The Saint John native began his career at the Kennebecasis Rowing Club and went on to become a champion at several levels during an outstanding career that exemplified dedication, hard work and ability. Racing in pairs and eights competitions, Winchester won three gold medals at the renowned Royal Canadian Henley Regatta, gold, silver and bronze medals internationally and was a spare on the Canadian team for the Sydney Olympics in 2000. He also demonstrated a strong mental and physical toughness in an extremely demanding sport. Following back surgery in the late 1990s that would have ended the careers of many athletes, he staged a gritty comeback and won gold in the men’s lightweight pairs at the 2000 World Rowing Championships - the first time a North American crew had won the world title.Truly an outstanding career on the national and international stage. Inducted into the New Brunswick Sports Hall of Fame, May 31, 2008
Won 3 national titles while competing in the Royal Canadian Henley Regatta (1994, 1997, and 2000).
Bronze medalist at the 1996 and 1997 World Championships in the lightweight men's eight competition.
Silver medalist in the 1999 lightweight men's eight at the World Cup.
He was a spare on the Canadian team for the 2000 Sydney Olympics.
Won gold in the men's lightweight pairs at the 2000 World Rowing Championships.