 A well-traveled player, he played for such teams as the Appalachian League's Bristol Tigers (1988), the South Atlantic League's Fayetteville Generals (1988–89), the Pioneer League's Salt Lake City Trappers (1991), the Florida State League's Charlotte Rangers (1992), the Texas League's Tulsa Drillers (1993), The Saint Paul Saints of the Northern League (1994 & 1998) and the Eastern League's Canton–Akron Indians (1995).Castillo began his managerial career with the Duluth–Superior Dukes in the Northern League in 2000, where he took the team from the league's worst record in 1999 to the Central Division Championship.For that feat he was named Independent Baseball Manager of the Year by "Baseball America".