A few things to note about that table...
- Dominik Hasek did not win a Cup with his original team. He won his first Cup with Detroit in what would be his third city (Chicago and Buffalo being the first two), then won his second Cup after leaving for Ottawa and returning to Detroit. His experience is instructive, and we'll get to that.
- Eddie Shore won his last Cup at the age of 36 in what would be his last year with the Boston Bruins. He was not in the prime of his career by this time, and this Cup win came ten years after his previous success.
- Jean Beliveau won 10 Stanley Cups for a bona fide dynasty, winning his ten Cups in the space of 16 seasons. These days, winning four in 11 years is as close to a dynasty as we seem to be able to get.
Hasek, it is worth noting, won neither of his Hart Trophies with the team he backstopped to a Stanley Cup. He won both trophies with the Buffalo Sabres, and in neither year in which he won the Hart did his team win more than two rounds of the playoffs. In Detroit, a team was -- in fact had already been -- built around him. Caps front office, take note.
History seems to confirm what folks suspect -- hockey is a young man's game. There seems to be, even for the best of the best, a narrow window in which to win the biggest trophy of all (at least playing for the team with which they started their career). Of those multiple Hart Trophy winners, the last player to win a Stanley Cup with the team that drafted him was Mario Lemieux, in 1992 at the age of 26.
This isn't intended to be the voice of doom with respect to the Capitals' chances of ever winning a Cup. In fact, we like their chances to do it soon (as long as the front office does their job). But Ovechkin will be 25 at the end of next year -- approaching middle age on the table displayed above -- and there might be only so many "next years" in which to do it.