Whitey Bulger detested drunks and drank very little
himself. He felt that people who drank to excess were weak and inferior. But his personal feelings about
alcohol consumption didn't keep him from wanting a liquor store. While driving around South Boston with Stephen
Flemmi in the last week of December 1983, he spotted one he liked and decided he'd buy it. He'd been looking
for a new hangout, and Stippo's Liquor Mart on Old Colony Avenue was in a good location and had just been
renovated.Stephen "The Rifleman" Flemmi
In the first week of January 1984, Bulger and Flemmi showed up at the store owner's home. Bulger laid a
bag full of cash on Stephen Rakes's kitchen table -- $67,000 -- and informed Rakes that they were buying
the liquor store. Rakes said his business wasn't for sale, but Bulger's icy stare made him nervous,
particularly because his two young daughters were in the room.
Flemmi took a seat at the table, picked up Rakes's two-year-old daughter, and set her on his lap. He
then took out his gun and laid it on the table in front of the toddler, who immediately reached for it. She
picked it up and started to gum the butt.
According to the Boston Globe, Bulger turned to Rakes and allegedly said, "It would be a shame
not to see your children grow up."
Knowing Bulger's reputation for violence, Rakes changed his mind about selling. He called his wife
Julie, who was working at the store, and told her that someone was buying their business. Later, when Julie
got the whole story, she called her uncle, Boston Police Detective Joseph Lundbohm, to see if there was
anything he could do. Lundbohm went to the FBI, not knowing that Bulger and Flemmi were FBI informants, and
explained the situation to John Connolly. Days later, Bulger again threatened Rakes, telling him to "back
off." It was clear that he knew that the Rakeses had complained to the FBI through Lundbohm.
Connolly later denied that he'd tipped off Whitey, but he did nothing to investigate the extortion
incident, saying that Julie and Stephen Rakes refused to wear a wire or testify against Bulger and Flemmi,
making the case impossible to prosecute.
Stippo's Liquor Mart was formally sold to Kevin Weeks, a Bulger associate, and rechristened the South
Boston Liquor Mart. One of Bulger's best customers was the FBI. A receipt found at the store in a 1990 raid
showed that the store had supplied liquor for a Christmas party at the FBI's Boston office. A note
indicated that the liquor was bought by Special Agent "Dick Baker (friend of John Connolly)."
Bulger eventually acquired the Rotary Variety Store, which was next door to his liquor store. When one
of Rotary Variety's customers happened to buy a winning state lottery ticket there that paid $14.3 million,
Whitey decided that his customer needed a "partner." According to authors Dick Lehr and Gerard O'Neill,
Whitey and two of his associates took half of the winnings, which allowed Bulger to claim $89,000 a year in
income after taxes and got the IRS off his back.
The FBI failed to act in another extortion plot tied to Bulger in the late 1980s. Bulger informed a
South Boston realtor named Raymond Slinger that he had been hired to kill him, but Bulger would spare his
life for a price. Bulger and Slinger agreed to meet again, but Slinger made the mistake of bringing a gun
to that meeting, which was also attended by Bulger associates Kevin Weeks and Kevin O'Neil. When Bulger
discovered Slinger's gun, he went berserk, beating and kicking him. He ordered his flunkies to get a body
bag and told Slinger that the only way for him to save his life was to pony up $50,000. Slinger agreed to
come up with the money.
Slinger went to the FBI and told the agent who interviewed him that he would wear a wire and testify
against Bulger. The agent felt that they now had a "great case" against Whitey, but Bulger's guardian
angels came to his rescue again, and the case was dropped without explanation.
According to the
Boston Globe, a few days later Bulger informed Slinger through Kevin O'Neil that he was dropping
the price to $25,000, but "there wasn't going to be an FBI investigation."