When I think of really good teams that just couldn’t win in the play-offs, the Washington Caps of the ’80’s come to mind. They had some great teams, and finished very high in the standings many years. I think they actually were tops in the league once or twice. They had some great players – Rod Langway, Denis Maruk, Mike Gartner – but they always found a way to lose.
Granted they bumped into some other great teams in those years – the Isles and the Oilers really owned the 80’s but for a team that was pretty solid, they ended up with not much to show for it.