With football recruiting overtures from colleges and universities all over the country—including OSU—Holliday instead chose professional baseball after graduating high school. The Rockies selected him in the seventh round of the 1998 Major League Baseball draft as a third baseman. Widespread concerns that he would choose football over baseball prevented him from being drafted earlier since he had already committed to OSU on paper to play football. Thus, Rockies scouting director Pat Daugherty signed him for an above-slot $840,000, the most money paid to any player in that round.