Holiday attended Roosevelt High School in San Antonio, TX. In football, he was named as the top high school scrambling quarterback in the nation. After a heavy bid from Nebraska, he eventually committed to the University of Notre Dame. Holiday was the starting quarterback for three years at the university, leading them to the Gator Bowl in his final full season at Quarterback. During that time, he broke the school's rushing record for 100 yard games in a season by a quarterback as well as most completions without an interception and touchdown passes in a game, the latter two which were broken by Brady Quinn. During his senior year at Notre Dame, Holiday was converted to a Wide Receiver and Punt Returner, due to the emergence of true freshman Quarterback Brady Quinn. Even though Holiday never played college baseball, he was drafted by the Cincinnati Reds in the 44th round of the MLB amateur draft in 2002.