Coach Winters has spent 14 seasons as a Varsity Basketball Coach at Oregon, Rockford Jefferson, Rock Falls and Boylan Catholic in the state of Illinois. He is entering his first season at Harlem High School. His career record is 304-112 (.731 win percentage). He has never had a losing season as a head coach and led three different programs to the State Tournament (SuperSectional or beyond). Rockford Jefferson placed 4th in the state in 2005. Rock Falls made a SuperSectional appearance in 2006 as the smallest AA school in that class. Boylan was a SuperSectional qualifier in 2013 and 2016.
Coach Winters has been named the IBCA District Coach of the Year seven times and was the Sauk Valley Newspapers Coach of the Year in 2006 and the NIC-10 Coach of the Year in 2016. His teams won 7 conference titles, 7 regional titles and 4 sectional titles. He led his teams to eight 20-win seasons and two 30-win seasons.
Coach Winters has coached players who have gone on to play at Kansas State, New Orleans, Florida A & M, Evansville, Southeast Missouri, Ball State, Wisconsin-Green Bay, University of Illinois-Chicago, Wisconsin-Milwaukee and Air Force and many others who have competed at the Division II, Division III and JUCO levels.