Jackson attended a University of Minnesota and Western Nebraska Community College before existence selected per Seattle Supersonics with the Twenty-third pick in the 1997 NBA Draft. He was traded to the Denver Nuggets prior to his rookie year inside which he played 68 games prior to moving in to the supplementary familiar place in Minnesotthe in which he donned a Timberwolves jersey for two seasons. He experienced his better years inside Sacramento in which he played for the Kings from 2000 to 2005. The previous Sixth Man Award winner, Jackson suffered an injury early in the 2004-05 season that forced him to miss 51 games.