Mr. Wingo is a Cleveland native graduating from John Adams High School with a Bachelor’s Degree from Cleveland State University in Urban Studies and Business Management. He has two Masters of Education Degrees in School Counseling and Supervision and Administration from Brooklyn College.

Mr. Wingo has worked in the field of education for over forty years. He started in Cleveland working for Jim Brown's Black Economic Union as a college counselor and The Kinsman Opportunity Center working with high school students during the summer. He has worked as a substitute teacher in Atlanta, Georgia. As a school counselor in the New York public school system as well as an Assistant Principal and Central Office Administrator. He also worked as a counselor at The Boys Choir of Harlem and a member of Harlem’s Community Board #10.

Returning to Cleveland he worked as Cleveland Municipal School District as Executive Director of Children and Family Services, Family and Community Engagement Office and the Districts Ombudsman. While working for the District he was the Representative for the Fatherhood Initiative Program and has participated since 2004.