Kevin was a third baseman for 21 years at Cottleville & Harvester in the Eastern Missouri Baseball Association and played on teams that won the EMBA Little World Series. He is an active member of the C&H Athletic Association and has coached C&H American Legion teams.

Prior to that, Schaefer played for Francis Howell High School and was selected to the All-Conference team three years in a row. Kevin was inducted into the Francis Howell Hall of Fame in 2004 and then the St. Charles County Amateur Sports Hall of Fame in 2010.