Massucco was a three-year starter at halfback and punter for the Crusaders, earning All-East and Catholic All-America honors. He graduated as the college's all-time leader in career rushing yards (1,598) as well as holding the single season record. He served as a captain during his senior season, when the Crusaders posted an 8-2 record and he earned First Team All-America honors. After graduation he began a long career in coaching. Massucco served as Holy Cross' head coach for two years, with his 1966 team going 6-3-1. He was previously an assistant coach with the Crusaders for 11 years, in addition to serving as hockey coach, a freshman baseball and lacrosse assistant, recruiting coordinator and assistant to the athletic director. Massucco also served as the head coach at Worcester Polytechnic Institute from 1967-1977, and was a color commentator on Crusader football radio broadcasts. He passed away in 2002.