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Haigwood was originally selected by the Chicago White Sox in the 16th round of the 2002 Major League Baseball Draft. That season he was named the Arizona League All-Star left-handed pitcher after going 8-4 with 74 strikeouts and a 2.28 Earned run average in 14 starts for the White Sox rookie league team. Before the 2006 season, he was traded by Chicago along Gio Gonzalez and Aaron Rowand to the Philadelphia Phillies in the same transaction that brought Jim Thome to the White Sox. Then, during the midseason was sent by Philadelphia to the Texas Rangers in exchange for Fabio Castro. He had a combined 3-7 with a 3.58 ERA in 27 starts for Double-A Reading Phillies and Frisco RoughRiders.
In a four-season minor league career, Haigwood has posted a 35-18 record with 475 strikeouts and a 3.58 ERA in 88 starts.
In April 2007, the Boston Red Sox acquired Haigwood from Texas for a minor leaguer and cash considerations. He was assigned to the Portland Sea Dogs. Haigwood became a free agent at the end of the 2008 season and signed with the Pittsburgh Pirates. In April 2009 he was given his outright release from the Pirates and later signed with the Winnipeg Goldeneyes of the Independent League. On June 23, 2009 Haigwood Signed A Minor league contract With The A's.