Matthews should really have been locked up when you signed Tavares, he ends up becoming more expensive than needed now. But it does sound like Matthews doesnt want to sign a team friendly contract, thats a problem when you are giving him a weapon like Tavares to play with
Saying Nylander isnt need right now is a bit insane, if you can get him on a team friendly contract I wouldnt trade him. Then i'd sign Kapanen to a low long term deal and trade him for a good D. Nylander is not finished growing, he is gonna be worth more when he finds his place in the team and start to deliver better. Give him a no-trade clause if he signs very team friendly long term if he is nervous about getting traded to some shitty place, because that might actually happen, I understand Nylander and Leaf fans should try to understand his position.
I also like Kapanens grit, so its a really nice position to be in for the leafs, and Kapanen is making this very uncomfortable for Nylander. I just still dont think Nylander will be able to give us a stud D via a trade, Nylander hasnt reached his final form yet, which is why it makes more sense to keep him unless a team will give a stud D. for his potential.