Benn is a Top Gun alumni who played prep school hockey at Governor’s Academy where he won the John Carleton Award. He then went on to be a Division 1 scholarship hockey player at Boston College, where he played in 3 National Championship games, winning an NCAA Championship in 2008. Benn signed with the San Jose Sharks after graduating. He played 100+ NHL games along with stints in the AHL and the Austrian Elite League before retiring in 2015.