McDonald was a veteran World War II, and a charter member of the Winter Hill Gang, he made the FBI’s Ten Most Wanted List after a stamp robbery. He was born in Somerville, Massachusetts to Scottish-Irish immigrants from Bishopbriggs, near Glasgow. During his lifetime he was known as a tough bar-room brawler but also a "stand up guy" who was loyal to his friends. One of the originators of the Winter Hill Gang, he was close friends with gang leader James "Buddy" McLean. He was a close friend of Stephen Flemmi due to his military stint during the Korean War. He had refined his marksman skills in World War II and was an efficient contract killer. He was the oldest member of the Winter Hill Gang. He was a long-time alcoholic. He married and was the father of one daughter and one son. In 1965, a