Robert Madden was a three-year letterwinner in football and three-year letterwinner in baseball at the Academy. As a senior, he received the 1959 Adm. Giles C. Stedman Award while captaining the baseball and football squads. In baseball, Madden was named a Knickerbocker Conference All-Star three times (1955, 57, 58) while setting the Academy home run record. In football, Madden was a co-captain of the 1958 team which turned in a winning record after three straight losing seasons. He also received the Esprit de Corps Trophy for baseball as a senior which is awarded to the member of each athletic team who best embodies the spirit, drive and symbolism of his particular sport.