 He started his career at A.S. Roma but never represented the team officially, being loaned to amateurs Calcio Lecco 1912 and Teramo Calcio for the duration of his contract.In summer 2003, Serie B side U.S. Città di Palermo signed Pepe in a co-ownership deal, for a nominal fee of just €500, and he scored one goal in 19 appearances to help his team gain promotion to Serie A for the first time ever, as champions.Pepe was loaned to Piacenza Calcio also in the second level in July 2004, in order to gain experience.