Joe “Joe Mac” McDonald, one of the founding members of Boston’s Winter Hill gang, along with Buddy McClean and Howie Winter. Joe Mac was known “as a very serious man not to be trifled with under any circumstances”.
In the 1960’s Joe was part of a crew who were caught for armed robbery, he was sentenced to 12 – 18 years. In 1963 he managed to escape from jail and threatened the witness, who put him in jail as well as the cops who investigated it. He was eventually caught in 1966 in Brighton, Boston, after a shootout and chase by the police, McDonald fired off 4 shots but missed his targets.
McDonald was not afraid to do his own work, in 1971 McDonald was arrested in connection with the robbery of a valuable stamp collection. Raymond Lundgren testified against Joe McDonald and according to Steve Flemmi, in 1976 Joe McDonald travelled to California and shot and killed Lundgren on his front lawn, in front of his wife.
According to Steve Flemmi, Richard Castucci had allegedly given police McDonalds location in Greenwich Village, New York. In late 1976 Richard Castucci’s body was found in the trunk of his car, wrapped in a blanket and a bullet in his head.
In 1979 21 men, including Joe McDonald and Howie Winter were indicted for fixing horse races at race courses along the Eastern Coast of the US. In the court papers, McDonald was quoted as saying they should kill the jockey who backed out of taking bribes and dumping his body on the home straight of a race course as a warning to other jockeys who might be thinking the same.
However, McDonald went on the run from that indictment. But he remained active while on the run, meeting up with John Martorano to kill businessman Roger Wheeler in Oklahoma. Wheeler had taken over the World Jai Alai sport and it would have discovered the racket that Winter Hill were running through the company.
But even in his 70’s McDonald was no soft touch. One day he paid a visit to the South Boston Liquor Mart, where Whitey Bulger and Steve Flemmi had set up headquarters and said to them “Ive been away for 4 years and I know what you two have been up to. I get my cut, which is four million. I want it delivered to my house and I better not hear a peep”
A guy who was working inside the liquor mart overheard what happened and said when McDonald left Bulger start complaining about handing over that much cash but Flemmi interupted him and said “Joe has hitters all over the country. We have to get this money for him by tomorrow. Which they did.
Joe McDonald was indicted, along with John Martorano and crooked former FBI agent H. Paul Rico for the murder of Roger Wheeler. However both McDonald and Rico both died of natural causes before the trial went to court.