From King of Southie to King Rat

By Dick Lehr
Globe Staff / July 21, 1998
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Not so long ago, Whitey Bulger had people lining up for an audience with him in his native South Boston.

They came looking for help when a daughter was being bothered by a former boyfriend, or a son was looking for a job, or even when a car was stolen.

"He had more people coming to him than were going to church for confession," said a close friend of Bulger's.

But those days are gone. Whitey Bulger is no longer the boss of South Boston, the man whose very name instilled fear and awe.

In fact, one former Bulger associate now grouses, "He was King Rat. . . . If I was one of Whitey's boys, I would have left this town a long time ago because I'd be embarrassed."

In the year following the federal government's confirmation that Bulger led a double life as a crime boss and an FBI informant, people are now talking about him in ways they never would have before. With Bulger on the run, and his mythical stature all but shattered, lips are loosening about the legendary gangster, his style, and his everyday habits. Even if many still insist their identities not be revealed.

Bulger turns 70 next year, a gangster with cold eyes best known for his controlling manner; a "neat freak" who hates germs; an ardent reader; a "criminal genius." He is private to the point of being antisocial, while his sidekick, Stephen "The Rifleman" Flemmi, is sociable and charming, recall those who know them both.

"Stevie was always a good friend to me. He was good to me when Howie was away," says Ellen Brogna, wife of Howard T. Winter, the still-imprisoned and erstwhile leader of the Winter Hill gang of Somerville, which Bulger and Flemmi eventually took over, expanded, and made their own. "Whitey is another story. I stayed clear away from him."

Back in the late 1970s, Brogna recalled the time she blocked Bulger's car in a driveway, and Bulger quickly became incensed when he fumbled around trying to move her Mustang, unaware of a switch to release the car keys.

"It was freezing cold and it took him awhile to get the keys out, and he came back all flustered," she recalls. "I said, `You'd think you'd have some common sense to know there'd be a switch.' He just glared at me. I told Howie he was the most frightening person I'd ever met. He scared the heart out of me. It was like looking at Dracula."

Though some mentioned his sharp wit, others wondered about the Bulger sense of humor. "There were a bunch of us up on the roof of the Rusty Scupper watching the tall ships," says Winter himself in a telephone interview from prison, recalling a party during Boston's bicentennial celebration. "All of a sudden there is a girl screaming." Winter said Bulger was pretending he was going to throw her off the catwalk. "I was a little embarrassed."

Over the years, Bulger and Flemmi moved their base from Marshall Motors in Somerville, to the Lancaster Street garage in Boston near the old Boston Garden, to the South Boston Liquor Mart, and to the D Street Deli. Their cars often served as a kind of mobile office, and Bulger and Flemmi were skilled at evading agents stalking them.

One favorite move was to drive onto the Southeast Expressway heading south, roar down the passing lane and then, at the last second, veer sharply to the right to take the exit leading to Squantum and their Quincy residences.

During the 1980s, Bulger's day often began at midday at his condominium in Quincy, where Flemmi or trusted associate Kevin Weeks would meet him, and they'd head into town. Bulger would eat dinner with Teresa Stanley, his longtime girlfriend, at her South Boston home, then conduct business around the city, business that often included meetings with his FBI handler, John Connolly. Then he'd head back to Quincy in the early-morning hours, where his other girlfriend, Catherine Greig, awaited him.

"He could really talk," says Stanley, still smarting over Bulger's secret romance with the much-younger Greig. "He had a way of talking people into believing what he said. He had a way of turning things around."

Stanley and Bulger were together nearly three decades, meeting when she was 25, a single mother with four children. She admits to still loving him, and talks warmly about how strict and helpful he was with her kids. But she also feels betrayed.

"I spent 30 years of my life with him, and 20 of those years he was with her," says Stanley. "He was leading a double life with me and a double life with the FBI."

Now, 23 years after Bulger and Connolly forged a partnership on an October night at Wollaston Beach, these two principal actors remain offstage at the ongoing federal court hearings exploring the FBI's ties to Bulger. For his part, Connolly has asserted his Fifth Amendment right against self-incrimination. Bulger is literally gone, a fugitive on the run since 1995 when, says Flemmi, the FBI tipped them off to their pending indictment. It's a road life he's apparently adjusted to, driving around with Greig.

"He has always compartmentalized his life," says one longtime associate -- a life full of phases: bank robber, prison inmate, crime boss, FBI informant and, now, fugitive. Besides, he's always liked to travel, taking many trips with Stanley to places like London, Italy, and Bermuda.

"He could fit in anywhere," says Stanley. "I think he could adjust to anything."

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