Dak Prescott has etched his name in the Dallas Cowboys' record books as the all-time leader in passing yardage and passing touchdowns. He's proven to be a strong leader of the franchise and has guided them to a record of 85-59-1 in his career.

The problem is that he hasn't had success in the postseason. Dallas is just 2-5 with Prescott as the starter during the playoffs, something that has haunted him throughout his career. While Jerry Jones and the front office have always supported Prescott despite the playoff losses, he can't escape the criticism.

Now, Prescott is struggling in the regular season as well, leading Dallas to a record of 9-13-1 since the start of the 2025 season. That had Mike Valenti asking Boomer Esiason if the Cowboys need to move on from Prescott. Esiason didn't outright say it was time, but floated a wild trade idea, that even he admitted isn't likely to happen.

"Did you see Justin Herbert wearing a Dallas Cowboys uniform? Let's just fantasize about that for a second. I can see it. I mean, Justin Herbert goes to the Cowboys and Dak Prescott goes to the Chargers. That would be amazing. That would be great for NFL. That would be great for football," Esiason said on their show, Kickoff with Boomer and Valenti.

"Now, both of these guys probably have no move clauses or no trade clauses in their contracts, but maybe both of the guys are sick and tired of where they are by the time we get to the end of the season. So I think that would be a dream scenario for all of us who cover the NFL. I don't know that would help. And I don't think Dak is going anywhere."

Justin Herbert for Dak Prescott would be an odd move for both teams

Aside from the fact that neither team would realistically be able to move on from their star quarterbacks, the trade makes very little sense for either franchise.

For the Chargers, they would be moving on from a 28-year-old quarterback who might be struggling in 2026, but is still in his prime. He might benefit from a fresh start, but Los Angeles wouldn't be willing to swap him for a more expensive player who is 33.

Dallas likely wouldn't be too quick to make the move. Sure, Herbert is younger, but he has the same issues Prescott does. Despite having multiple seasons with double-digit wins, Herbert is just 0-3 in the postseason and had a historically bad performance in 2024 when he threw four interceptions in a loss to the Houston Texans.

You could make an argument that due to his age, Herbert would be a better option. That said, they already know and trust Dak, which makes it far more likely in their minds that they can find success with him at the helm than with a player they don't know.