Cowboys Trade Dak Prescott for QB Justin Fields? NFL Draft ‘What-If?’ Analysis

The Dallas Cowboys are faced with a contract dilemma surrounding quarterback Dak Prescott. If things go south, could he be traded for Justin Fields?

Dallas Cowboys quarterback Dak Prescott is coming off the best season of his career, and yet, a segment of the fanbase has reached its breaking point. Another 12-5 season — Dallas’ third in a row — has ended in utter disaster and ended a three-year run with just a single playoff win.

For some, the criticism has shifted past whether or not Prescott is the franchise guy and a good one at that. Throwing for 4.516 yards and 36 touchdowns, that debate has largely subsided, outside of national punditry and the Cowboys Industrial Complex it accentuates. Now, the question becomes if this core, with this coaching staff, will be enough to win a Super Bowl. Stars need to be paid, generational talents are aging out, and Dallas still hasn’t made a conference game.

With Prescott’s nearly $60 million cap hit looming, the Cowboys have some important decisions to make. They can get clever with his contract, which has one year remaining to help alleviate a chunk of that cap hit. They could also extend him in. It’s the simplest way to stay relatively competitive, though it will come at a price. They cannot trade him without his approval. They cannot tag him. In all likelihood, Dak Prescott is going to be the highest-paid quarterback in football.

Chicago Bears quarterback Justin Fields / Mandatory Credit: Mike Dinovo-USA TODAY Sports

For those queasy about an even longer-term commitment to Prescott, pushing the reset button may be preferable. KD Drummond explored this possibility when looking at a possible swap of quarterbacks between Dallas and the Chicago Bears. There’s no better time to get weird than the offseason, and when it comes to what these teams are going to do in April, it’s all just guesswork anyway.

In short, if things go south, and Prescott is willing to accept the Windy City as a trade destination, he’ll be paid handsomely, and the Cowboys will, too. Dallas would be receiving Bears quarterback Justin Fields, along with a smattering of picks — one of which would also be used on a first-round quarterback. The full ramifications of the deal can be found here; it’s an interesting thought exercise that is worth your time.

The Cowboys would be able to put Fields behind the best offensive line of his career and, if the defense comes back strong, could still compete for a playoff spot. If Fields flames out, the rookie can start in 2025 after marinating for a season. This gives them flexibility and a chance at a somewhat cost-controlled star quarterback.

However, exploring the Prescott trade market may best serve as a reminder that Dallas should prioritize giving him a blank check and figuring out the rest. There is no quarterback available this offseason that gives the Cowboys a better chance at a Super Bowl than Prescott does. There’s a reason for that — quarterbacks good enough to eventually bring a Lombardi Trophy home generally don’t get moved.

Prescott may not be as game-breakingly talented as the stars that can win out of thin air, but there are numbers here. Should head coach Mike McCarthy be criticized for not giving him the best chance to rack up playoff wins? Maybe, though this was again the No. 1 offense in the NFL. But yes … For all the production it helped generate, the “Texas Coast Offense” didn’t work when needed most.

We bet QB-needy teams would nevertheless want Dak if free.

It’s easy to imagine a Prescott free agency tour, complete with jersey swaps with the Miami Dolphins or the Atlanta Falcons or whomever and the passing production that would follow. He’s good enough to win, the onus is on the Cowboys to make Dallas the place where that’s possible.

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Almost every off-ramp from the Prescott experience (including an immediate reliance on unproven Trey Lance) is a quick road to uncertainty and quarterback purgatory. A rookie quarterback can turn out to be a franchise quarterback and still not be as good as the passer that preceded him. The dead cap from Prescott’s deal would mitigate the cap relief his absence would provide, too.

The Cowboys must look in the mirror and make some tough decisions, both this year and next. Unless Prescott is forcing his way out, it’s hard to conjure up a scenario where moving on is anywhere close to preferable.