Last year it didn’t work out well with pass rusher Micah Parsons, who got into a public war of words with Jones over a lucrative extension. That beef was over Jones directly discussing a deal with Parsons instead of his agent, something the owner hasn’t shied away from doing in his past.

The irony is that Pickens is represented by the same agent, David Mulugheta, so more fireworks could be on the way. The team does have the franchise tag at their disposal and will use it, if necessary, but the hope is a deal can be worked out.

Extending Pickens is priority number one for the Cowboys, so it could be a long, drawn out process to get him a new contract.

New deals for Javonte Williams and Brandon Aubrey

Not far behind Pickens, are possible new deals for the Cowboys’ leading rusher and their All-Pro kicker. Finally healthy, Williams had a breakout season in Dallas, and he’ll be just 26 years old heading into the 2026 campaign. That’s still in the prime for a running back and while there’s mutual interest in re-signing Williams, nothing’s a given with the Cowboys.

The same can be said for Aubrey, a restriced free agent, who has been a revelation since becoming the Cowboys’ kicker. A deal for Aubrey is likely to come and should be easy since it’s not a massive deal, but these things don’t always go smoothly with this front office.