In the late 1950s, a group of Cleveland citizens began working for a city high school. The first step was taken when a ninth grade was added to Arnold Junior High, now an elementary school. On May 12, 1965 voters passed a referendum that allowed for the issuing of $2 million in bonds for construction of the new high school. The new school was completed in 1966, and in September of that year a historic walk took place from Arnold to the new high school to start the first year of school at CHS. Every year during homecoming week, a parade is held on Raider Drive to commemorate the anniversary of this historic walk. Former principals include James Traylor, Jim Sharp, T.C. Henley, Charles Carrick, Maxine Hughes, Doug Greene, Ken Willey, and Chuck Rockholt.