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Castillo began his professional career in 2006, playing for the AZL Cubs (seven games) and Boise Hawks (three games), hitting .188. In 2007, he hit .271 with 11 home runs and 44 RBI for the Peoria Chiefs. He split 2008 between the Daytona Cubs (33 games), Tennessee Smokies (57 games) and Iowa Cubs (one game), hitting .287 with four home runs in 91 games. With the Smokies again in 2009, Castillo's average dropped to .232, however he hit 11 home runs and drove in 32 runs.