Sources: Cowboys & Dak Prescott Ready to Start Contract Talks as Deadline Looms

Sources: Dallas Cowboys & Dak Prescott Ready to Start Contract Talks as Deadline Looms

FRISCO - Upon the Jones family’s takeover of the Dallas Cowboys, Jerry and oldest son Stephen immersed themselves as quickly as possible into the day-to-day operations of an NFL franchise.

Among the focus points for Stephen: Learning the art of contract negotiations from team exec Bob Ackles, a key aide to GM Tex Schramm.

And among the lessons stressed by the late Ackles to a then-25-year-old Stephen?

“The first guy to pick up the phone,” Ackles said, “just lost the negotiations.”

Some things about “The Art of the Deal” have changed in 30 years, thanks to free agency and the salary cap. Indeed, part of Ackles’ job back then was to save the owner’s cash; now it’s about cap allocation.

But ultimately, it’s still about “winning” - which brings us to “Dak Prescott vs. the Cowboys” … and negotiations we are told are about to get underway.

Sources told us early this week that the two sides are “ready” to visit, and the calendar tells us the same thing. 

Yes, we are aware of what appears to be a Saturday “shoot-down” of our reporting, ESPN’s Jeremy Fowler writing that the two sides have yet to engage in “substantial” negotiations.

We won’t debate that. We won’t argue about what “substantial” means. The two sides entered the week “ready” to launch into talks.

That’s our story. We stand by our reporting.

The quarterback is entering the final year of his four-year, $160 million deal he signed in 2021. Prescott currently has a $59.4 million cap hit in 2024, and while the Cowboys could leave that be, doing so would a) hinder their ability to spend elsewhere in roster-building and b) mean Dak will be free to leave Dallas in free agency after 2024.

That was not Dallas’ original plan; the idea was always to restructure. But especially if agent Todd France pushes for Prescott to become the highest-paid player in NFL history (at say $60 million APY?), Dallas could balk and take its chances.

There is a third option, which involves moving the money by adding voidable years. That’s a Band-aid as it would buy Dallas cap room with Prescott playing as a lame duck.

The answers aren't clear but the negotiating arguments might be. France gets to say that Dak was an MVP runner-up with league-leading numbers in touchdown passes and QBR. The Cowboys can counter by using their fancy new word “holistic” and push for Dak to compromise away from eating up a massive chunk of the cap pie.

And all along looms the extension timetable. Dallas must be cap-compliant by March 13. Yes, there are other ways to get there. But put simply, optimally, a decision on Prescott’s money must be made by that date. And it almost certainly must change by that date.

Is Dak “worth” the same as top-paid QBs Joe Burrow ($55 million APY) and Lamar Jackson and Justin Herbert ($52 million APY)? That’s not really the point.

This negotiation is going to be about the cost of doing “star QB” business … and whether Dallas chooses to do it long-term.

'Choir Boy!' Stephen A. Smith Blasts Dak Prescott

And it will be about a ticking clock, which is why a negotiation-launching phone call is about to be made. 

"Once the season is over, we will focus on that,'' Stephen said a little while back in previewing what's to come. "Dak will be our quarterback."

Bob Ackles taught of a “Game of Chicken”-like philosophy; It still applies. Jerry has a related mindset, framed by one of his most famous quotes: “Deadlines make deals.”

But now March 13 is on the horizon. Somebody’s got to call somebody. Because the deadline is coming.