If you ask any NHL player what their ultimate desire is, the answer more often than not will come back as "To win the Stanley Cup." You won't hear many players going on about individual accolades or the pursuit of stacks of cash. Yes, those things are nice, but a career that ends with nothing to show for it, save some individual hardware and a healthy bank account, is a career unfulfilled.
We want our favorite players to win the Cup—we want them to experience the joy of lifting that chalice over their head and cry tears of joy. It's something special to see; if you don't believe it, watch the video of Joe Sakic passing Ray Bourque the 2001 Stanley Cup. That's true emotion. That's a career fulfilled.
Bourque was one of the lucky ones, a superstar that nearly went through his entire career without winning the Cup, but he was able to realize his dream in the final game of his final NHL season. Some very talented players won't be as lucky as Bourque.