Leland earned All-League honors in 1962 and All-CIF (California Interscholastic Federation, Los Angeles) in 1963 at Beverly Hills High School. An inspiring swimmer, he was a CIF finalist in 1961 and 1963. He earned six varsity letters in swimming and water polo at Cal, served as team captain of the swim team, and was a PAC-8 place winner in the 200-yard Butterfly and 1650-yard Freestyle. While player-coach of the Harvard Water Polo Club, Leland was a finalist in the New England AAU Championships in three events and the MVP. He finished second and third is his two appearances in the La Jolla Cove Swim, the most prestigious rough water swim in the United States. In 1964, Leland was named to the Sporting News annual list of the 100 most powerful people in the sports industry.