Who was the greatest coach in Derby High School History? Many people feel that that Leo F. "Nuggy" Ryan, the man pictured, above deserves the title because of his accomplishments in coaching all three major sports at Derby High School at the same time. A graduate of Derby High School where he was also captain of the football team, he graduated from the Catholic University of America where he also played football  in 1925 and returned to Derby as a teacher and coach later that year. He became head football coach in 1926 and head basketball coach in 1931. His football teams won state championships in 1937 and 1940, and the 1937 team was even invited to play in a post season game in Florida. He won Housatonic League championships in 1928, 1932, 1936, 1937, 1940 and 1946.

His basketball teams were outstanding - especially the "Moxie Gang" in 1938 which played in the state's Class "A" tournament and made it to the semi-finals before losing to a Manchester team that went on to win both the state and New England championships.

Ryan Memorial

This memorial stone and flagpole in the Ryan Athletic Complex, formerly known as Coon Hollow Par, was dedicated to Coach Ryan on June 18, 1959 prior to the high school graduation the same night. Among those on hand for the dedication were two legendary high school coaches who were long time rivals of Ryan - Ed Finn of Shelton and Charles "Boots" Jarvis of Ansonia.

In 2019 when the new Payden Fieldhouse was built with the adjoining baseball/softball and football/track facilities replaced the earlier complex, the Ryan Memorial was moved to a new place of honor at the entrance to the complex.