When Whitey Bulger took over leadership of the Winter Hill Gang, he made an executive decision: the gang would follow the Mafia model and start charging "rent" to loan sharks, drug dealers, and bookies who worked in their territories. Rather than sell drugs, make usurious loans, or run back-room betting parlors themselves, they would simply charge criminal entrepreneurs a fee for the right to stay in business. Anyone who refused would have to suffer the consequences - broken bones ofn the first warning, bullets thereafter.

Bulger also moved the gang's headquarters from Marshall Motors, a garage in Somerville, Massachusetts, to another garage, Lancaster Foreign Car Service, on Lancaster Street in Boston's North End near the Boston Garden where the Celtics and the Bruins played. State Police investigators kept an eye on Bulger's new location and noticed a steady stream of known bookies coming in every afternoon to pay tribute to Bulger. The police bugged the garage, but the conversations they picked up were oddly never about criminal activities. What the state police didn't know was that the FBI had tipped off Whitey about their investigation. Whitey's FBI handlers didn't want him jammed up with a state investigation when they needed him to bring down the mob.

Bulger took advantage of his privileged status, confident that the FBI would be looking out for him. On April 12, 1980, one of his associates, Brian Halloran, escorted a bookie named Louis Latif to Triple O's Tavern on West Broadway in Southie, where Bulger wanted to have a little talk with him. The meeting was brief. A few minutes after watching Latif enter the bar, Halloran saw Bulger and another associate haul the bookie's body wrapped in plastic out the back door. They dumped it into the trunk of Latif's car. The car and the body were later found at another location.

A year and a month later, millionaire Roger Wheeler was shot to death in the parking lot of his country club in Tulsa, Oklahoma. Wheeler, the chairman of Telex Corp. and the owner of World Jai Alai, had come to suspect that the Winter Hill Gang was skimming profits from World Jai Alai's Connecticut offices, and he was threatening to blow the whistle on Bulger and company.

Brian Halloran, a cocaine addict, had originally been asked to murder Wheeler at a meeting attended by Bulger, Flemmi, and former president of World Jai Alai John Callahan, but the job eventually went to Winter Hill executioner John Martorano. On May 27, 1981, Martorano, wearing a fake beard and a paper bag over his hand, walked up to Wheeler's car. The hitman was holding a revolver inside the bag. He shot Wheeler between the eyes.

Halloran feared that he knew too much and that Bulger and Flemmi wanted him permanently silenced. He went to the FBI and offered to tell them everything he knew about the Winter Hill gang in exchange for protection. He revealed that Whitey Bulger was behind the murders of Latif and Wheeler. But when Whitey's guardian angel John Connolly learned that Halloran was spilling his guts, he filed an informant report from Bulger, who swore that "there was no way that they [Bulger and Flemmi] would have been involved with Halloran in connection with anything, let alone murder," according to the Boston Globe. As a result, the FBI deemed Halloran an untrustworthy informant and gave him the boot. Shortly after he was cut loose, Halloran's bullet-riddled body was found outside a bar in Southie.

Three months after Halloran's murder, the body of former World Jai Alai president John Callahan was discovered in the trunk of his rented Cadillac parked in a garage at Miami International Airport.