Stephen Joseph Flemmi was the eldest of three sons born to Italian immigrant Giovanni and Mary Irene Flemmi. He was raised in the Orchard Park tenement located at 25 Ambrose Street in Roxbury, Massachusetts. His father was a bricklayer and veteran of the Royal Italian Army during World War I, and his mother was a full-time homemaker. Flemmi is described by his former mistress Marilyn DeSilva as mild mannered and personable. He was a childhood friend and mentor of Richard J. Schneiderhan, who later became a lieutenant in the Massachusetts State Police.
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