Former NFL MVP proposes a strange trade involving Dak Prescott to Jerry Jones that could worsen the Cowboys' situation

The Dallas Cowboys and Los Angeles Chargers have endured difficult starts to the 2026 NFL season, prompting former NFL MVP Boomer Esiason to suggest a dramatic solution: swapping their starting quarterbacks.

Esiason believes Dak Prescott could benefit from moving to Los Angeles , while Justin Herbert could give Dallas a new direction.

However, although the proposal would generate enormous headlines, it is far from certain that either franchise would improve by making such a significant change.

The Chargers entered Week 7 at 0-6, while Dallas sat at 2-4. Both teams have struggled to meet expectations, but their problems extend beyond the quarterback position.

Speaking on his Kickoff with Boomer and Valenti show, Esiason imagined what the unusual deal could look like.

"Could you see Justin Herbert wearing a Dallas Cowboys uniform? Let's just fantasize about that for a second," he said.

He then outlined the potential exchange: "I mean, Justin Herbert goes to the Cowboys , and Dak Prescott goes to the Chargers , that would be amazing. That would be great for the NFL, great for football. Now, both of these guys probably have 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. 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."

Why a Herbert-Prescott swap could backfire on Dallas

Herbert , 28, offers Dallas a younger quarterback who could potentially lead the franchise for years. Prescott , 33, brings greater experience, having spent his entire NFL career with the Cowboys since being drafted in 2016.

However, age alone does not make a trade worthwhile. Herbert would have to adjust to a new coaching staff, offensive system and supporting cast, while Prescott would face the same challenge in Los Angeles. Neither quarterback could guarantee an immediate turnaround.

The financial implications could also complicate negotiations. Prescott signed a four-year, $240 million extension in 2024, and Dallas restructured his contract in 2026 to create salary-cap space.

Those moves pushed significant cap obligations into future seasons, making any trade more complicated than simply exchanging quarterbacks.

There is also the question of whether Prescott is actually the Cowboys ' biggest problem. Dallas has struggled defensively, particularly on third downs, while offensive-line issues have added pressure on the attack. Replacing the quarterback would not automatically fix those weaknesses.

Jerry Jones has more immediate concerns

Prescott has already made clear that Dallas cannot afford to keep waiting for its season to improve.

"We can only say we've got a lot of games in front of us for so long. Might be already past us, right? We've got to go win," Prescott said, via ESPN.

"You've got to go win. You want to give yourself a chance to be a winning team, to be a playoff team. You got to win as many games as you can, and when you drop two games, in particular games that we didn't expect to drop, it makes it that much harder. So urgent, urgent to get it done now."

The Cowboys face Philadelphia on Monday night, October 26, in a divisional matchup that could help determine the direction of their season.

Both teams entered the contest at 2-4, making the result particularly important for their playoff ambitions.

For Jones , the priority should be addressing Dallas' broader problems rather than pursuing a headline-grabbing quarterback exchange.

Herbert's age and talent make the idea intriguing, but surrendering an established franchise quarterback could introduce fresh uncertainty at a time when the Cowboys need stability.

Esiason's proposal is an entertaining hypothetical, not a confirmed trade discussion. Unless both quarterbacks and both organisations were willing to consider such a move, it is unlikely to progress beyond debate.

For Dallas, the safer route may be improving the roster around Prescott instead of gambling that a different quarterback would solve everything.