Mailbag: Extend Overshown or Winters now?

(Editor's Note: Time to check the mail! The DallasCowboys.com staff writers answer your questions here in 'Mailbag' presented by Miller Lite.)

Since it's a contract year for both DeMarvion Overshown and Dee Winters, should Dallas extend one of them before the season starts, where it would cost the team less now? If they wait until the season is over, it may cost more if they have outstanding years. And wouldn't potentially losing both in free agency because they became too expensive put them in the same linebacking predicament next year? – George Abbot*/Homer, LA*

Nick: Let's look at it from both sides. Last year, both Jack Sanborn and Kenneth Murray were in their last years of a contract. It would've made sense to sign them to a long-term contract before the season, too.

Now, how would that have worked out? There is a reason that most players get to free agency without a new deal. Think about your own job - does anyone in the workplace truly feel like they're making as much as they think they're worth? On the flip side, the employers probably feel like the staff could do a little more based off what they're paying.

My point is that both sides usually don't agree on a contract negotiations and that's why it usually has to run its course.

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 other players after three years, such as Tyler Smith or Jake Ferguson, it made sense. Both had also already made a Pro Bowl. But for these guys, it has to play out because no one is going to accept the terms from the other side at this point.

Tommy: I see the point that you're trying to make and it's not a bad one. However, what have Overshown and Winters proven up to this point in their careers that would make you want to commit significant long-term capital at the position? That's not to say they're not good players. They certainly can be long term options at the position for Dallas. That said, there are still questions that loom heading into the 2026 season for both.

For Overshown, of course it's a question of health. With two major knee injuries in the rear view mirror and only 19 games played in three seasons, he needs to prove that he can stay healthy over the course of a season and still be able to tap into the game-changing speed and ability to fly across the field that made him explode onto the scene in 2024 before he was injured.

And for Winters, his 2025 season was the best of his career, but it's a question of whether or not he can continue to produce at that kind of level. It's somewhat similar to George Pickens' situation the sense that he's played at such a high level for one season, but I think the Cowboys want to see more of it before deciding on committing a large portion of the salary cap. Of course, Winters is a different situation because he hasn't played a game yet in a Cowboys uniform, but just in the sense of still having things to prove.