Though Jackson committed to play 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.
He made his major league debut on April 5, 2010 against the Kansas City Royals, going one for five. He hit his first major league home run on April 25, 2010, off of Colby Lewis of the Texas Rangers. Through the first month of the season Jackson led the majors in hits with 36, and was named the AL Rookie of the Month.
On June 2, 2010, against the Cleveland Indians, Jackson made an outstanding catch in the ninth inning of Armando Galarraga's near-perfect game. The perfect game was later ended with two outs in the ninth after a blown call by umpire Jim Joyce.
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