The Cowboys Lost In week 1 to the New York Giants.

Is this Dak Prescott’s last chance to change how Cowboys fans remember his career?

Dak enters the 2026 season with a 2-7 career playoff record, back-to-back losing seasons and one of the biggest contracts in NFL history. But he may also be playing some of the best football of his career and could have a legitimate MVP-caliber season ahead of him.

So how much is actually riding on this year?

Gavin Dawson of 105.3 The Fan is joined by former GBAG Nation personality Walt Chism and Kendrick Roberts of Best For Business to debate Dak Prescott’s legacy, his shrinking championship window and what it would take to finally end the argument about him in Dallas.

Is a trip to the NFC Championship Game enough? Does he need to reach a Super Bowl? And what happens if Dak plays great again but the Cowboys organization lets him down?

We also get into George Pickens’ future, Dak’s contract and age, the Cowboys’ roster construction, his playoff failures, the ways Dallas has failed its quarterback — and whether this season could represent his “last best chance” to change everything.

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