For nearly five decades, Jess was the manager of the Cape Girardeau Capahas semi-pro team. His tenure there began in 1967 and he served as a player-manager for 37 years. Bolen was named Man of the Year by the Cape Jaycees in 1970.

In 1992, Jess was elected to the Southeast Missouri Baseball Hall of Fame. In 2007, Jess was named Sportsmanship Manager of the Year by the National Baseball Congress. The next year, he was inducted into the NBC Hall of Fame and in 2010, Bolen received the ultimate tribute when he entered the Missouri Sports Hall of Fame.