Benn is a graduate of Governors Academy where he lettered for 4 years in both baseball and hockey. He also earned the Bruins John Carleton award given annually to an Eastern Mass student athlete combining exceptional athletic skills and academic excellence. Benn proceeded to Boston College playing in 3 National Championship games while winning an NCAA Championship in 2008 before graduating in 2009. Benn was drafted by the Phoenix Coyotes but signed with the San Jose Sharks upon graduation from BC. Benn played 100+ NHLgames along with stints in the AHL and the Austrian Elite League before retiring in 2015. Until this year, Benn was the only NHL player in history to score a game winning overtime goal in the playoffs on his birthday.