The Winter Hill Gang
During the early 1970s the Winter Hill gang – named for the Winter Hill neighborhood of Somerville – took over several gambling operations run by rivals by killing their operators. Afterwards, inept management of the operations by its new owners caused the gang to lose, rather than gain, large amounts of money. By the late 1970s the gang was forced to borrow money from the Italian Patriarca crime family and to raise enough money to pay the interest on the loans the gang began fixing horse races at tracks in New England.
FBI investigators built a case against most of the members of the Winter Hill gang, including Bulger and Flemmi, and Massachusetts State Police also were preparing indictments against them. Prosecutors were persuaded not to indict either Bulger or Flemmi (by John Connolly) and they were named as unindicted co-conspirators when more than two dozen of the Winter Hill gang were charged with racketeering for fixing races. With nearly all of the Winter Hill gang behind bars, Bulger and Flemmi took over the remnants.
Having seen the cost of gambling operations and their potential pitfalls, Bulger disassociated himself and the gang from directly operating gambling, and focused instead on protection of other bookmakers and numbers rackets. He also shook down and intimidated those gamblers who did not avail themselves of his services. Bulger and Flemmi continued to feed information to the FBI and enjoy its protection as they developed cases against the Patriarca family. By the mid-1980s the Patriarca family had been all but destroyed by the FBI investigations into their operations, leaving the door open for Bulger and Stephen Flemmi to control all of the organized crime in Boston.
During the 1980s, while working with Connolly, Bulger was personally involved in several more murders, including the icepick stabbing of Louie Litif, a bookmaker and cocaine dealer. Bulger was widely believed by mob associates to have carried out this murder himself, stabbing the victim with the icepick and then shooting him in the mouth, after which the body was stuffed in a trash bag in the trunk of his car. The killing was in retaliation for Litif’s not paying Bulger a cut from the profits of his cocaine dealing and for allegedly committing two murders without Bulger’s permission.
Later a witness came forward to inform the FBI that he had seen Bulger and Flemmi murder Litif. The witness was a cocaine dealer who offered the information to the FBI in return for an opportunity to enter the witness protection program. The cocaine dealer was named Edward Halloran, known on the streets as Balloonhead, and also had information linking Bulger and Flemmi to the murder of Roger Wheeler. FBI agent Connolly and his supervisor John Morris ensured Bulger was informed of Halloran’s dealings with the FBI.