the toughest trophy to win in sports
But year after year, 15 captains of 15 teams fail in their pursuit of such a lucrative prize. The Stanley Cup is without a doubt the hardest championship trophy to win in all of professional sports. Harder than winning the Superbowl, harder the winning the World Series, and harder than winning the NBA Title. There are 16 teams in playoff contention, only other sport that can claim the same would be the NBA.