He played for the Kansas City Royals, Cincinnati Reds, Chicago Cubs, Pittsburgh Pirates, Philadelphia Phillies, St. Louis Cardinals, and San Diego Padres.

His family moved to the greater Denver area, where Jackson starred in three sports at Aurora Central High School.

Trailing the Blue Jays three games to one and facing elimination, Jackson tossed a complete-game shutout and kept the Royals alive.

After disappointing seasons in 1986 and 1987, Jackson was traded along with Ángel Salazar to the Cincinnati Reds in exchange for Ted Power and Kurt Stillwell.

He tied for the National League lead in wins in 1988 with 23 and, Jackson combined with 18-game winner Tom Browning for the best pitching tandem in baseball that season.

In total, Jackson played in three World Series for three different franchises: the 1985 Kansas City Royals, the 1990 Cincinnati Reds, and the 1993 Philadelphia Phillies.