In 1999, Baseball America named Jackson the best 12-year-old baseball player in the nation, and the best 15-year-old baseball player three years later.

Jackson attended Billy Ryan High School in Denton, Texas.

In basketball, he was listed as the #10-ranked high school point guard in the country by Athlon Sports after he averaged 22.5 points, five rebounds and three assists per game his junior year in high school. In baseball he hit .423 with five homers and 34 RBI for his class AAAA Texas State runner-up baseball team and was rated the No. 14 draft prospect among high school players in the nation by Baseball America.

Though Jackson committed to play both baseball and basketball for Georgia Tech, the New York Yankees drafted Jackson in the eighth round (259th overall) in the 2005 Major League Baseball draft. To convince him to sign instead of attending Georgia Tech, the Yankees offered Jackson $800,000, a record signing bonus for an eighth round pick.

From 2005 to 2009 Jackson rose up the Yankees organization and after a slow start, he became a top prospect for the Yankees. For the 2009 season he was the Yankees top prospect according to Baseball America.

After the 2009 season, Jackson was added to the 40-man roster to protect him from the Rule 5 draft.

On December 9, 2009 Jackson was traded to the Detroit Tigers as part of a three-team trade that brought Curtis Granderson to the Yankees. Jackson entered the 2010 season as the Tigers third-best prospect, according to Baseball America.

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Wikipedia