 Maldonado originally signed with the Seattle Mariners organization in as a non-drafted free agent.He was traded to the Houston Astros for infielder Carlos Hernández on March 21, 2000, then spent time in the minor league systems of the Astros, Chicago White Sox, and Pittsburgh Pirates, before making his major league debut with the Pirates in .Maldonado appeared in eight games that year, collecting two hits in nineteen at-bats, for a batting average of .105.