attended the University of Missouri at Kansas City, earning a B. A. in Secondary Education and a Masters degree in Curriculum and Instruction. He taught Social Studies classes (primarily Government and Economics) at Van Horn High School in Independence, Missouri for just over twenty years, from January of 1985 through May of 2005.
Throughout his tenure at Van Horn, Winston was actively involved in professional development activities and school improvement initiatives (including a stint on the District Professional Development Committee).
He kept a journal of many of his ideas, along with critiques of current practices. Between 2001 and 2003 these writings were collected, augmented, and ultimately published in book form as "Edutopia: A Manifesto for the Reform of Public Education."
Since retiring from the classroom, Winston has remained actively involved in efforts to improve the quality of public education.