He has an extensive background reporting on the game of baseball at every level. Overbey has been covering high school baseball for the St. Louis Post-Dispatch since 1991. He is the Associate Preps editor of the Post-Dispatch and covers high school and collegiate sports. He first began writing about high school baseball in 1982 with the St. Charles edition of the Post-Dispatch.

From 1982 to 1999, Overbey covered American Legion baseball for the Post-Dispatch, working the 1999 American Legion World Series in Alton. He followed Cottleville & Harvester to the Great Plains Regional in Ely, Minnesota.

Overbey has covered the NCAA College World Series in Omaha for the past sixteen years.

A member of the Baseball Writers Association of America, Overbey has written about Cardinal games for the Associated Press since 1998. He has worked seventeen World Series.

Overbey began his career in 1979 at KMOX Radio as a sports producer for Cardinal broadcasts with Jack Buck and Mike Shannon.