It definitely did damage and the compounded the damage.
To me Johnny Hockey and Toews wouldn't be that different in value to the team... arguably even Kadri or Nuke. Gaudreau was the flashiest player on the team, but in terms of importance, he was behind Cheese and Lindholm quite easily. IMO you could make a case that Kadri or Toews are the 4th more important player on the team (I'd argue Toews ahead of Rants personally).
You could also point out Hamilton in Carolina too... he was their 2nd or 3rd best player that they let walk.
Now the Cheese situation... that was easily a situation forced by a GM feeling the heat to win immediately and ownership pressure. They did what they could to get the best pieces back and not rebuild. Probably the wrong way to handle it, but that blood needs to be shared... not just on one guy.
Overall though, Calgary was on a heater and number of places were predicting they were the Cup favorites. You'd be a madman to trade pending UFAs for assets in the midst of a contending year. I'd F riot if the Avs did that. Cups are hard to win and if you have a chance, you take it. Even if it fails it is better to try.
You're right, it's the same situation with Devon Toews and my feeling is the same as it always is in that type of situation. If the player doesn't want to sign long-term over the summer 1 year prior to being a free agent then why is he suddenly going to want to sign long-term 1 year later ?
Sometimes they do and it's because those players are usually entrenched within the organization and while they want to be paid fairly, there's no other place they'd truly rather play. (Landeskog, Stamkos)
Other than that, the 3 most glaring examples of players
saying all the right things in the media but not really wanting to stay where they were are Tavares, Stastny and Gaudreau. I'm quite certain all of those GMs were 'surprised' to see those players leave but that's the risk they decided to take by allowing those players to get to UFA.
I'm not suggesting that these are easy decisions but if you're in the business of looking out for the long-term health of an NHL franchise then it's up to the GM to set a deadline over the summer to get a deal done with the player and if you can't come to an agreement, you have to take the decision that you're either going to trade the player or keep him one more year
knowing that he's more than likely gone.
I don't agree with you that Calgary was close to being a contender 1 year before Johnny Hockey was set to be a UFA. The 2020-21 Calgary Flames finished with an under .500 record (26-27-3) in that shortened season during the pandemic and they missed the playoffs in the Canadian division of those weirdly configured conferences.
So at that point, you make the correct decisions as the GM and leader of the Calgary Flames that if Gaudreau doesn't want to re-sign, you move him out for the very best package that you can get. Sometimes taking a step backwards means you're going to be able to take a big step forward in the near future.
So to get back to Toews, if the Avs can't get him signed long-term this summer, then yes, I do hope they move him for the very best package they can get OR if they decide to keep him for his last year of his deal at $4.1M - then they HAVE TO BE ALL-IN this year and when I mean ALL-IN, I mean ALL f***ING IN, if you know what I mean.