Growing up in Highwood, Illinois, Leo participated four years in football at Highland Park High School and was an All-Suburban selection.
Entering Lake Forest in the fall of 1949, Leo was a stand-out member of the football team. As a freshman, he was Honorable Mention All-Conference. His sophomore year, he was a first-team All-Conference selection at the fullback position. Due to an injury, Leo was unable to compete his junior season; however, he returned to the field at full strength senior year as he captured the Clayton Mark Most Valuable Player trophy on the conference championship team. Leo was also a member of the Kappa Sigma fraternity.
Following graduation, Leo embarked on a 30 year career in the auto business and was an avid golfer.