Question: what canadian has won the most olympic medals?
Answer: Olympians. The Canadian with the most times at the Winter Olympics is Jasey-Jay Anderson, who appeared at 6 Olympics; 1998, 2002, 2006, 2010, 2014, 2018. The Canadian with the most Winter medals is Cindy Klassen, who has 6 medals; 1 gold, 3 silver, 2 bronze.