He attended San Fernando Valley State College.

His best year in professional golf was 1983 when he teamed with John Cook to win at the World Cup.

His best finish was a T-2 at the 1994 NIKE Dakota Dunes Open.

After turning 50, Caldwell played on the Champions Tour from 2000 to 2006.

He lives in San Antonio, Texas with his wife, JoAnn.