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Donald Killeen (September 14, 1923 – May 13, 1972) was an Irish-American mob boss who controlled criminal activity, primarily bookmaking, in South Boston, during the 1960s and 1970s.

The Transit Cafe

Killeen owned and managed a bar called the Transit Cafe on West Broadway in South Boston. The Transit Cafe would later be taken over by James J. Bulger and managed by Winter Hill Gang mob associate Kevin Weeks. His organization included Whitey Bulger and William S. O'Sullivan. He engaged in a turf war with South Boston's Mullen Gang.

Personal life

Donald was the second born of five brothers, including Kenneth, Edward, and George. His two brothers, Edward and George, followed Donald into a life of organized crime. His brother George was the first brother to be murdered, found shot to death in the North End neighborhood in 1950. His murderers were never discovered. In 1971 when an associate chewed off the nose of Michael (Mickey) Dwyer, rival Boston gang member and former brother-in-law of Boston Police Department Commissioner Francis (Mickey) Roche, he wrapped it up with a cocktail napkin and sent it to Boston City Hospital in a cab to Dwyer to be reattached. Donald's other brother, Edward, was found shot to death in 1968; it was listed by the county coroner as an apparent suicide. In 1968 he became a father to a son.


He was killed outside his home in suburban Framingham, Massachusetts, on May 13, 1972, as he was called away by an associate on his son Gregory's fourth birthday. He left the house saying he was going to fetch a newspaper but in reality was going to get his son's present, a toy fire engine, in the trunk of his 1971 Chevrolet Nova. As Donald went to fetch a gun stashed underneath the driver's seat of his car, a gunman pulled open the car door and jammed the machine gun in his face before squeezing off fifteen rounds.

Bulger was accused of the murder by longtime rumor. However, former Mullen gang member Patrick Nee stated that the murder was actually committed by Mullen enforcer Jimmy Mantville.


The last and youngest brother Kenneth was jogging past a parked car with four men in it in the City Point neighborhood of Boston. A voice called him over to the car and said, "It's over. You're out of business, no more warnings", as a threat to not try and avenge his three brother's deaths or continue their rackets. Kenneth would later testify at the trial of John Connolly that in the car were James J. Bulger, Stephen Flemmi and John Martorano.