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Jackson played in the Major Leagues for 21 seasons, from 1986 to 2006. He played for five different teams during his career, including the Kansas City Royals, Chicago White Sox, Baltimore Orioles, Arizona Diamondbacks, and Atlanta Braves. Jackson was a six-time All-Star and won the Gold Glove Award eight times. He also won the Silver Slugger Award twice and the American League MVP Award in 1993.