I know this is a couple days old and was just banter on a podcast. But I have to say trading 1st rounders is a bad idea. They've been traded, along with a bunch of other picks, and it hasn't helped. But I have another mindset with this.
I think the team is at a place where you need to consider two scenarios/options with those picks. You either re-sign Matthews and use them to help create core/window #2 with him leading the way. Or if you can't re-sign him, you keep them to kickstart a rebuild along with the assets you get from the next version of scorched earth.
You don't want to have this current season held hostage by what Matthews may or may not do, but I think that is unfortunately the situation. I truly believe if you re-sign him, you absolutely have a second window. Like Tampa, Washington, St. Louis and even Colorado (if you count their window starting after the Mackinnon draft, but since 2009 that team has been in a bizarre be amazing or totally tank phase like no other).
With what this team has shown us the past few years, I'm not willing to bet all the chips to try and salvage this current window. If this core had multiple deep runs and had just fallen short a few times, sure, that is another story. Make the bet. But at this point for me, you either save your chips for window/core #2 led by Matthews, or you save them for the post-Matthews era rebuild.