First boss of the Winter Hill Gang. Born 1929. First came to public prominence in 1961, when he was arrested in October 1961 for the murder of Charlestown mob boss Bernie McLaughlin, after McLaughlin tried to wire McLean’s family car with explosives. Their feud had started after several Somerville gangsters badly beat Bernie McLaughlin’s younger brother, Georgie, at a Labor Day 1961 party in Hampton Beach NH. After Bernie’s murder full-scale war broke out in the Boston underworld, only some of which was related to the battle between the Somerville and Charlestown mobs.

According to Frank Salemme, Buddy was an early FBI informant, recruited by H. Paul Rico. In 1964, Ron Demody, a member of Whitey Bulger’s old bank-robbing gang, was fresh out of federal prison. He took a shot at Buddy, missed, and then called Rico to set up a meeting. Rico set up a time, then called Buddy, who appeared on the Watertown-Belmont line and gunned down Dermody.

By October 1965, the McLaughlins had been scattered, and Buddy was on top of the non-Mafia rackets. But as he left a barroom on Winter Hill, one of the remaining Charlestown hoods, Stevie Hughes, let him have it. He was hit in the head and died a few hours later. Control of the gang passed to Howie Winter.

Does he or does he not resemble young Rep. William M. Bulger?