Joined: Sep. 2020
Posts: 3,338
Likes: 1,900
Caps and Leafs fans on this site (and really every fan tbh) can't ever parse out the very different realities of what a player is actually "worth," how a generic NHL GM values certain roles, and what specific teams will do versus what they should do.
Objectively by any WAR-type stat Nylander is "worth" a whole lot, probably the amount of futures being offered here if not more. I don't really think any fan of any team would dispute that. The problem for the Leafs is that correctly or not, NHL GMs do not value scoring wingers in the last year of their deals that are about to get paid big money quite as highly. This is incredibly obvious from recent trades -- Fiala, DeBrincat (twice), Meier, Bertuzzi, Stone, even some centers like PLD and Eichel. The only player traded recently to get the type of return they are actually close to being "worth" is Tkachuk, an MVP caliber player on a different playing field than all the ones I just listed. NHL GM's probably are also very put off by what has been reported so far as Nylander's (justifiably) massive contract demands.
Finally, there are the team-specific things. Leafs fans need to understand that no matter what he "should" do, BMac has made it abundantly clear through media channels that he is not trading Wilson even for an upgrade in the form of Nylander. Obviously I do not follow Toronto media or rumors as closely, but I assume that the Leafs would like to get back some form of top NHL talent back in a Nylander deal and Caps fans need to understand that as well.
For all of these reasons, I don't really see any trade scenario that makes sense for both teams around Nylander (or Wilson for that matter), especially this one that doesn't really solve anyone's problems.