What Winter Hill Thinks of Whitey

Posted June 29, 2011
By Chris Orchard

If you grew up in the Winter Hill neighborhood of Somerville during the 1960s and 1970s, chances are you’d have fond memories of more innocent times, despite the gangland slayings that occurred every once in a while in your neighborhood.

In 1980, Sal Sperlinga, a Winter Hill Gang member, was shot dead in Magoun Square. If you ask Somerville residents, it was because he wanted to keep a drug dealer out of the neighborhood.

Today, Somerville's mayor, Joseph Curtatone, 45, remembers that incident because as a young teenager he was taking guitar lessons on Washington Street when, suddenly, heavily armed law enforcement officials stormed the area to arrest Sperlinga's convicted killer, Dan Moran.

But beyond that, said Curtatone, gang-related incidents weren't really prevalent.

"You didn't hear anything about Whitey Bulger growing up," he said.

Whitey Had Nothing to do With It

 Ask people from Winter Hill, Somerville, about "Whitey" Bulger and the Winter Hill Gang.

The first response you're likely to get is a dismissive wave of the hand, accompanied by a shake of the head.

You see, Whitey Bulger was from South Boston, they'll tell you. He had nothing to do with Somerville.

Yes, there was the Winter Hill Gang. They operated out of a garage on Marshall Street, now a church, and they hung out at a bar on Broadway called Pal Joey's, now the Winter Hill Bakery. And in 1965, the gang's then leader, James "Buddy" McLean, was gunned down across the street from Pal Joey's, in front of the Capitol Theatre, now the site of a vacant Star Market supermarket.

But none of that had to do with Whitey Bulger.

"They keep embellishing it," said Winter Hill native David Pignone of the connection between Bulger and the Somerville neighborhood.

"It's a shame that he's tarnished Somerville with his reputation," he said of Bulger. "He was not the Robin Hood they made him out to be."

Fond Memories of the "Gentlemen" of Winter Hill

Pignone, who graduated from Somerville High School in 1959—just before the Winter Hill Gang came to prominence in the 1960s—helped run a family business on Broadway, in the heart of Winter Hill, during that era. Today he runs Pignone's Cafe in Stoneham. It serves as an informal meeting place for Somerville natives of his generation—most who no longer live in Somerville but have moved to nearby towns.

One of the people who meets at Pignone's Cafe is Maureen Bradley Jones, who was a classmate of Pignone's and whose father was mayor of Somerville in the late 1940s.

For Jones, Winter Hill was a great place to grow up, and the Winter Hill Gang was nothing to be terribly afraid of.

"They kept The Hill clean. They kept all of Somerville clean," she said, adding that she believes the gang kept drugs out of the neighborhood.

People from Somerville, like Pignone, Jones and countless others, associate the Winter Hill Gang with Howard "Howie" Winter, who ran the gang from 1965 until the late 1970s.

Bulger had nothing to do with it.

Pignone described Winter and his crew as "great guys, never bothered anyone in the neighborhood."

"The most stand-up guy in The Hill was Howie Winter," he said.

Said Jones, "They were gentlemen."

Winter Hill: A Close-Knit Community and a Safe Neighborhood

Pignone described the old neighborhood by saying, "It was a family … everybody knew each other. Everybody respected each other."

"We never locked our doors in Somerville growing up," said Jones.

Margaret Mucci, who also grew up during that era, said, "It was like 'Happy Days.' We were very innocent kids." So innocent, she said, that "we would never swear."

"If you got in trouble in Somerville and the police picked you up, they generally drove you home," said Bob Schena, another schoolmate.

"When you talk about the good ol' days, those were the good ol' days," said Jones. 

Not Getting Involved

Walter Pero, 64, Somerville's alderman for Ward 4, which encompasses most of Winter Hill, recalled growing up in the area and hearing stories of the Winter Hill Gang. "I certainly remember their presence," he said. "If you knew what was good for you, you stayed away."

"Pal Joey's back room was like their exclusive haunt," he said. So entrenched was the gang in the community that "I actually played for the Pal Joey's softball team."

To this day, a number of people don't want to speak about these matters or use their names when talking about them, perhaps adhering to Pero's advice about knowing what's good for you.

One such man, who asked that his name not be used, recalled growing up with Winter's kids. "They were just normal kids just like us. But I will tell you this; you felt pretty safe when you hung around with the children of Howie Winter," he said in an email.

"When we were growing up in Somerville, we were aware of the gang wars that were going on, but normal everyday citizens really had nothing to do with those guys. We would talk about it but didn't get involved," he said.

Living Amid the Irish Gang Wars

Everyday people in Winter Hill may have felt relatively safe in the presence of the Winter Hill Gang, but for much of the 1960s there was an all-out war between that gang and the McLaughlin Gang from Charlestown.

The war started in 1961 when George McLaughlin supposedly tried to pick up the girlfriend of a Winter Hill Gang member, according to Howie Carr's Encyclopedia of Boston Mobsters. He was subsequently beaten up, the story goes, and when Buddy McLean refused to hand over the guys who did the beating to the McLaughlin crew, who wanted to kill them, the McLaughlins tried to kill McClean with a car bomb.

This launched an era of violence that lasted throughout much of the 1960s, during which time scores of people were killed, many, like McLean, gunned down in the open air when they left bars.

Whispered Stories

Nancy Bean, another Somerville native who meets at Pignone's, said, "I never knew anything about Whitey Bulger until I met my husband."

Her husband is from South Boston.

From him, Bean heard some stories, including one in which her husband decided to leave a bar because Bulger was there talking business. Better to leave than to overhear something that could get you killed. He told the bartender he had to use the bathroom, then went out the back and left.

There are many stories told about the old days. "Some is urban legend and some is true," according to the above-mentioned man who asked not to be named. 

One of those stories is about one of that man's childhood friends. When this friend was 20 years old, he did a favor for a local mobster, also unnamed. The friend had to sneak into the mobster's house when the mobster's wife was at home, find a particular closet, go into the closet, open a hidden compartment, collect a "duffle bag full of pistols," then deliver the bag to the mobster.

Another friend had to burn $20,000 in cash, for some unknown reason. The friend accomplished this task in a Somerville basement.

One of his favorite stories involves the 50th birthday party of one of the local mobsters.

The words "happy birthday" were written on the birthday cake in cocaine. All the partygoers had a straw, and they proceeded to snort the cocaine off the cake.

Whitey and the Winter Hill Gang

By the 1970s, the Winter Hill Gang was considered one of the most powerful criminal organizations in the state, and it had consolidated criminal operations not controlled by the Italian-run La Cosa Nostra.

Bulger became affiliated with the Winter Hill Gang in the early 1970s, and he allegedly ran Winter Hill's operations in South Boston. Then, in the late 1970s, when Howie Winter and other prominent members of the Winter Hill Gang went to prison (for fixing horse races, among other things), there was a power vacuum and Bulger allegedly stepped in to take leadership of the Winter Hill Gang.

By then, if you ask people in Somerville, the Winter Hill Gang was no more than a name, but a name that stuck. Kind of like the Los Angeles basketball team sticking with the name "Lakers" because it was once based in Minnesota, "land of 10,000 lakes."

But as Pignone said, "Whitey Bulger had nothing to do with Somerville."