Why now? What is the benefit? They've already bypassed free agency. They have 12M in cap space.
If they don't sign him now, there are 2 scenarios:
1: Dak & the Cowboys win the Super Bowl.
2: Dak sucks in the playoffs and/or regular season.
If scenario 2 happens, then I prefer they let him move on.
If scenario 1 happens, then his market price is still set by last QB that signed the biggest contract.
- Tua is not going to get radically more than Trevor Lawrence.
- If Mahomes was in the last year of his contract, then I would worry about the market jumping radically above 55M; however Mahomes is signed for several more seasons.
If Dak hits free agency, the Cowboys likely only have to match the best offer.
- Dak will make far more in endorsements as the Cowboys QB than anywhere else.
These are not the only two scenarios, that is a false dichotomy.
Here are the actual scenarios and there are many.
1. Dak plays statistically the same as last year and the Cowboys fail to make the playoffs due to defense falling off with Quinn leaving.
2. Dak plays statistically the same as last year and the Cowboys make the playoffs, but lose in the first or second round.
3 Dak plays statistically the same as last year and the Cowboys make it to the SuperBowl.
4. Dak plays statistically worse than last year and the Cowboys fail to make the playoffs.
5. Dak plays statistically worse than last year and the Cowboys still make the playoffs but lose in the first or second round.
6. Dak plays statistically worse than last year but the Cowboys still make the NFCCG or SB due to an outstanding defense.
7. Dak could become injured during the season.
That right there is seven possible scenarios where Dak plays anywhere from totally sucking to being in the MVP race to being injured, so there are many, many more scenarios than just the two you listed where Dak and the Cowboys either win the SB or Dak sucks.