The problem is guaranteeing that. How do you know you are getting a package that makes the team better? It's a crap shoot at best and as I mentioned, history does not bode well for the teams jettisoning star players.
It is easy to sit here and prophesize about how much better the team would be but reality is a completely different thing.
Random example, does Dylan Guenther and an unprotected first make this team better now and in the long term? That's the type of uncertain return you would get for Tkachuk. Might be good, might absolutely slam the door on us being a cup contender in the next 5 years. Roll the dice and find out, or just stick with the best player in the deal.
This is a completely valid point regarding the uncertainty of whether what we'd get would take us to the next level.
I'm fine to keep Tkachuk and try to give Green a chance to help him develop into the leader we need, but I'm also fine to move on because as much Tkachuk is a unicorn, high scoring, hitting, and penalty taking winger who is really bad in his own zone isn't the mould of player I think can help us have long term success. Especially when that type of player was made captain in less than ideal circumstances and now you're kinda stuck with him as C of a team that was poorly constructed/not set up to help him succeed as a leader.
In a hypothetical trade, I'd want the right fit of guys coming back (cost controlled, similar output, etc. that other GMs are willing to give up because they think Tkachuk can push them over the edge). Guenther wouldn't be that for me but someone like Keller, Lafreniere, etc., along with something like an unprotected first which we could definitely considering how asset depleted we are.
I'm not actively pushing for it, and am cheering for him every night as long as he's a Sen, but if management decides they want their core to look another way, I'm open to it.
