Born in St. Louis, Missouri and drafted by his hometown Cardinals, Robinson first reached the big leagues with the Tampa Bay Devil Rays, who plucked him from the St. Louis organization in the second round of the November 1997 expansion draft.
The speedy left-handed outfielder appeared in two games for Tampa Bay in September 1998. Over the next two years he bounced from the Mariners’ organization (leading the Triple-A Pacific Coast League in triples in 1999 and finishing third in steals despite playing just 79 games), to the Reds, and finally to the Yankees’ farm system, spending the entire 2000 season at Triple-A Columbus.
After returning to the Cardinals as a minor-league free agent in December 2000, Robinson saw his first extended major-league action the following summer. Used mainly as a pinch-hitter and defensive replacement, he batted .285 with 11 steals and 34 runs scored in 114 games.