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With sobs, Bulger, Greig traded jailhouse love letters

With approval from Catherine Greig’s attorney, James J. Bulger’s lawyer visited her at a detention center in Rhode Island to deliver a letter the gangster had written to her on a legal pad. She then wrote her own letter to him.

James “Whitey” Bulger and Catherine Greig penned jailhouse love letters on a legal pad ferried between prisons by a defense attorney, who said he watched the former fugitives sob as they read each other’s words.

Speaking at a gathering of Massachusetts defense lawyers Wednesday, attorney J.W. Carney Jr. said Bulger believed prison officials would never allow him to send a letter to Greig, the former dental hygienist who abandoned her life and helped him hide out in Santa Monica, Calif., for 15 years before their capture in 2011.

Carney said he offered his legal pad to Bulger while he was awaiting trial so the gangster could write words of comfort to Greig. With approval from Greig’s attorney, Carney then visited her at a federal detention center in Rhode Island, where she read Bulger’s letter and sobbed.


She added her own love letter to the pad, which Carney said he did not read before showing it to Bulger, who also wept when he saw it.

“To me there is no regulation or law that should prevent people from expressing love,” Carney said.

Carney’s revelations, made at a meeting of the Massachusetts Association of Criminal Defense Lawyers during a discussion called “Untold Tales of the Whitey Bulger Trial,” revealed an unusual side of Bulger, who would be convicted weeks after the letters were exchanged of orchestrating a series of brutal murders that terrorized the city for years. He was sentenced to two life terms plus five years in prison; Greig is now serving eight years for harboring a fugitive.

Bulger told his lawyer that one of his greatest regrets was never marrying Greig while they were in hiding in California, Carney said. Carney, however, told the audience he didn’t want to leave the impression the convicted killer had “gone soft.”

He described how Bulger expressed murderous dislike for Globe columnist Kevin Cullen. Cullen co-wrote, with Globe reporter Shelley Murphy, the book “Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice.” Bulger was also first identified as an informant for the FBI by the Globe Spotlight team in September 1988.


For two hours at an Italian restaurant in the Back Bay, Carney and defense attorney Hank Brennan spoke about the challenge of having less than two years to prepare for Bulger’s trial on dozens of charges, including 19 murders. Bulger, 84, was found guilty of racketeering and participation in 11 murders.

At his first meeting with Brennan, Bulger put forth a requirement: that the attorney read a biography of Russian emperor “Peter The Great,” so he would better understand “the art of war” and use the lessons in Bulger’s defense strategies, Brennan said.

Brennan then spent countless hours with Bulger at the Plymouth Correctional Facility, meeting with him on all major holidays, including Christmas.

The defense team decided to approach the case as prosecutors. They aimed to put on trial the government’s narrative portraying Bulger and his former FBI handlers John J. Connolly Jr. and John Morris as examples of isolated corruption. They sought to persuade jurors that Bulger’s crimes were ignored as part of a sprawling FBI conspiracy endorsed by the highest levels of the Department of Justice, they said.

Brennan described feeling a sense of gratification when relatives of Bulger’s victims thanked him during a break in the trial for his rapid-fire cross examination of former Bulger gang member John Martorano, who admitted to killing 20 people and received a 12-year sentence in exchange for his testimony.


“After that, it was like I had a bat,” Brennan told the dozens of lawyers who listened intently to his rendition of how he tried to verbally pummel Martorano.

Brennan is representing Bulger in his appeal. They contend the trial was unfair because the judge refused to allow Bulger to tell the jury about his claim that the now-deceased federal prosecutor Jeremiah O’Sullivan promised him immunity decades ago. Carney has withdrawn from the case.

“I expect we’re going to win the appeal,” Brennan said.

During the event, Carney added another detail to Bulger’s immunity claim. He said in the 1970s, Bulger was first contacted by a South Boston priest, who asked him to help a man named “Jerry O’Sullivan” with “a problem.”

Bulger then “clocked” O’Sullivan’s movements to and from the old federal courthouse in Post Office Square and waited in an alley for a chance to meet O’Sullivan. Bulger agreed to help O’Sullivan, who then was a leader of the US Attorney’s Organized Crime Strike Force and later became US attorney, and in return, “O’Sullivan said he would not be prosecuted,” Carney said.

Carney would not name the priest, who is still living, or elaborate on O’Sullivan’s alleged plight, but during the trial Bulger told the judge that the former prosecutor gave him immunity in return for protecting him from an unnamed threat. “For my protection of his life, in return, he promised to give me immunity,” Bulger told the court.


O’Sullivan, who died in 2009, testified at a congressional hearing that he never protected Bulger from indictment. The Government Reform Committee’s report, however, found that O’Sullivan had enough evidence to prosecute Bulger in a 1978 race-fixing case but never charged him.

Bulger told his defense team from the start that he would testify at his trial. His lawyers crafted their case based on his willingness to admit to most of the murders and to running a multimillion-dollar drug operation. They had four lawyers conduct separate practice rounds preparing Bulger for cross examination, Carney said.

Three days before the end of their defense, however, Bulger decided he would not take the stand. He told Carney he had changed his mind because the judge would not allow him to speak about his deal with O’Sullivan. “He thought it was a sham,” Carney said.

Bulger’s decision sent shock waves through the defense team. Carney said he immediately called Brennan with the news. Brennan kept asking his co-counsel to repeat himself. “It was like I wasn’t speaking English,” Carney recalled.

Carney told a reporter Wednesday night that he doubts the government will ever allow Bulger to give a jailhouse interview.

However, he said a documentary on the case by filmmaker Joe Berlinger, which is set to premiere at the Sundance Festival on Jan. 18, could shed light on Bulger’s claims. The film, “Whitey: United States of America v. James J. Bulger,” is scheduled to be shown Jan. 30 at the Coolidge Corner Theatre in Brookline.


J.M. Lawrence can be reached at jmlawrence@me.com.

Clarification: An earlier version of this story did not fully describe how Bulger was first identified as an informant for the FBI. Bulger’s special relationship with the bureau was reported by the Globe Spotlight team in September 1988.