Last-minute leverage might work against Cowboys in Pickens deal talks

Chick-fil-A has a reputation for being obnoxiously friendly. Patagonia has a reputation for being abnormally reputable. J.P Morgan has a reputation for being concerningly savvy. And the Dallas Cowboys have a reputation for being eleventh-hour negotiators. All of the above entities have earned these perceptions, and in one way or another, all of them have made it work for them in their respective area of industry.

The Cowboys, unfortunately, are fast becoming victims of their own reputation and are now being forced to deal with the consequences in the George Pickens situation. They say, “deadlines make deals,” and by they, I mean Jerry and Stephen Jones. These front office power brokers pride themselves on their sticktoitiveness and intestinal fortitude during negotiations.

Not wanting to be the side that picks up the phone first, the Joneses have no problem sitting back silently for weeks, and even months, if it means gaining the upper hand. Waiting until the eleventh hour is hardly a tactic of their own creation. Some of the best dealmakers on the planet follow some form of this philosophy.

They know a looming deadline makes people uncomfortable and this discomfort might prompt some of those people to settle. The problem the Cowboys must deal with is everyone knows this is their philosophy, therefore opposing sides have no reason to take anything seriously that comes in before the eleventh hour.

HUGE day for George Pickens 9 catches, 168 yards, TD DALvsCAR on FOX/FOX One https://t.co/HkKw7uXVnt pic.twitter.com/nQnwftb1Hh — NFL (@NFL) October 12, 2025 In the case of Pickens and his agency, Athletes First, they know the best offer is yet to come and that day will be far, far down the road from today.

Where some teams like to get ahead of deals and ink long-term commitments as quickly as possible, teams like the Cowboys notoriously drag things out to the end. Sometimes they get done, as in the case of Dak Prescott and CeeDee Lamb. Sometimes they boil over and end in a split, as was the case with Micah Parsons. To be fair, in some cases the Cowboys have re-signed players early.

Trevon Diggs, Terence Steele and DaRon Bland were all signed well before their deals ran out. But those were situations of different leverage because they were players still under contract, and frankly, they were deals that didn’t turn out so great for Dallas. In situations in which the leverage is more evenly split and a deadline is in sight, the Cowboys tend to push the limits.

It means no one will take them seriously until the eleventh hour. Even if the Joneses want to make a legitimate offer to Pickens later this month, there’s no reason for Pickens’ side to think it’s the front office's best effort. Based on Dallas’ reputation, Pickens’ side has every reason to hold out until a time they expect the Cowboys to really make their best offer.

It’s that pesky reputation of theirs working against them. You can follow Reid on X  @ReidDHanson  and be sure to follow  Cowboys Wire on Facebook  to join in on the conversation with fellow fans!

This article originally appeared on Cowboys Wire: The Cowboys problematic reputation impacts George Pickens talks Even if the Cowboys wanted to change and offer a realistic new contract to George Pickens early in the offseason, their reputation blocks them Even if the Cowboys wanted to change and offer a realistic new contract to George Pickens early in the offseason, their reputation blocks them