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Mickolio was drafted by the Seattle Mariners in the 18th round of the 2006 MLB Draft. On February 8, 2008, he was traded by the Mariners along with George Sherrill, Chris Tillman, Adam Jones and Tony Butler to the Baltimore Orioles for Érik Bédard. The Orioles called him up to the Majors for the first time on August 20, 2008, and he made his debut that day.