Born in 1943, Winston began coaching in the 1980s at the AA and AAA levels in Winnipeg South. His coaching career eventually led him to become a member of the Board of Directors of the Winnipeg South Minor Baseball Association. His volunteer efforts expanded to include serving as the Vice-President of Policy on the Baseball Manitoba Management Committee, as well as serving on Baseball Canada’s Bylaws Committee. His involvement led him to the Pan-Am Games in 1999 as a member of the Technical Committee. He was also a representative for the Western Canada Baseball Association at numerous championships, including the 2011 Bantam AAA championship.