The Stanley Cup is the trophy awarded annually to the winner of the National Hockey League play-offs. "National" covers both the U.S. and Canada. "Hockey" means ice hockey here.
The Toronto Maple Leafs last won the Cup in 1967 and have shown no sign of repeating the feat during my twenty-five years in Canada. Nevertheless, loyal fans keep telling themselves, "Next year...."
The T-shirt on the left is misusing their logo to poke fun. The juxtaposition with the T-shirt on the right is icing on the cake.
Nikon Zf, 35mm f/1.8S