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‘Whitey’ The Kid: Bank Robber, Fugitive And Snitch In The ’50s

First in a two-part series. (Update: Here’s Part 2.)

We have known since the 1990s that James “Whitey” Bulger was a secret FBI informant going back to the ’70s. But thanks to newly obtained government documents, we now know Bulger started snitching on fellow criminals back in the 1950s.

Bulger’s career would culminate with the corruption of the FBI and alleged murders of criminal informants following tips from agents who protected him. In all, Bulger is charged with 19 murders, although former associates say Bulger claimed to have killed far more than that.

As the 82-year-old Bulger heads toward a trial set for November, we have made some surprising discoveries about Bulger at age 26.

‘Take My Hand, I’m A Stranger In Paradise…’

BOSTON — You want to put the era in perspective? Tony Bennett was young. The song “Stranger in Paradise” was new. That year, 1955, was closer in time to the Spanish-American War than to this November’s trial date. And “Sonny” Bulger, as some people still called him, was stealing from the backs of trucks.

“Whitey’s in his mid-20s,” said former Boston Globe reporter Dick Lehr. “And tailgating is the stuff of teenagers.”

Lehr and his fellow former Globe reporter Gerry O’Neill are writing the biography of James Bulger.

“He’s got to move on to the new big thing, and at the time in the ’50s, bank robbery was where the action was,” Lehr said.

Starting that May, Whitey and his accomplices robbed banks in Pawtucket, Melrose and Hammond, Ind. He jumped onto bank counters, never bothered with a disguise, and pointed two guns when ordering everyone to the floor.

“It was one night in 1955, the first time I ever ran into Whitey,” recalled retired Boston Police Detective Eddie Walsh. In 1955 he was a rookie cop; he’s 90 now.

“Him and Stevie [Flemmi], they were bad guys, you know,” Walsh said. “They were vicious guys, boy.”

Bulger The Snitch

Steel-hard, stand-up, contemptuous of weakness, the last person in the world to ever rat someone out. Bulger’s persona was forged of this for decades, until the late 1990s, when federal Judge Mark Wolf blew the image to bits by exposing Bulger as a protected, secret FBI informant set loose in the ’70s.

But FBI files and prison records recently obtained by Lehr and O’Neill reveal that Bulger began ratting people out in 1956. I showed the files to Kevin Weeks, Bulger’s surrogate son.

“Does it surprise you,” I asked him, “that even back then he was ratting people out?”

“You know, if you had asked me that prior to the indictments of ’94, ’95, I would have said ‘never,’ ” Weeks said.

But it’s still news to Weeks that Bulger began snitching the same year Kevin was born. Weeks smiles at what the files reveal about the clever machinations of his former boss. They involve the young Bulger’s Machiavellian use of his own girlfriend to get out of a jam.

Bulger had been a lady’s man for a while, but now he was a bank robber and a lady’s man, and he had a woman with him, a girlfriend two years older named Jacquie McAuliffe, who lived in Southie.

Bulger's former girlfriend, Jacquie Martin, died in 2010 (Courtesy)

She read the FBI description of her in a 1956 warrant for his arrest: “Five foot, six inches, 118 pounds, blue eyes, platinum blonde hair, very attractive, model-type.”

When the usually tight-lipped FBI is moved to employ an adverb, as in “very” attractive, you know she was striking.

“They are believed to be riding in a 1951 Oldsmobile 98,” the warrant continues.

Jacquie and Jim traveled as Mr. and Mrs. Bulger. Back in Southie her married name was Martin and she had a 6-year-old daughter. Out on the road as Mrs. Bulger, she acted as a lookout from the backseat, according to the FBI, while Bulger and an accomplice named Richard Barchard robbed the Hoosier State Bank in Hammond, Ind., in November 1955. The outlaws celebrated in Chicago, but by January the FBI had a warrant for Whitey’s arrest.

“If located, hold car and occupants… James J. Bulger is considered to be armed and dangerous,” states the warrant.

Jacquie was now riding shotgun to a fugitive. She wasn’t exactly Bonnie to his Clyde, but soon she would be doing his dirty work.

A good-looking, platinum blonde from Southie who loved dogs and a wanted man. Sound familiar? Forty years before dog-loving, attractive, platinum-blonde Catherine Greig of Southie rode off with Bulger on his second fugitive run, in 1996, there was Jacquie McAuliffe Martin.

Weeks, who had long observed this same female fascination for his boss, laughs again.

“They make movies about things like that: girls being attracted to the bad boy — the flash, the lifestyle, the money,” he said.

Indeed, one of the enduring memories of Jacquie shared by a couple of Bulger’s friends was of being called off their stoop in Southie one day in the mid-’50s and over to Bulger’s car. In the backseat sat Jacquie draped in furs, the high-fashion flame of an uncaught bank robber who had a lot of disposable income.

Now that he was wanted, Bulger’s hair was dyed black, perhaps by Jacquie, who listed her occupation as a hairdresser. Jim burned up the blacktop across the country with his platinum “paramour,” as the bureau put it in the quaint language of the day.

