Cunningham was drafted by the Chicago White Sox in the sixth round of the 2005 Major League Baseball Draft. After two years in the White Sox's organization, he was traded to the Arizona Diamondbacks for Danny Richar on June 16, 2007. On December 14, 2007, he was acquired by the Oakland Athletics in the trade that sent Dan Haren to the Diamondbacks. He was called up from the minors for the first time on August 30, 2008.
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