Cy had a stellar all-around high school career in Minneapolis. He earned a football letter and a degree from the University of Minnesota in 1928. Cy came to Two Harbors in 1930 and taught history, political and natural science, and coached football, track, baseball, basketball, and was athletic director at various times. In his 23 year career, as Two Harbors basketball coach, his teams won six District Titles and were perennials in the Region 7 Tournament. His coaching peers chose him as president of the Minnesota State Coaches Association in 1949. Cy was elected mayor of Two Harbors four times. After leaving education, Cy became Administrative Assistant to Governor Orville Freeman and eventually State Insurance Commissioner.