Wow, Lanny_McDonald, you love to write novels. Unfortunately, your entire dissertation is presupposed on the assumption that Gaudreau would have been willing to sign sooner. Gaudreau was almost certainly advised by his agent not to sign once last season started, since that season would not have been expected to produce comparable numbers to previous years, and both Gaudreau and his agent would have been just as aware as you that their leverage to get the best possible deal would only increase with time.
You are assuming that the Flames didn't make a very good offer. There is absolutely no evidence on which to base that assumption. Also, Gaudreau may have told the Flames that he would not discuss contract extension with any potential trade partner, thus significantly reducing his trade value.
The emergence of Mangiapane has been a surprise to everyone. However, his scoring pace is likely unsustainable in the long term, as his shooting percentage is miles above his career average. This has created a problem for Treliving, because being unsure of what to expect from Mangiapane and having limited cap room, he signed the winger to a "show me" contract. Now Mangiapane will be overpaid in his next contract, and will likely underperform that contract. This will be an unpopular opinion, but Treliving might have to trade Mangiapane's rights at the draft so that some other team can overpay him. Pitlick, Zadorov, Brouwer's dead cap hit, and possibly Gudbrandson will be gone, replaced by players mostly on entry-level deals. That will leave enough room for Treliving to extend both Gaudreau and Tkachuk. I suspect he will offer them both 8 year deals, to keep the AAV a bit lower in Gaudreau's case, and because that's one thing they won't be able to get on the open market. He should still have enough to offer a contract with term to Kylington. I do believe that Kylington is legit, and a I think a long-term deal would be preferable over a bridge in his case.
Of course, Mangiapane will have to be replaced with someone who can score. Hopefully one of the youngsters will be ready to fill that role next season.
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