The Winter Hill Gang once conducted business in a Somerville garage that now welcomes a church congregation. On Prince Street, Mafia associates talked inside an apartment while the FBI recorded them. In South Boston, a couple opened a liquor store and soon found themselves being told to hand it over by men threatening to kill them.
Boston mob headquarters were a first-floor apartment on Prince Street, a liquor store on Old Colony Avenue whose owners kept saying no, and two garages, one later filmed by state police and one now used as a church.
The North End headquarters with microphones in the walls
98 Prince Street, North End
Gennaro Angiulo and his associates used a first-floor apartment at 98 Prince Street as a Mafia headquarters. From January 19 to May 3, 1981, the FBI recorded the conversations through hidden microphones, and a concealed camera outside photographed people coming and going so the voices on the tapes had faces. Those recordings became evidence in federal court. An FBI supervisory special agent later told the Senate that one slice of the Angiulo family’s numbers business was bringing in $30,000 a day.
For nearly a year before those tapes, the FBI could not get video of the address. People nearby reported suspected investigators to the Angiulos, often with a license plate, and they were usually right. Across 103 days of pictures, someone brought the brothers a new car or a new face on nearly every day. Agents hid a camera in a vehicle and changed that vehicle every evening. They were not spotted.
The liquor store Whitey Bulger refused to take no for
295 Old Colony Avenue, South Boston
Stephen Rakes and Julie Rakes opened Stippo’s Liquor Mart in 1983. Julie later used the name Julie Rakes Dammers. In January 1984, James “Whitey” Bulger, Stephen Flemmi, and Kevin Weeks let themselves into the family’s South Boston home. Bulger said they had been paid to kill Rakes and had decided to buy the store instead. Rakes said it was not for sale. Bulger said he would be their partner. Rakes refused that, too.
They were back that evening. They sat at the kitchen table, showed a gun and a switchblade, and threatened to kill him. Flemmi picked up the couple’s one-year-old daughter, stroked her hair, and said it would be a shame for her not to see her father again. Bulger handed Rakes a paper bag with roughly $65,000 and promised $25,000 more, which he later refused to pay. Flemmi said the store had new owners. The First Circuit’s account of the extortion lays out that visit.
The Rakeses held out for weeks, left for Florida, and came back still trying to keep the business. Julie’s uncle, Boston police detective Joseph Lundbohm, asked FBI agent John Connolly for help. Connolly told Bulger. Bulger then told Rakes to make Lundbohm back off, and the family signed the title over.
The store was at 295 Old Colony Avenue. Public records show Kevin Weeks bought the property. In May 1986 the building was sold to Weeks, Bulger, and another person, and South Boston Liquor Mart, Inc. was set up to do business there. The shop was also known as Columbia Wine and Spirits and by its original name, Stippo’s Liquor Mart. A federal forfeiture appeal is where the address and the 1986 company are traced.
The garage where the afternoon visitors weren’t coming for repairs
Lancaster Street, near the former Boston Garden
Mechanics had the Lancaster Street Garage in the morning. Most days around 1:30 p.m., Bulger and Flemmi arrived, Bulger in a black 1979 Chevy that he pulled into a bay, and the visitors came for them rather than for a repair. Dick Lehr and Gerard O’Neill describe that routine in Black Mass. George Kaufman, who had operated Marshall Motors in Somerville as a front for Howie Winter, ran this garage for the two of them. They had moved the meetings downtown, a short walk from 98 Prince Street and a couple of blocks from Boston Garden.
Massachusetts State Police filmed Bulger there in 1980. The Justice Department still has the footage.
The Winter Hill headquarters that became a church
12 Marshall Street, Somerville
Marshall Motors, at 12 Marshall Street in Somerville, was the garage they left behind. Kaufman ran it as a front for Howie Winter, and the back room is where Winter, John Martorano, and Bulger met. The Boston Globe described the place as the Winter Hill Gang’s office for gambling and loansharking. James Sousa was killed there in October 1974, after other gangsters worried he would talk to police about a botched plan to rip off a dentist with a fake gold sale. A mobster, remembering the room years later, said, “There was blood everywhere.”
A church bought the building in 2008. In May 2026 the Globe found it open as Greater Works Church of God Somerville. Reporter Danny McDonald went to a Sunday service and found purple seats, screens welcoming worshippers, and a mural of people being baptized in a river. Rev. Collin Green led the prayers. After the service he brought up Howie Winter on his own. “It’s changed,” he said. “It’s not that way. God is in the building.”
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