Playing a style that suits you doesn't guarantee you a cup. It's just better than playing a style that doesn't. And while Keefe's system was better and more suited to his team, he quite frankly didn't always stick to it the best in the playoffs. Far too often we let the opponent dictate the style, and we'd try to match their style instead of committing to ours. Instead of pushing the pace, attacking offensively, and trying to control the game like a Colorado, we'd often get too comfortable playing a "safer", slower, lower event, more dump/grind-heavy game, and while we often outperformed the opposition in their style, it still made each goal more consequential and we'd end up losing by one goal on the goalie battle. Now we're tripling down on the parts of our past that worked the least for us.
There are no " inmates running the asylum". Building the best team means striking a balance between the present and future, much like we did. You need to give yourself the best chance you can when you have a great team, without fully depleting internal development. We traded some picks in our best years, but we also got some picks back, drafted well with the picks we had, and supplemented well with undrafted free agents.