(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.