Holliday was originally drafted by the Colorado Rockies in the seventh round of the 1998 Major League Baseball Draft.
After spending most of the off-season on the trading block with the Rockies, Holliday found himself most of his Spring with the Athletics. After the Athletics failed to get off to a strong start, it was unlikely the Athletics would have been able to resign him as a free agent after the 2009 season.
Holliday was recruited out of Stillwater High School, in Oklahoma to play quarterback at Oklahoma State, but he chose to sign with the Colorado Rockies and was signed by scout Pat Daugherty.