Which Toronto maple leaf has the most rings?

As of my last update in October 2023, the Toronto Maple Leafs player with the most Stanley Cup rings is Bill Barilko, who won four championships with the team in the early 1950s. However, it's worth noting that he is often remembered more for his tragic story than his accolades, as he passed away in a plane crash shortly after winning his last Cup. The Maple Leafs have not won a Cup since 1967, making Barilko's achievements particularly significant in the franchise's history.