Both sides need to compromise, not just the player. Nylander wouldn't just sit out, he can go play in Europe for 2 seasons and IIRC he can become a UFA. Another thing he could do is **** the Leafs and sign a 2 year offer sheet that doesn't give the compensation he's worth, where year 2 has a jacked up AAV forcing the Leafs to either lose him for less than he's worth, or match and deal and in two years have to choose to not qualify him at the end of the contract, or give him a large QO that he could accept. So. let's not pretend like he has no chips to play.
I'm willing to guess that most Leafs fans would be unhappy with Nylander being moved for a 1st, 2nd and 3rd if it were from a playoff team. Just imagine him signing an offer sheet with Nashville for 2 years, 7.5 AAV (year 1 being 6 million and year 2 being 9 million).
1. Nylander wouldn't be a UFA.
2. Nylander would lose more money going to Europe to play for 2 years than he would taking a long term deal in the 6s over what he wants.
3. Nylander would never sign a 2-year contract, as that means he has no contract during a likely lockout.
4. Nashville doesn't have the draft picks to offer sheet.
5. Nashville would
barely have the room for Nylander at that price, and they have multiple RFAs (including Fiala, good luck with his negotiation if you pay Nylander 7.5m) and Pekka Rinne to sign next offseason.
6. While I guess he could take 1-year deals every year at his QO, that is a HUGE financial risk to take as a young player, and would probably result in him being traded to a pretty bad team, away from endorsements, friends, success, and the countless opportunities to grow his value and make extra money.
7. Why would a team sign him to a deal like that, when they could be stuck with a 9.9m QO? What team has the draft picks, the current cap space, and the future cap space to do that without negatively affecting their own team or ability to sign players?
Nylander has no leverage. He is getting horrible advice, and is either going to screw up his future, or at the very least, give up all the extra money he'll get out of this standoff, by doing the standoff (while still damaging his reputation).