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Extending George Pickens now would be a mistake

Originally posted on Inside The Star
By Richard Paolinelli | Last updated Jun 7, 2025 10:08 AM ET

There’s been some talk recently about the Dallas Cowboys extending newly acquired receiver George Pickens right now.

He hasn’t even played a single down in Dallas yet, but sure, let’s sign him to a big deal. That would be a foolish move.

You have to look no further back than last year to see why this is so.

Prove It Deals Are Best

Last year, the Cowboys waited until a few hours before opening kickoff to sign quarterback Dak Prescott to an extension rather than let him play out the final year of his deal.

Prescott lasted all of eight games in 2024 after signing a deal in the neighborhood of $60 million a year through the 2028 season.

The Cowboys definitely didn’t get their money’s worth last year. Prescott is still not fully recovered from what was his third leg injury of his career.

So who knows if he’ll come back this year anywhere close to what he’s been in the past?

Had Dallas told Prescott to “prove it” last year instead, they would still probably have re-signed him this offseason. But at a much more team-friendly price.

Right now, Prescott is making more per year than five other starting quarterbacks who have either won Super Bowls (Patrick Mahomes and Jalen Hurts) or at least gotten his team to one (Jared Goff, Joe Burrow, and Brock Purdy).

Two others, Josh Allen and Lamar Jackson, have at least made it to a conference title game. Clearly, the Cowboys overpaid.

They don’t need to do it again with Pickens.

Pay The Man, Later

If Pickens does come in and has a stellar season as the Cowboys WR2, then pay the man.

It sounds like that’s what he wants to do anyway. It’s a smart move on his part.

Could Dallas save some money by extending him now? Sure, but what if they do and he pulls an Antonio Brown midway through the season?

Or blows out an ACL four games in?

Now you’re on the hook, without a legit WR2, and with no cap room to go get one next year.

Madness.

Time To Break Patterns

Jerry Jones has a long history of overpaying players at the wrong time. His insistence on paying “on the come” is one of many reasons why it has nearly been 30 years since the team last won a Divisional round playoff game.

The most recent examples are Michael Gallup and Terence Steele.

Gallup is trying to make an NFL comeback in Washington. Steele remains in Dallas but is in jeopardy of losing his job as the starting right tackle.

Both were big-money contracts signed after big leg injuries.

Neither has paid off.

So don’t make the same mistake again with Pickens. Let this season play out and then pay the man what he’s worth after.

This article first appeared on Inside The Star and was syndicated with permission.

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