The Columbus Crew drafted Wingert in the second round (twelfth overall) in the 2004 MLS SuperDraft. Despite his collegiate success, MLS teams were skeptical about his ability to adapt to the faster and more physical professional game. Nevertheless, Wingert managed to earn a spot on a very good Crew team and was a versatile member of the squad for two years. While in Columbus, he played as both a defender and a defensive midfielder. On January 20, 2006, the Crew traded Wingert to Colorado Rapids for a fourth-round pick in the 2007 MLS SuperDraft.