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

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
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.

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."



