Mailbag: Smart to sign Pickens now?

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

Would it be smart to give George Pickens a contract extension now? My fear is that after a big year he'll get a big contract once he becomes a free agent at the end of the season. He and CeeDee Lamb could be a dynamic duo for years to come. – Frank Biehn/Chandler, AZ

Nick: I think it's smart to sign all of your unrestricted guys as early as you want. But as we've found out already - especially with this particular agent - it takes two sides to make a deal.

And yes, Pickens is represented by the same agency as Micah Parsons, but that doesn't mean it will be the same situation. But just remember this, if you try to sign a player early, any agent is going to project the rest of the season. Right now, you're looking at Pickens catching around 75 passes for 1300 yards and about 12 TDs - that's just a projection for the rest of the season. What else would an agent have to use? So that being said, it's not going to be cheap right now either.

And the problem is, the money you have to give Pickens might be more than CeeDee's current contract and you know that won't go over that well. There is an option to franchise Pickens at the end of the season and sometimes that can be used as just a placeholder to get a deal done later in the offseason and protect themselves with a possible first-round pick if someone wants to sign him away.

For me, you've already lost one great player to another team this year. I don't think I'd get in the habit of doing it. One way or another, I'd try to sign him, whether it's now or later. Personally, I think it might be cheaper if you waited ti the end of the season.

Kurt: There are a lot of facets to this. It's easy to think that giving Pickens a contract extension as soon as possible would be the smart path to take. As we've all seen, he's an exciting receiver who is one half of perhaps the best pass-catching combo in the NFL.

And with those like Dak Prescott, CeeDee Lamb, Jake Ferguson, Tyler Smith, Tyler Booker and Terence Steele already locked up, adding Pickens into that mix would surely open wide the window for a Super Bowl-caliber offense through at least 2028.

Ah, but what about the defense? Can the Cowboys afford Pickens and what would be a receiver room topping $60 million when so much help is needed on the other side of the ball? Even if they just used the franchise tag for one year, would that be the smart play?

Then again, it takes two to tango. Is signing now and not testing the free-agent market next spring really smart on the part of Pickens? Here's guessing his agent, the same group who represented Micah Parsons, thinks not.

And if that's the case, would the Cowboys entertain thoughts of trading him now for a high draft pick instead of potentially having to settle for a third-round compensation pick in the 2027 draft? I don't think that will happen, but if the team loses its next two games before the trade deadline and truly doesn't believe it can get Pickens re-signed in any way down the road, that might actually be the smart move.

So while we would all love to see Pickens and Lamb dicing up opposing secondaries for years to come, getting any type of deal done soon appears doubtful. If the Cowboys really want him, they can figure out the salary-cap gymnastics. If they wanted to shock us and trade him, that can happen too.

No matter what path they take, though, they just have to be smart about it.