense. Given the machinations on both sides, it’s fair to assume that whatever comes out during the trial—if it takes place—will be a highly attenuated version of what really happened. The judge can simply rule that areas of Bulger’s evidence the government does not want made public are irrelevant, outside the purview of the current indictment or a threat to national security. End of story.

As Connolly says from prison, “It is my understanding that the many FBI agents who have been fighting to prove my innocence have been alerted by FBI officials in Washington, D.C. to evidence indicating Whitey Bulger has exonerated me and confirmed I was framed. I was also told he has implicated my admittedly corrupt former FBI supervisor, John Morris, in additional criminal wrongdoing, which proves Morris perjured himself both in his plea agreement and at both my trials. It is my further understanding these statements by Bulger have been documented in official FBI reports, but the reports are placed under seal by the Department of Justice and have not been provided to my attorneys. This comes as no surprise in light of all the other exculpatory evidence they concealed. Bulger has always kept his own counsel, for only he knows what he intends to do. Obviously it is my fervent hope that he will be allowed to take the stand and tell the truth and exonerate me.”

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read more: entertainment, News, issue december 2012


  • Anonymous
    John should not only be exonerated by whitey Bulger but also by the entire justice departments !! Great article
  • Anonymous
    I enjoyed the article but as a friend of "a young US Marshall zeroed in on the lead" I find it odd that Playboy didn't mention his name. Neil Sullivan was THE reason that Whitey Bulger was captured. The FBI was secondary to Neils' relentless work to apprehend a fugitive and his work should be noted.