Hennessey came to Holy Cross after
being All-State for two years at Brookline High School, and he made
an immediate impact. In his first game on the varsity squad
in 1960, he ran back the opening kickoff 85 yards in the season
opener against Harvard. He topped the effort later in the
season with an 89 yard return for a touchdown versus
A senior co-captain in 1962, Hennessey finished his three-year career with 1,157 yards rushing and nine touchdowns; caught 47 passes for 779 yards and three TD's; scored 98 points and ran back 29 kicks for 723 yards. He led the Crusaders in rushing in two of his three season with the varsity. His senior year efforts earned him All-East and Catholic All-America honors.
The 1963 Crusader of the Year played two seasons with the Boston Patriots after graduation and was their rookie of the year in 1965. He moved on to teaching and coaching at Brighton High School.