By 1990, Show had lost his regular spot in San Diego's rotation. The Padres did not pick up his option and bought out his contract for $250,000. Though Show had become known for his tardiness and confrontations with teammates and management in San Diego, the Oakland Athletics had taken risks on troubled players before. They signed Show as a free agent prior to the 1991 season. Show also played in 1990–91 with the Mayaguez Indians of the Puerto Rican Winter League.