Olin Stratton began his career as a teacher and Principal in Shipman, IL after receiving degrees from Southern Illinois University Carbondale and the University of Illinois and serving in the U.S. Army AirCorp during World War II. In 1947, Mr. Stratton became part of the Highland Community Schools, serving first as teacher, then coach, high school principal and finally as Superintendent from 1958 to 1985. While Mr. Stratton was Superintendent, later he became the President of the Illinois Association of School Administrators. He was elected to the Board of Directors and also served as President of the American Association of School Administrators (AASA), a world-wide organization of 20,000 members

In 1989, Mr. Stratton became Mayor of Highland. As Mayor, he initiated a Weinheimer Community Center expansion and numerous Beautification Awards prior to his death in 1990. He was a Charter Member and Past President of the Highland Optimist Club. As president, he started the Optimist Basketball League at the Weinheimer Community Center. Olin was a member of Highland Veterans of Foreign Wars (V.F.W.) Post #5694, the American Legion Post, the Highland Historical Society, the Highland Masonic Lodge, and Associated of Retired Teachers. He was a Past President of the Highland Chamber of Commerce and Past Chairman of the Weinheimer Community Center Board. Mr. Stratton also served as Chairman of the U.S. Bicentennial in 1976.

Olin was the assistant to head basketball coach Ed Hilbert, helping two teams go to the Illinois State Basketball Tournament in 1953 and 1958. He was also instrumental in the building of the new Highland High School in 1976 through his service on the Governor's Task Force for Education in developing the concept of the Capital Development grants. Because the Highland School System was recognized as one of the finest school systems in the state of Illinois and in the nation, Mr. Stratton was presented the annual Distinguished Service Award by Southern Illinois University Edwardsville.