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Metro

Whitey Bulger cooperated with FBI as early as ’50s

A mug shot of Whitey Bulger from 1956.

A federal prison mug shot of Whitey Bulger from 1956.

When he graduated from penny ante crime to the big leagues of bank robbery, James “Whitey’’ Bulger learned a hard lesson early on: Everybody talks.

And so he decided to play the game, too. Not to keep himself out of prison, as he did in his later notorious role as an informant for the FBI, but in a complicated scheme to exact revenge against some criminal associates.

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Facing charges on three bank jobs in 1955, he willingly made a written statement, naming his two accomplices in one of the heists.

He only verbally identified his accomplices in the two other bank jobs, but persuaded his girlfriend, Jacqueline “Jacqui’’ McAuliffe, to formally identify them to the FBI.

“As a result of her cooperation,’’ FBI Agent Herbert Briick wrote in a July 13, 1956, report, “process was obtained for Bulger’s accomplices’’ in those two robberies.

Bulger pleaded guilty to the three jobs and got 20 years; McAuliffe got a pass. But, more importantly to Bulger, his role in snitching on his accomplices was never made public.

Bulger’s actions, revealed in previously undisclosed prison files, reflect an early aptitude for negotiating the complex world of snitching on criminal associates and show the beginning of his transformation from local hoodlum to cross-country gangster.

WBUR first reported Wednesday that Bulger had identified his accomplices in the bank robberies. The Globe independently corroborated that report, as well as why he was willing to turn on his accomplices in the first bank robbery: He believed one of them, Carl Smith, had gotten him arrested.

The entire episode provides new insight into how Whitey Bulger learned to use cooperation with the FBI to gain leniency and why he was so obsessive about insulating himself from potential informants, even as he worked for years as an FBI informant.

The records also show that, once in custody, Whitey Bulger came to rely on his family’s political connections, first to make his time in prison more palatable and then to win parole. Central to those efforts was their congressman, John McCormack. McCormack was majority leader when Whitey went into prison and speaker of the House when he came out. Prison records show that McCormack’s influence helped authorize family visits to prisons and eventually win parole. McCormack wrote regularly to James Bennett, director of the Bureau of Prisons, on Bulger’s behalf, and records show McCormack’s advocacy usually got results.

Another influential advocate for Whitey Bulger, helping to ease his stay and win him parole, was the Rev. Robert Drinan, then dean of Boston College Law School and later a Massachusetts congressman. Drinan was Bulger’s prison pen pal, spiritual adviser, and later, parole adviser. Whitey’s brother, William, would later study under Drinan and regularly enlisted McCormack’s assistance on his brother’s behalf.

In a letter Bulger wrote to Drinan, but which prison authorities in Atlanta refused to deliver to the priest on the grounds it could jeopardize security, Bulger asked Drinan if he had a legal right to get a transfer from his eight-man cell. He had checked himself into the prison’s psychiatric ward after enduring three months of what he called “continual idle chatter on sex, cars, money, etc.’’

“I then saw the Pyscho. Dr. and explained that I couldn’t stand the 8-man cell and if any one of them bothered me any more I wasn’t going to hold back anything. Then my nerves were all shot and I kept myself out of trouble by hoping they would help me out of there.’’

Bulger agreed to cooperate with the FBI in 1956 after learning that Carl Smith, who had talked Bulger into going on his first bank job, had, as Bulger put it, “squealed on us.’’

Bulger told the FBI that he was introduced to Smith at the Stage Bar in Boston’s Theater District in May 1955. Smith asked Bulger, then 25, to drive for him in an unspecified crime. Whitey insisted to prison authorities that he was duped into his first bank job.

“When he learned that this deal concerned a bank robbery, he wanted to back out, but did not want them to know he was afraid,’’ a prison official wrote. “He claims that he was even more afraid when he learned he had to go into the bank since two persons who [were] involved backed out. He stated that the bank robbery was successful and afterwards he was in on three more bank robberies.’’

In May 1955, Bulger walked into a bank in Pawtucket, R.I., with Smith and Ronnie Dermody, an ex-con from Cambridge. Bulger pointed a .22 caliber revolver and forced bank employees to lie on the floor. The trio made off with $42,112.

Bulger took his cut from the bank job and took his hairdresser girlfriend Jacqui McAuliffe to Florida, where they stayed at high-end hotels. McAuliffe, three years older than Bulger, looked like Jayne Mansfield and had done some modeling. She was the first of a string of beautiful blondes, first Teresa Stanley, then Catherine Greig, who would be his companions, sometimes on the run, over the next half-century.

Carl Smith had once lived in Hammond, Ind., which is why Bulger’s next bank job was there. Smith had identified a bank in Hammond as a soft touch. Smith, Bulger and another accomplice, Richard Barchard, drove out from Boston to rob it on Oct. 29, 1955, but backed off when they saw a police officer inside. As they left Hammond, Bulger and Barchard noticed another bank in town that looked like an easy mark.

They headed back east, and on Nov. 18, 1955, Bulger and a bricklayer from Dorchester named William O’Brien robbed a bank in Melrose. Bulger vaulted the counter and took $5,035 out of the tellers’ drawers. They split the money with Barchard, who had picked out the bank and cased it.

Bulger and Barchard wanted to let the heat die down. They remembered the lonely little bank in Hammond, Ind., and decided to make it a double date. Barchard took his wife, Dorothy, and Bulger brought Jacqui McAuliffe along. The boys left the girls in a motel and cased the bank, then hit it the next day, Nov. 23, 1955.

Bulger pointed two pistols that day. Barchard vaulted the counter and grabbed the cash. They made off with $12,612.

The couples split up, and Bulger and Jacqui headed for Miami. After another round of fancy hotels - Bulger claimed he had blown $25,000 on hotels and fine food in the year he was robbing banks - they came home in early December.

In the meantime, Smith had been arrested and started talking. A few days after New Year’s, authorities in Indiana issued a warrant for Bulger’s arrest based on Smith’s statements. Bulger got wind of the warrant and drove cross-country to California, the state where he would later spend most of his 16 years on the run from 1995 until his arrest last June in Santa Monica.

But he missed Jacqui and drove back to South Boston and picked her up. They drove south to Delaware, then spent the next two months on the road - Chicago, Salt Lake City, Reno, San Francisco, New Mexico - trying to stay ahead of the law. But Jacqui got homesick and asked to go home.

Back in Boston, Whitey Bulger dyed his famous locks black, donned horn-rimmed glasses, plopped a big cigar in his mouth to distort his features. But, acting on an informant’s tip, the FBI arrested Bulger at a Revere nightclub on March 4, 1956. The agent who arrested him, Paul Rico, would later be charged with helping Bulger to murder an Oklahoma businessman in 1981. And in a memo filed by the FBI to justify keeping Bulger on as an informant, Bulger asserted in 1980 it was Rico’s kindness to him and his family during and after the arrest that persuaded him to become an FBI informant in the 1970s.

Barchard, now 81 and living in Florida, said he was unaware that Bulger had cooperated against him, but had no hard feelings for what happened more than 50 years ago.

“All I know is that Whitey and I were friends,’’ Barchard said during a telephone interview. “We committed a crime. We paid for doing the crime. He went his way, and I went mine.’’

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