No NHL franchise was won more Stanley Cups than Les Habitants. Montreal's 23 championships puts them 10 ahead of the second place Toronto Maple Leafs (who haven't won a Cup since 1967). Numerous legendary players have suited up for the Habs and they certainly have one of the sharpest uniforms in all of sports. And although they surprisingly came close in 2021, they haven't won a title since 1993. Let's drop the puck and get started!