Kevin Cullen

Where trust is important, taking a pinch matters

The first time Billy Shea had a real conversation with Whitey Bulger, it was on a streetcorner in South Boston, and Whitey handed him 500 bucks.

The last time, they were standing at the bottom of the cellar stairs in the projects in Southie and Billy was so sure Whitey intended to kill him that he was packing heat himself.

On Tuesday, Billy Shea and Whitey Bulger saw each other for the first time in more than a quarter-century. They smiled at each other across the courtroom, and Billy cracked wise. He even got Whitey to laugh.


Billy had come back home, his tie as loose as his tongue, to help the government put his old pal away for the rest of his not-so-nice life.

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Billy’s 74, but back in the day, he was part of a gang of Southie hoods called the Fifth Street Crew. They would shoot you sooner than look at you.

Billy did a bit for armed robbery, but when he got out of Walpole in 1977, he hooked up with Whitey, who was looking to appease the cowboys from Fifth Street.

Whitey approached Billy, a freshly minted ex-con, and said, “I heard some good things about you.”

Good things meaning Billy could take a pinch and keep his mouth shut.


“He gave me an envelope,” Billy recalled, “and said ‘Welcome home.’ ”

When Billy opened the envelope and counted out the 500 bucks, he figured it was a peace offering.

“Jim,” Billy said, calling Whitey by his preferred first name, “had taken over South Boston and was perceived as the boss of South Boston. But he had some tension with the Fifth Street Crew while I was incarcerated.”

Whitey did more than give Billy some cash. He hooked him up with one of his guys, Jack Curran, to put some money on the street.

Billy asked Whitey for permission to open a card room, where high rollers could play poker without the fear of getting robbed.


“He didn’t charge me anything to open up a card room,” Billy said.

Billy noticed all these guys walking around Southie with big wads of cash. Marijuana dealers were everywhere. There was more grass in the gin mills on Broadway than on the fields across from the Old Harbor projects.

“I went to Jim and said I could round them up and put them in line,” Billy explained.

Whitey had noticed the same thing.

“But he didn’t want to get his image involved in drugs,” Billy said.

Still, the drug trade was too lucrative to ignore, so Billy Shea would be Whitey’s front man in it.

Billy Shea became Whitey’s beard.

Everybody went along with the charade. Guys who got ripped off would come to Whitey and explain their predicament. Nobody mentioned drugs. But Whitey would straighten everything out. And then he owned those dealers.

Billy Shea and the Fifth Street Crew would ride around town and ask dealers to get in the car. If they said no, Billy would tell them that the next time they saw him it would be dark, “and they wouldn’t see us.”

When the dealers got in the car, they saw an automatic weapon on the seat. Billy called it the Dog and Pony Show.

“I would wish them great success in their business but they had to come into our fold or they’d be out of business. We would give them product, and our prices were lower. Basically, it was intimidation. I don’t remember anyone not capitulating.”

The money they made from grass was chump change compared to the margins in their cocaine business. Whitey went from getting $4,000 a week to $10,000.

In court Tuesday, Billy told prosecutor Brian Kelly he was clearing $100,000 a week. And immediately knew he had said too much.

“I know Jim’s looking at me, ‘You son of a bitch, you made that kind of money and that’s all my end was?’ ” Billy interjected.

Whitey chuckled at that.

Asked to identify Whitey, Billy pointed to him and said, “He’s the young fella there.”

Whitey laughed.

Billy liked Whitey. Always had, even back in the day when their interests clashed. When Billy wanted to retire, Whitey wouldn’t let him. Billy took another pinch, in 1983, and kept his mouth shut. A few years later, he wanted out.

“I made my money,” Billy said. “I put it away. I didn’t live large.”

Whitey was furious at Billy for wanting to move on. So furious that he threatened Billy.

“You remember what happened to Bucky Barrett,” Whitey said.

Whitey is charged with shooting Bucky Barrett in the head and burying him in the cellar of a house on East Third Street, right near his politician brother’s house.

“You threatening me, Jim?”

It wasn’t over.

Whitey came to his house and Billy armed himself. He got into a car with Whitey, Steve Flemmi, and Kevin Weeks. They drove to a deserted part of the D Street projects.

Whitey ordered him down some cellar stairs and Billy raced in front to be able to put his back to the wall and see over Whitey’s shoulder.

“I was looking at his hands,” Billy said. “I think he took me down there to frighten me or whack me.”

Billy was prepared to shoot Whitey, knowing he would die at the hands of Flemmi and Weeks if he did. Whitey talked about their long partneship.

“He mentioned trust,” Billy said.

Billy reminded Whitey he took a pinch in 1983 and kept his mouth shut.

“The tension went out of his face,” Billy recalled.

It was over.

So was Billy’s testimony.

Whitey’s lawyer, Jay Carney, didn’t even bother to cross-examine him.

Kevin Cullen is a Globe columnist. He can be reached at Follow him on Twitter @GlobeCullen.