If you win, whatever you did/do is good enough. If you lose, whatever you did/do wasn't good enough. It's that boring and simple. If you win the Cup, anything you did must've been at least ok, because you won, and wouldn't have won otherwise. It's ok that one of your top defenseman was a waiver wire pick up. You can't count on something that ridiculous to happen, but it did happen, so it's all just part of building a team. But 5 years before a Cup run, if you say "oh, we'll just get one of our best players on waivers, don't worry about it", fans would go apeshit, because that's not how you properly build a team.
Objectively, if you give a 30+ year old $10m, especially a goalie, that's a bad move. It's still a bad move, even though Florida won. Because so many things had to go their way for that to have happened after they gave that contract to him. If Tkachuk wants to stay in Calgary, they're not taking Huberdeau nearing 30 with a year left on his deal. That trade simply does not happen. However, Tkachuk wants out, at the same time as Huberdeau has a 100+pt season, and both sides get to make that work. If either variable doesn't exist, if Tkachuk is fine in Calgary, and/or Huberdeau has his career average of 75pts or so, it's not a deal that happens. Calgary wouldn't be that stupid. But they were forced into it, and could justify it in some way. Then the terrible contract they give to Huberdeau, that's all on the Flames. They didn't have to do that.
The Panthers won, so anything they did before June 2024 is no longer up for debate. If they don't win again this year, then questoions can start again. And they just keep adding on the more years they go without winning.