Think we need to decide if we are in a rebuild or not first.
And IMO, Jerry signalled that we are "all in", whatever that means in Jerry speak.
I would support a rebuild, but let's be honest, that is not happening, so I believe the best option is to think of ways this team can improve, within the confines of our current constraints.
Zach will be restructured, freeing up some money.
Dak will either be extended long term, or at the very least will have a few void years added to free up some money.
If I was negotiating, I'd tell Dak no way are you getting 55-60. Mahomes makes 45 (and sorry Dak, you're no Mahomes). You were overpaid on the last contract, and I understand you can't take less for appearences sake, so I'll give you 45 APY on an extension.
Take it or give me a list of teams you'll accept a trade to.
But we all know Jerry will cave.
I completely disagree with this 'next man up sets the market" philosophy of NFL contracts. It really is an agent inspired theme.
But France will say "Herbert got this, Burrow got this, Lamar got this, so we want this as the cap has risen".
The Cowboys need to realize Dak has serious limitations. Sportrac has Cousins valued at 39, that is in the ballpark of what Dak should command. (One could even argue that as the face of the Cowboys he will earn 5-10 mil more in endorsements that a peer).
Still Dak (and France) can't take less than his previous deal, so to me 45 is a fair number given Jerry's decision to keep the team together. To me, for Dak to be making what Mahomes makes is honor to Dak (that he doesn;t deserve). The GOAT took way less his entire career because he understood that to win, one must make some sacrifices. Dak (and Todd France) need to learn this.
Sadly, we all know how this goes. Jerry will cave, Dak will get 55+ and we will lose in the first round again.