On the car radio, they might have heard Tony Bennett singing, “Somewhere in space I hang suspended,” from his his song “Stranger in Paradise.”

Bulger’s run to freedom that first time lasted just three months. In March 1956, FBI agents brought it to an end in Revere, where things often ended for mobsters. Jim went to jail and started snitching. Jacquie went to South Boston, but she would soon come back in a role as supportive as Catherine Greig would later play.

Cooperating With The FBI

“Bulger, after his apprehension, cooperated with this bureau,” part of a written in an FBI report in July 1956.

Bulger admitted his own role and then told the bureau who his accomplices were in the two bank jobs that were still unsolved. But Bulger didn’t want it on paper.

“He made these oral admissions but insisted that it not be put in writing,” Lehr said.

The reason why is simple, said Weeks: “So that way there was no written statement or signature by him.”

“So nobody can say he’s ratting people out?” I asked.

“Correct,” Weeks replied.

Yet Bulger made sure the FBI got the names of his accomplices on paper. And here’s where Jacquie, the blond bombshell, comes back into the story: Whitey gives her up! That way she does the dirty work for him. After all, she had been along for the ride and she knows who Bulger’s accomplices were. Weeks, who was Bulger’s prize pupil, has it all figured out.

“The girl makes a written statement so nothing can be attributed to him,” Weeks said. “He still has his reputation. No one can prove he’s the actual one who gave up the two other people. It looks like it was her.”

According to the FBI report of July 13, 1956, which would have been confidential, Bulger persuaded Jacquie “to cooperate with the bureau. As a result of her cooperation, process was obtained for Bulger’s accomplices.”

‘I Thought We Were Friends’

Soon the FBI grabbed them, too. One of them was named William L. O’Brien. The other was named Richard Barchard. O’Brien was murdered back in the ’60s, but I tracked Barchard down on the Gulf. He was far away, but wishing he was even farther.

Fifty-six years after the fact, I broke the news to him. I put it this way: “Would it surprise you if I told you she [Jacquie McAuliffe] was the one that gave you up to the FBI?”

“I respected him. He respected me. I didn’t think he would ever run his mouth, but I guess he did.”
– Richard Barchard,
ex-Bulger accomplice

“I don’t know who gave me up,” he replied. “But I mean, it’s so long ago that it doesn’t matter really.”

I read Barchard the FBI report. He’d done 10 years in prison. He’d gone to the notorious penitentiary at Alcatraz — “The Rock,” “Super Max” — because Bulger used Jacquie to give him up.

He remembered Jacquie well. After all, she was in the car acting as a lookout with Barchard’s wife, Dorothy, back in November 1955, when Whitey jumped atop the counter with two guns and Barchard jumped over the counter to collect the money.

I tried to imagine Barchard hadn’t ever figured out that Bulger ratted him out.

“Well I’m sorry to hear that,” Barchard replied. “Because he didn’t give me the impression he was that type of guy.

“Whitey and I got along good,” he continued. “I respected him. He respected me. I didn’t think he would ever run his mouth, but I guess he did.”

That got a laugh from the 81-year-old, then a sad reflection.

“It’s too bad, ’cause I thought we were friends.”

That’s a line a lot of people apparently didn’t live to repeat. Bulger is charged with murdering 19 people, and Weeks told me Bulger claimed to have murdered twice that number.

It was 1956, and out on their cross-country run, or in prison, Bulger probably heard the Platters on the radio singing their Doo wop wonder, “Oh yes, I’m the great pretender.” It was a hit song and it could have been his. Whitey wasn’t yet a star, but he was already a snitch. The pattern was set.

For the outlaw and girlfriend, it was sunset — “Canadian Sunset,” as another hit song would have serenaded them. They’d done New York, Miami, New Orleans, the Gulf Coast, Chicago and then California.

Have you heard of that itinerary before? It was the same pattern Bulger would repeat with the Jacquie 2.0 — Catherine Greig, in 1995.

Even sneaking back to Southie to pick up Catherine before hitting the fugitive road in 1995 was the sequel to picking up Jacquie for the same run in 1956. Only Jacquie was a white-haired grandmother now.

“Ever talk to the FBI?” a cop on her doorstep asked the white-haired Jacquie when she was in her 80s. “No, you’re the first,” she said. “I’ve been expecting someone to show up.”

She could have given the bureau some tips. She could have told them how much Bulger loved California. She could have played “Where’s Whitey” with them. After all, she had been there with him at the start, half a century ago.

And then Jacquie too was gone, more surely than any fugitive. She passed away in December 2010, when the world wondered if Whitey was dead or alive. By the time Bulger was cuffed, along with Catherine Greig in June 2011, Jacquie had joined most of those who were living when Whitey started making patterns in 1955.

In part 2, we look at newly uncovered documents that show that Bulger had connections to powerful Massachusetts political leaders in the 1950s, long before Bulger’s brother, William, became politically prominent himself.

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