I agree with what you said EB but the problem is that you're always using baseball moves as a comparison, which confuses other posters and hurts the point your trying to make. I'll use the moves the Maple Leafs made in the past which led them to what they are today: one of the best teams in hockey.
First when new management took over they gave away Phil Kessel and Dion Phaneuf because of their big long-term contracts. Similar to a degree to Shea Weber and Carey Price's tremendously big and long contracts. Weber and Price's contracts are gigantic compared to Kessel and Phaneuf's, but the point i'm trying to make is that Kessel and Phaneuf's were the two biggest contracts on the Leafs at the time, just like Weber and Price's are at the current time on the Habs team.
Contracts such as these are salary cap killers and hurt the team since money that could be used to fill up roster spots with quality players is used up to pay those big long-term contracts. There are exceptions, of course. Pittsburgh wouldn't be who they are without Sidney Crosby and Evgeny Malkin and the Capitals wouldn't be who they are without Alex Ovechkin. Same thing with the Oilers and young Connor McDavid.
But Toronto didn't see a future with the likes of Kessel and Phaneuf's contracts eating up a large portion of its salary cap for years to come. That's why they literally gave them away in order to clear up cap space and start building for the future. Getting rid of their two superstars also made the team considerably weaker which would be good in the long run since it would put them near the bottom of the standings. Remember that first season after Kessel and Phaneuf were gone? They could barely score any goals! The top scorer on the team was P.A. Parenteau, whose contract was still being paid by the Habs at the time. They sucked!!! Goalie Jonathan Bernier was a sieve and the defence wasn't very good either. It led them to finish near the bottom of the standings and it eventually led to them drafting the likes of Mitchell Marner and then Auston Matthews. They had previously drafted William Nylander.
But all of this never would have become possible unless they unloaded the big contracts of Kessel and Phaneuf which permitted them to finish at the bottom of the standings, clear up some much-needed cap space and start all over. They already had a foundation of promising young players to build around: James Van Riemsdyk, Morgan Rielly, Jake Gardner and Nazem Kadri. William Nylander had just been drafted and if the team hopefully ended up at the bottom of the standings it would give them the opportunity to draft some top 5 talent, which they did in Marner and Matthews. And with all the cap money now available to them they were able to sign a promising young goalie in Frederik Andersen. What did they do with the money they had left? They re-signed young promising players such as Kadri, Gardiner and Rielly to team-friendly longterm contracts. It also allowed them to lure several very promising European free agents and last year they re-signed Nikita Zaitsev to a longterm deal.
But that's what an organization has to do to become a contender: be willing to make the sacrifice. But seeing how habs fans and the local media have reacted to the recent Habs mini-streak has only shown me that they will never accept a full rebuild like many of today's contending teams have went through over the years. So for the next few years it'll be the same story again and again: lack of scoring, poor defence, an aging injury-prone highly-paid superstar goalie with 8 more years left to go on his contract and an aging solid defenceman on the blue line with a huge long-term contract which will last until 2026.
When the team will continue to struggle fans and media will demand changes and once again the coach and likely the general manager will be axed. That coach will get replaced by another french-speaking head coach and it wouldn't surprise me if that coach has coached the Habs in the past. And then the fans and media will call for a full rebuild like other successful teams have done in the past. And as soon as the Habs' slump comes to an end all will be good and forgotten again...and again...and again.