It can be easy to forget that when the Dallas Cowboys traded for George Pickens last offseason, it was seen as a huge risk.

Given George’s “antics” during his time with the Pittsburgh Steelers, there was a sense that the move could blow up in Dallas’ face.

Well, under Brian Schottenheimer, it didn’t.

Pickens would post 1,429 yards and 9 TDs en route to his first Pro Bowl nod as he developed into Dallas’ top offensive weapon in 2025.

Now, an impending free agent, the big discussion point is what the Cowboys should do with Pickens and his contract.

We know that the Cowboys’ plan, thanks to our own Mike Fisher, is to franchise tag him, which would give Pickens roughly $28 million for the 2026 season.

But what about a long-term deal? Insider Fisher predicts that could be four years and $120 million total. Yes, that would cost at least $30 million APY, but it would ease Pickens’ cap impact.

However, has Pickens done enough to warrant that sort of faith from Dallas?

ESPN’s Damien Woody thinks the Cowboys should want to see more.

“I would tag him,” Woody said on GetUp. “I would bascially say, show me again because I’m not dismissing the years he spent in Pittsburgh. It’s one thing to do it in a contract year, and you put up that type of season. I still need to see you do it again before I fully commit long-term to a player like George Pickens.”

Once again, George’s reputation precedes him.

But is what Woody said the smart thing to do? There is a risk that Pickens doesn’t play on the tag or even sign it, and then a whole can of worms gets opened up.

Given what he did for the offense in 2025, the Cowboys would be smart to keep Pickens around, but at an APY over $30 million?

That is the question Dallas has to ask itself.

Is what they saw from Pickens both on and off the field last season, given them enough confidence that George has turned the corner both professionally and personally?

Because when you are talking about paying a player over $30 million a season, there can’t be any doubts over said player.

Pickens quietened the skeptics in 2025, but it appears that if he wants the long-term deal he’s after, he might have to do it again.

Whether he likes it or not.