Born on March 31, 1913, in Nashville, Tennessee, Bennett moved to Akron, Ohio, with his family when he was five years old. He played for the basketball team at East High School (now East Community Learning Center), lettering in three seasons and making it to the finals of the state championships. He also played football there on the team that pinned the last defeat on the Massillon Washington High School team coached by Paul Brown that went undefeated for 35 consecutive games over seasons.[2]
Playing for Westminster College in New Wilmington, Pennsylvania, Bennett racked up 1,168 points during his career, twice being named as an All-American and leading the nation in scoring in two seasons. He scored 21 points to lead Westminster to a 37–33 victory over St. John's University on December 29, 1934, in the opening game of the first collegiate doubleheader played at Madison Square Garden.[2][3] Leading all scorers with 11 points, Bennett led Westminster two days later to a 28–24 win over City College of New York, marking CCNY's first loss at home after 42 consecutive victories.[4]