Early Life
Connolly was born and raised in Roxbury, Massachusetts, USA, the hometown of Stevie Flemmi. He is the youngest of three children. His father is Irish-American and his mother is Italian (Sicilian). Like Flemmi and several other members of the Winter Hill, Connolly grew up in the Orchard Park projects, one of the first low-income housing projects in Boston. At age 12, Connolly's family moved over the city line into a working class section of Milton, a wealthy suburb of Boston. At age 15, Tim Connolly befriended a high school classmate, Billy Hussey, Stevie Flemmi's biological son. Connolly met "Stevie" and their relationship grew from there. Flemmi would ultimately become Connolly's mentor and boss for the next three decades.
Connolly graduated from Milton High School in 1976, where he was captain of the basketball team, earning all star honors. He attended Bridgeton Academy, Maine for a post graduate year. In September 1977 Connolly entered Boston College on a partial basketball scholarship. He quit before the season started. Connolly graduated from BC in 1981.
Read more about this topic: Timothy A. Connolly 3rd
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