Loved and Feared

Mention the Winter Hill Gang and most people immediately think of James “Whitey” Bulger. But Bulger was not the founder of the gang. He was not even the second leader. That title belonged to Howard T. Winter. The gang, named after a Somerville, Massachusetts, neighborhood, came about during the late 1940s when a teenager from Somerville recruited a few of his friends to help pilfer some goods from the nearby Charlestown ship docks. The friends soon discovered how lucrative that could be. They were prepared to follow the lead of their pal in what became the Winter Hill Gang. The friend was Buddy McLean. Larry Leavitt states: “When I was a young boy, my father told me stories about Buddy McLean. I became fascinated with him. Years later, several books were published about Whitey Bulger and the Winter Hill Gang. There was never much written about Buddy, though I thought his story was much better. I mentioned the idea of writing a book about Buddy to my Dad. He said, ‘Absolutely, who better to write about.’ “Many of those with knowledge of Buddy passed away or refused to talk. Several people who agreed to meet with me demanded to remain anonymous. Sometimes they held back information, feeling like they would be breaking a code of silence. The folks who did agree to share what they knew of Buddy, provided an in-depth view of a man who stood at the forefront of a historic time in Boston crime.” During the 1950s and ‘60s, Buddy McLean had the reputation as the toughest man walking the streets of Boston. Hundreds challenged him. No one could take him. In the same time span, the young truck driver/longshoreman from Somerville began building a criminal enterprise. Years later, it became known as the Winter Hill Gang. In 1961, Buddy faced confrontation with the ruthless and violent McLaughlin brothers of nearby Charlestown. When he wouldn’t concede to them, a feud started. More than sixty people died. From those who knew Buddy McLean best, this is his life story.