Bender’s interest in baseball began at a very young age. His father., August J. (Gus) Bender, was a member of the Municipal Athletic Baseball Association, and managed some of Sheldon’s early teams. Bender was an All-Star infielder at Roosevelt High School and played amateur baseball for the Zephyrs, Kriegshausers, and Gebken-Benz teams in the Muny Leagues.

In 1938, Bender began playing professionally in the St. Louis Cardinals organization. What promised to be a brilliant career was interrupted by four years of military service. At the amateur level, he is remembered as a pitcher/shortstop, who played for Gebken-Benz, playing out of Carondelet, and winning the City Championship. After World War II, where he played Navy baseball at Treasure Island, California, the “Chief” spent 19 years with the Cardinals organization as a player, manager, scout, business manager, and Farm System Director. His interest in amateur baseball was always prevalent, as he moved to the Cincinnati Reds where he served as Vice President of Player Personnel.