Kammala jumla mai zuwa: Rupp ya buga wasan hockey a makarantar sakandare a St. Edward High School a Lakewood, Ohio. An fara kirkirar shi a zagaye na farko, na tara gaba ɗaya, ta New York Islanders a cikin NHL Entry Draft na 1998. Bayan ya kasance ba a sanya hannu ba yayin da yake wasa a gasar Ontario Hockey League (OHL) tare da Erie Otters, duk da haka, Rupp ya zaɓi ya koma NHL Entry Draft kuma daga baya aka zaɓe shi a matsayin na 76 a cikin
2000 daga New Jersey Devils.