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Dee Winters #53 now of the Dallas Cowboys

New Dallas Cowboys linebacker Dee Winters has quite a bit in common with old (well, he’s been around the longest) Cowboys linebacker DeMarvion Overshown. Both are local products, with Winters having gone to TCU and Overshown to Texas. Both are in their third seasons, too, with much to prove. Overshown must show he can stay healthy for a full 17-game slate, while Winters needs to show that a breakout season for the 49ers in 2025 was not a fluke.

Most significantly, barring any further changes, the pair will need to show that they’re up to the task of filling in at linebacker, a position the Cowboys have had a difficult time filling in recent years–and a difficult time filling this season. Remember, Winters was not the Cowboys first choice. They pursued Devin Lloyd, Nakobe Dean and Quay Walker in free agency and had trade discussions about others around the league before finally scooping up Winters for a fifth-round pick.

Even now, there remain questions about the depth at linebacker, and indeed, questions are what binds the Winters-Overshown pairing.

DeMarvion Overshown, Dee Winters Up for Contract Extensions

And it’s those questions, too, that will dictate the business end of Winters and Overshown’s time in Dallas. Both are heading into Year 4 in the NFL, which means they can become free agents next season, or sign a contract extension with the Cowboys this offseason. There would be some logic on the Cowboys offering such a deal=–if both blossom in 2026, they could be locked into bargain deals.

But that’s one reason why it won’t happen. Extensions for either guy would be risky for both the team and the player.

Cowboys, Players Lack Incentive for New Deals

That’s the consensus from the Cowboys beat writers –Nick Eatman and Tommy Yarrish–at DallasCowboys.com. The question about extensions for Overshown and Winters were put to them, and quickly shot down.

As Eatman wrote: “In the case of these linebackers, neither has done enough yet to warrant a big-time extension. So if they signed now, it wouldn’t for top dollars. That’s why the agents for these guys are willing to bet on the player to go out in this ‘contract’ year and earn it. The player doesn’t want to sign too early and give up a lot of money they could make and the teams don’t want to overpay right now when the contract isn’t justified yet.

“So both sides wait and realize that a new contract doesn’t make sense at the moment. … For these guys, it has to play out because no one is going to accept the terms from the other side at this point.”

DeMarvion Overshown, Dee Winters in Critical Year

Winters is probably better positioned for a long-term contract at this point, whether with the Cowboys in 2027 or elsewhere. He played 17 games last year, filling in for 49ers star Fred Warner, and logged 101 tackles. Overshown, though, played only six games in 2026 recovering from a torn ACL, MCL and PCL.

He missed all of 2023 with a knee injury, too, and has just 19 games under his belt. The Cowboys are hopeful he still has star potential.

“I hope it’s big,” coach Brian Schottenheimer said in the winter when asked about what kind of leap Overshown can make. “We all know the impact he can have. The type of young man he is and the way that he prepares and works — I love his play style but I love his leadership. And I think … having a full offseason is something that should have him very excited because of the potential and the talent and the drive and work ethic and all of those things. I think he’s made of the right stuff.”