I don't think he's going to sign an extension since neither side seems willing to budge. Jerry may cave, Dak won't because he has no reason to do it.
I expect he'll get tagged. Whether that leads to a trade, who knows? I can't see the Cowboys letting him walk in 2021. They may have little choice in 2022.
They won't have any choice in 2022. They either come to an agreement this offseason or there won't be a long term deal with him. Both sides know this.
Part of this stems from Booger caving with star players in the past. France stonewalled them and his guy got 31.4M and he can do the same and he gets 37.7M this year. Then he gets to negotiate with any team, after averaging 34.5M for 2 years. If they tag him, he drags down 21% of the 2021 cap. That doesn't leave a lot with quite a few players up.
If that's me, I don't tag him. I re-sign Dalton and focus on young defensive players in FA and the draft and might even consider taking a QB with that 1st. I might even consider trading Lamb and my 10th to NYJ and taking Wilson. I don't think JAX will trade with a new HC that needs to win over the fans. I use Dalton as a short bridge to work Wilson into the QB1 role to see if I need to do the same thing in 2022. I would be relentless, can't win it without that top 5 trigger man. I'd keep picking until I found him.