I'm gonna be 1 of 100s of armchair GMs doing their best at a Tkachuk trade, so here goes nothing.
We all now know that Tkachuk wants out of CGY, and listed teams all with 0 state tax as well as hometown STL as teams with interest. I think it makes all the sense in the world to bring Tkachuk in the fold here. Another tid bit of info STL fans are forgetting is that Tarasenko still wants out of St Louis. According to Frank Seravalli he is not planning to rescind his trade request; with 1 year left he may be on his way out as well. So I think a plausible way Tkachuk gets out of CGY is through a 4 way trade with St Louis, New York and Arizona.
Full Trade:
STL - RFA Rights to Matthew Tkachuk & Jusso Valimaki
NYI - Vladimir Tarasenko (50% Retained) & Marco Scandella
CGY - Anthony Beauvillier, Zachary Bolduc, STL & NYI 2023 1st Round Draft Picks
ARZ - STL & NYI 2025 3rd Round Draft Picks ($3,750,000 Retained on Tarasenko)
Why this works for St Louis: STL gets their guy in Tkachuk, even though they have to part ways with Tarasenko, as well as defender Marco Scandella. Learn from the Flames it's not fun to lose your star players all in 1 offseason. St Louis gives up Bolduc, a 1st and a 3rd as well in this deal, which is fair value considering they do acquire Valimaki as well
Why this works for New York: Isles were rumoured to be in on Tarasenko from the moment he requested a trade and here it is. He had a poor 2020/21 campaign and had a stellar year this year. On the final year of his deal at 50% retained, he'll slot in with NYI perfectly. Isles also take on Scandella, to potentially replace Beavillier, Chara & Greene with Tarasenko, Romanov & Scandella would be a stellar offseason for Long Island, getting them back in the playoff hunt. To make cap work, would likely have to move Varlamov depending on Romanov's deal.
Why this works for Calgary. After losing Tkachuk & Gaudreau at least you can say you have 1 top 6 guy to show for it in Beauvillier. He unfortunately has been playing himself out of NYI and with his cap hit was deemed expendable. CGY also gets Bolduc in this deal, never hurts to have plenty of center prospects. 2 firsts from NY and STL each also very much helps. CGY essentially gets 3 1sts out of this deal considering Bolduc is a quite recent 1st round selection in addition to Beauvillier. CGY finally passes up on Valimaki who has not been playing his best hockey as of late.
As for Tkachuk's deal as he still is unsigned. I think you mutually agree to a 1 year deal THEN sign an 8 year extension during the season. If he's going back to his hometown team, you'd think Tkachuk would rather stay for 9 years and make more money rather than 7. I think it's fair to sign him up to a 1 x 7,000,000 extension (which is a direct extension from his current salary) then during the year offer him somewhere in the 9-10 range over 8 years. With Tkachuk also taking 7 mil this gives this team an "all in" feel as Kyrou, Thomas, O'Reilly and now Tkachuk all have contracts expiring. With Thomas already resigned, Tkachuk will be on his way to resigning, leaves O'Reilly & Kyrou as question marks. O'Reilly as captain could very well take a Pavelski or Giroux type deal and take a discount, and Kyrou will probably want just short of Thomas, so maybe around the 7 range. Also St Louis can sneak in and sign veteran Kessel on a 1 year deal.
You would have to think Vegas is offering a better package if they want him.
NYR and NJ do want him and they are probably offering better packages, and even though he might not sign long-term with them they can still acquire him and Calgary will trade him to the team with the best offer.
I actually think this could work if there were more pieces added to it. (for the Calgary-St. Louis side)
Also, we don't need another defenseman. We really could use a 3rd line winger imo