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Stephen and Julie Rakes had only recently opened their South Boston liquor store when James “Whitey” Bulger decided he wanted it. They told him it wasn’t for sale. He and his associates threatened the family until they surrendered the business. The address is 295 Old Colony Avenue, where Rotary Liquors appears in Boston’s licensing records today. Before that name, it was associated with Stippo’s Liquor Mart and the South Boston Liquor Mart, a business that became part of Bulger’s criminal operation. The story behind Whitey Bulger’s liquor store involves more than a gangster meeting place. It also involves a family who sought police help and an FBI agent who passed information to the man threatening them. The liquor store the owners didn’t want to sell Stephen Rakes and his then-wife, Julie, opened Stippo’s Liquor Mart in 1983. In January 1984, Bulger, Stephen Flemmi and Kevin Weeks went to the Rakes home to acquire it. The federal appeals court’s account of the takeover describes Rakes refusing both a sale and an unwanted partnership. Bulger responded with a death threat. The men returned later that evening with weapons. Flemmi picked up the couple’s young daughter while threatening her father’s life. Bulger handed Rakes roughly $65,000 and promised another $25,000. The gangsters treated that payment as making them the owners, despite the family’s refusal to sell. The pressure continued afterward. The family briefly fled to Florida, then returned and tried to hold on to the store. They eventually signed it over. The request for help that reached Bulger Julie’s uncle, Joseph Lundbohm, was a Boston police detective. When the couple asked for help, he approached FBI agent John Connolly. Connolly was handling Bulger and Flemmi as informants. The information Lundbohm brought him should have prompted an investigation into the threats. Instead, the federal court’s findings in United States v. Salemme describe Connolly failing to record the report or alert his supervisor, then telling Bulger about it. Bulger subsequently pressured Rakes to have Lundbohm back off. The family’s attempt to obtain protection had reached the person they needed protection from. That detail explains why this address matters beyond its association with Bulger. The store’s takeover was also an example of the protection his corrupt relationship with an FBI agent afforded him. The court found that the FBI did not investigate the extortion of the Rakes family. Before the liquor store, there was a garage Bulger and Flemmi had previously conducted business at the Lancaster Street Garage, 131 Lancaster Street, in Boston’s West End. The West End Museum’s history of the garage describes bookmakers delivering payments there after Bulger’s rise within the Winter Hill Gang. George Kaufman owned the business, officially called Lancaster Foreign Motors. Massachusetts State Police bugged the building in 1980 and watched its visitors from across the street. Bulger and Flemmi learned that the location was under surveillance and stopped using it for a time. The garage and the liquor store were different addresses serving a similar purpose: functioning businesses that also provided places for the gang’s activities. The sale agreement appeared at Bulger’s trial Decades later, the liquor store appeared among the exhibits introduced at Bulger’s 2013 trial. GBH’s collection of trial evidence identifies an agreement selling the South Boston Liquor Mart to Kevin Weeks, with Bulger named as a silent partner. It also identifies the business as Stippo’s. That document connects the names readers encounter in accounts of the property. Stippo’s and South Boston Liquor Mart refer to the business involved in the takeover, while the agreement placed Weeks in the transaction and identified Bulger’s interest behind him. What is at 295 Old Colony Avenue today? A Boston Licensing Board notice for May 2026 lists Rotary Liquors at 295 Old Colony Avenue, South Boston, operated by Mahabali Corporation. The notice concerns a request to change the manager of its retail alcohol license. The current business has a different name from the store described in the historical records. Its presence at the address should not be taken to suggest any connection between its present operators and Bulger’s crimes. For other addresses connected to Boston’s organized-crime history, our article on 4 Boston-area gangster hangouts covers the North End and Somerville locations separately.
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