Leon Draisaitl becomes the third fastest player in NHL history to 100 ...

It's more than four actually. Stastny didn't win a Cup, Federko didn't win a Cup, and Barry Pederson was only a depth player on that Cup-winning Pittsburgh team who didn't even play in the playoffs, so it's not like he had much impact that year either.

It's also getting harder and harder to win a Cup the bigger the league gets. The more players in the league, the lower the percentage of players who actually get to win a Cup. Add the Salary Cap, and it is not quite as easy to assemble great teams like the 80s Oilers, early 90s Penguins, or 90s / 00s Avalanche.

Pittsburgh is actually a good example of how hard it was to win even then. Jagr won two Cups as a young player, then never one the rest of the way, even though he became a much better player, and Lemieux was still around for a few runs as well. Meanwhile, Sakic and Forsberg got surrounded by a much better roster on a much richer team, and managed to win two Cups. You don't just need to assemble a great team, you also need to be in peak shape at just the right time, and have to hope that one of the other great teams around isn't in even better form than you are. See Colorado, Detroit and Dallas in the late 90s / early 00s. Or, alternatively, that a team who is a bad fit for you gets beaten by a team who is a better fit for you.

Ovechkin finally won a Cup at age 32, when some people thought he would never get one, and that's not because Washington wasn't good before or didn't perform well in other playoff runs. Take 2008/09, Pittsburgh won a seven game series against the Capitals in round 2, a series which featured three overtime games. Change the outcome just a tiny bit, and maybe it's Washington that wins that year, and people wonder whether Crosby and Malkin will ever win that Cup they so deserve. Sometimes the two best teams in the conference already meet in round 2, leaving the winner with a rather easy conference finale. Did the losing team have a bad run, just because they barely got beaten by the eventual champion? No. But people will still harp on about how they didn't make it out of the second round, completely removing all context.

Edmonton certainly hasn't managed to deliver a good enough team yet, but even if they did, it still doesn't guarantee anything, because there will always be other great teams around, and sometimes those teams will be better in a playoffs series, even if your stars are doing their job. For all the Cup-wins they got back then, Colorado and Detroit suffered even more losses at the hands of somewhat equally strong teams.