A three-sport athlete in football, basketball and baseball. He was captain of both the baseball and football teams, and he won the gold football award for being a member of the conference champs in football. Winstead was a teacher, coach and athletic director for more than 33 years. His coaching career record through 1989 in the sports of baseball, football and basketball was 579-372-5. Winstead was named Coach of the Year by the Quincy Herald-Whig in 1963.