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Cherry pitched for the University of Oklahoma from 2000-2002. He was used mostly in relief his first season, but was a full-time starter by the time he finished at school. He had an overall record of 18-16 in 208 innings pitched.
The Philadelphia Phillies chose Cherry in the 10th round of the June 2001 entry draft, but he didn't sign at the time. The Chicago Cubs made him a 14th round pick the following year, and he signed with them.
He was a starter his first three minor league seasons (2003-2005). Cherry's 2005 season ended after only three appearances for the West Tenn Diamond Jaxx of the Double-A Southern League, after which he had Tommy John surgery.
When he returned to West Tenn in 2006, Cherry became a full-time reliever. He had a middle finger injury to his pitching hand in mid-July which also required surgery.
Cherry made his major league debut on April 23, 2007 with the Cubs against the Milwaukee Brewers in a relief appearance. He wound up being the loser in his MLB debut, but got his first big league win May 1 against the Pittsburgh Pirates.