While playing at Stillwater High School, Holliday played baseball and football. He was a highly touted quarterback who established an Oklahoma state record with 35 touchdown passes during his junior year. As a senior, Holliday earned All-American honors and his region’s Gatorade Player of the Year award in both sports.
Holliday eventually chose to play baseball professionally and was drafted by the Colorado Rockies in the seventh round of the 1998 Major League Baseball draft.
That would be the start of a 15-year MLB playing career, including six years with the Rockies. He finished fifth in the National League Rookie of the Year voting in 2004 and second in the Most Valuable Player voting in 2007 when he hit .