I think the main reason that the Cowboys haven’t resigned Dak to a new contract is his impact on the salary CAP - not so much this year’s CAP, but the CAP for future seasons.
The Cowboys need to clear his 59M off the CAP this year, rather than kick the can down the road yet again. This is also the last year for the big contracts for Zach Martin, and DeMarcus Lawrence.
In order to set themselves up for CAP success in future seasons, AND also to have enough CAP space to sign Micah Parsons to a long term deal, they need to clear the CAP in future years. So, by letting Dak play out the final year of his contract this season, the Cowboys free themselves of a lot of rollover CAP charges they would incur by signing Dak now.
Finally, if you listen to Dak’s latest comments to the press, he says he understands what they are doing from a business perspective. And Jerry has explicitly said the failure to sign Dak this year isn’t because they don’t value Dak; rather, it is about CAP management.
Ultimately , if the Cowboys want to keep Dak (and I believe they do want Dak back), then it will cost them more in real dollars by waiting until next year. But the name of the game is CAP management. They run the risk of alienating Dak; but on the other hand, they believe Dak wants to be in Dallas, and will forgive them.
Trey Lance is their backup plan. You can see he has the physical tools to be a successful NFL QB. His arm strength and elusiveness jump out at you when you watch him. But he’s reckless with the ball - something Dak isn’t. If Dak leaves, the Cowboys will keep Lance on a cheap contract, hoping they can coach the recklessness out of him. But they’d rather have Dak.
The bottom line is the NFL economics is forcing the Cowboys to “reset” their CAP for future seasons. That is why they are choosing to take the big CAP hit for Dak this year - hoping they can fix it all next March.
At least that is my theory, based on looking at the contracts, future CAP space, and the comments coming from both Jerry and Dak.