Say what you want about Jerry Jones, but his teams haven't come up short lately for a lack of effort. Sure, you can call out his cheapness when it comes to head coaches, but the Dallas Cowboys' owner and GM wheels and deals more than any other decision-maker in the league.
He never leaves a stone unturned.
This offseason, part of that attempt to make the Cowboys better was making not one, but two deals with the devil: the San Francisco 49ers. Although these two franchises have long been rivals, they found a way to make what they deemed at the time to be two fair trades that benefited both.
Have they, though?
It's not always easy to tell from afar. But the two teams face off in Week 10 at AT&T Stadium on Sunday afternoon, which will give Jones a unique chance to evaluate the trading of Osa Odighizuwa and the acquisition of Dee Winters, both of which occurred this past spring.
49ers' Osa Odighizuwa could give Cowboys a healthy dose of regret
After signing a four-year, $80 million contract extension in March of 2024, Dallas dealt Odighizuwa to San Francisco in March of 2025. Considering the Cowboys' difficult financial situation, his underperformance, and the additions of Kenny Clark and Quinnen Williams, he was quite expendable.
Dallas did net a third-round pick for Odighizuwa, which was used on Jaishawn Barham. And while that seemed like a major win at some points early this season, in recent weeks, Barham has been benched, knocking some of the luster off the deal before Sunday even comes.
If Odighizuwa has a big game against the Cowboys, which is possible after Dallas' guards struggled up front last week against the Indianapolis Colts, then perhaps Jones could have a bit of remorse. To be fair, Odighizuwa is the same player that he was: A good pass-rusher and bad against the run.
It's not like, with Williams, Clark, Elijah Garcia, Otito Ogbonnia and LT Overton, Dallas is short on talent at the defensive tackle position. But it always feels bad to have a former player show out against the Cowboys, and with Barham's role all but evaporated, noise could leak in if Odighizuwa plays well.
Dallas needs former San Francisco LB Dee Winters to show out vs. his former team
Winters was acquired by the Cowboys on Day 2 of the 2026 NFL Draft, as Dallas sent a fifth-round pick to the 49ers. Clearly, the intent was to boost the linebacker corps with the additions of Barham and Winters, and that was not a bad idea. Helping out Christian Parker was a necessity.
But that plan was better on paper than it has been in practice.
Of course, Barham has had his moments, as has Winters, but neither has really taken the reins and been a difference-maker in the middle of the Dallas defense. Winters has had a bigger role, and he's played a bit better in recent weeks than he did to begin the year. But the body of work is still rough.
He has struggled in coverage all year, outside of a big interception against the Green Bay Packers, and Winters has missed 13.6 percent of his tackles on the year. It's been rough without DeMarvion Overshown next to him, but Shemar James has actually played well enough in his place.
If Winters struggles once again versus the 49ers' passing attack, which is likely with George Kittle and Christian McCaffrey being his main matchups, then the Cowboys will feel even more like they threw a fifth-rounder away. It'll feel even worse with San Francisco exploiting him from the opposite sideline.
Ideally, Barham and Winters both ball out, and Odighizuwa is limited by the Tylers up front. That way, regardless of the score, Jones can at least feel like he got a victory over 49ers general manager John Lynch. If not, heads may begin rolling in Dallas.
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