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.