James Robert "Buddy" McLean (January 26, 1930 – October 31, 1965) was an Irish-American mobster and the original boss of the Somerville, Massachusetts-based "Winter Hill Gang" during the 1960s. McLean was well known throughout the Greater Boston area as a tough street fighter. He accumulated injuries including several scars on his neck and face as well as a damaged left eye. A friend of Buddy once said, "He looks like a choir boy, but fights like the devil".
McLean was orphaned at a young age and adopted by an immigrant Portuguese-American family in Somerville, Massachusetts. Working as a longshoreman during his teenage years on the docks of Charlestown and East Boston, he would become close friends with future president of the International Brotherhood of Teamsters William J. McCarthy as well as a later member of the IRA.
After marrying a local nurse in 1955, McLean began to slowly amass a formidable criminal organization due to the admiration of his ability to fight along with a strong sense of street smarts. He would dominate the local underworld in northern Boston which included running numbers, loansharking and truck hijackings.
Irish gang wars
In early September 1961, two Winter Hill associates of McLean, and their friend, 22-year-old Charlestown mobster George McLaughlin rented a cottage on Salisbury Beach for a Labor Day party. Drinking with his friends throughout the day and into the late evening, McLaughlin attempted to grope one of the gangster girlfriends. Confronted by the two men, McLaughlin received a savage beating until losing consciousness. Unsure whether or not he was still alive, they dumped him at a nearby hospital and went to tell McLean what had happened.
McLean told them he would take care of it and had a talk with his friend, and George McLaughlin's brother, Bernard McLaughlin. When Buddy learned that Bernie McLaughlin wanted to take revenge and sought Buddy's help in doing it, Buddy told him his brother had been out of line and had the beating coming. Bernie McLaughlin stormed out in a rage. Later that night, McLean awoke to the sound of his dogs barking, and saw two men under his car. He went outside firing a .38 revolver, and found plastique wired to the ignition of his car. Suspecting the McLaughlin's, he began stalking Bernie McLaughlin throughout Charlestown until he found him. He killed Bernie McLaughlin walking out of the "Morning Glory" bar in Charlestown in broad daylight and in front of almost one hundred witnesses on October 31, 1961. He was originally arrested along with Alex Rocco but the witness who picked them out later recanted and they were released. Alex Petricone who was not a killer was sent out to California by Buddy McLean to stay out of the gang war. Alex started taking acting lessons, changed his name to Alex Rocco and became an actor. One of his first roles was playing Moe Greene in The Godfather movie.
Delaney and Hannon murders
McLean once used a female friend as a ruse to set up Wilfred Delaney and Harold Hannon, members of the rival Charlestown Mob. The woman enticed both Delaney and Hannon to come back to her South Boston apartment. When Delaney and Hannon saw McLean and his men in the girl's apartment they tried to escape but were quickly apprehended by the mobsters. The medical examiner later discovered during the autopsies of both men that the killers had used a butane blow torch and badly burned both of the men's genitals, allegedly to get information from them. After getting the information he needed McLean strangled them both and dumped them in Boston Harbor.
Although he was acquitted of the murder charge, McLean went to prison for two years for illegal possession of a firearm. Leading the Winter Hill Gang against their Charlestown rivals for more than two years, McLean was finally shot dead by Stevie and Cornelius Hughes as he left the Tap Royal. He was succeeded by his right hand man Howie Winter then later James "Whitey" Bulger.