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Cowboys' Jerry Jones would be wise to wave the white flag like Howie Roseman

It's funny now. But will it be down the road?
ByLevi Dombro
Dallas Cowboys owner Jerry Jones
Dallas Cowboys owner Jerry Jones | IMAGN IMAGES via Reuters Connect

An unsightly win over the Indianapolis Colts doesn't really change who the Dallas Cowboys are at this point under Brian Schottenheimer. And while Jerry Jones is busy entertaining the possibility of big moves at the trade deadline as he tries to salvage this season, his rivals might be lapping him.

The New York Giants are in the driver's seat for the NFC East, and Dallas has only a prayer of making it to the postseason as a Wild Card team. With a quarterback like Dak Prescott, you don't need to tank and bottom out, but the Cowboys might be better off doing a bit of future planning right now.

That's what the Philadelphia Eagles are doing.

Their trading Jordan Davis on Monday gave supporters of America's Team a good chuckle, as their bitter foe, which has dominated the division and league for way too long, fell from grace and threw in the towel on the season. But if Jones isn't careful, Howie Roseman will be the one laughing later.

Yet again.

Cowboys might need to follow in Eagles' footsteps and stockpile picks

After trading A.J. Brown this offseason, Philadelphia also dealt Cam Jurgens and Davis to amass 10 picks in the first two rounds of the next three drafts. Every April through 2029, Roseman and the Eagles will have major ammunition to fire, and that is a scary sight for Dallas, which is all-in right now.

Has Philly hit on every early-round draft pick in recent years? No; Roseman's perception as a gold miner of college prospects has fallen by the wayside a bit. But with enough bites at the apple, he is going to get a handful of difference-makers to supplement what is still an undeniably strong core.

While the Eagles aren't really in a ton of cap trouble next season, they have kicked the can down the road for years, and their day of reckoning may have been near. But Roseman is hedging against any potential trouble that this could cause by offloading some expensive players and stockpiling picks.

For a team that isn't going anywhere in 2026, that is not a bad strategy. Is Philly mathematically eliminated? Of course not. The NFC East is still, in many ways, wide open. The Eagles could easily justify buying at the deadline and trying to rescue this season. But Roseman is smarter than that.

Or at least he doesn't have too much pride. Let's hope that Jerry Jones comes to his senses in a hurry and ends up feeling the same way.

Why Jerry Jones should flip the script and sell at the trade deadline

Dallas isn't going anywhere fast with Schottenheimer running things. A trip to the playoffs that is earned by wading through shallow divisional waters will be futile if a shellacking awaits them in the Wild Card round. And it would prolong the Schotty nightmare Cowboys fans can't wake up from.

So, without completely calling it quits, Dallas could get rid of a handful of players and at least add to their four-pick 2027 draft capital. Perhaps a George Pickens trade is too rich, but the Cowboys have several other tradeable pieces, like Kenny Clark, Malik Hooker, T.J. Bass and DeMarvion Overshown.

Clark's timeline doesn't really match up with Dallas', and the latter three aren't exactly key pieces in whatever the Cowboys are building. Hooker is aging, Bass knows he can start elsewhere, and Overshown hasn't proven that he can stay healthy enough to warrant a long-term deal.

Getting a pick or two for these players, while also simplifying the Dallas financial equation that is not talked about enough and is anything but straightforward, might be a good process for Jones and the front office to follow. A minor hit in the short term to paint a brighter picture for the future.

Again, it was funny to see the Eagles turn around and trade a guy that they extended to a big-money deal just eight months ago, and the realization that Philly had packed it in for 2026 was satisfying in a lot of ways for Cowboys fans. But it may not be so funny looking back on it in a few months or years.

Howie Roseman is taking this season as a battle lost, because he knows that there are still many wars to win. He is waving the white flag so he can replenish his troops and go back to the drawing board so that he can devise a different strategy.

Jones doesn't seem like the type to do that, though, unfortunately. So, we may have to laugh now and cry later.

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