Sean Payton’s retirement from the New Orleans Saints sent shockwaves through the NFL yesterday. Not only was the head coach’s exit a surprise, but the notion that he could potentially join the Dallas Cowboys is now one of the hottest topics in sports.

Payton was part of Bill Parcells’ overhaul of the Cowboys’ staff in 2003, joining the team as the quarterbacks coach as an assistant head coach. He spent three years working with Quincy Carter, Vinny Testaverde, and Drew Bledsoe as Parcells helped Dallas get back to relevance.

Arguably Sean’s greatest contribution to the Cowboys occurred behind the scenes. As a fellow product of Eastern Illinois, Payton was aware of a little-known Panthers QB named Tony Romo. The story’s always been that Sean was instrumental in getting the undrafted Romo to Dallas in 2003 and developing him for the eventual takeover of the starting job in 2006.

Unfortunately, Payton left for the Saints’ head coaching job in 2006 and never got to work with Romo as QB1. But it’s been fairly common knowledge that Jerry Jones has always regretted losing Payton from the organization and would love to get him back into the fold.

In fact, according to a new revelation from NFC Sports’ Mike Florio, Jones’ desire to reunite with Payton nearly came to fruition in 2019.

In the aftermath of the Cowboys’ disappointing playoff exit in 2018, Jerry supposedly had a deal worked out with the Saints to trade for Sean Payton and dump Jason Garrett. But because of joint ownership and management between the Saints the New Orleans’ NBA team the Pelicans, issues with former Pelicans’ star Anthony Davis were creating too much negative press for the Saints to then deliver another crushing blow to their community.

Was it as close to happening as Florio states? Was it even remotely on the table? Only Mike and the parties involved know for sure, but even a modicum of truth in this story speaks to Jones’ desire to have Payton as his head coach.

Now it’s not like Sean Payton is free to hire right now. He retired with three years left on his contract, meaning the Saints would have to release him and likely expect compensation for doing so from now through 2024.

Dallas’ current head coach, Mike McCarthy, also has three years on his deal. But unlike the issues that come with releasing and signing players, there’s no salary cap for coaches and executives. The Cowboys can fire McCarthy anytime they want.

It’s somewhat hard to believe we’re already talking about moving on from McCarthy. after just two seasons. But after two years of very Jason Garrett-like results since his arrival, Mike hasn’t done much to show he was the upgrade at head coach that the Jones family was expecting.

Would Sean Payton take things to another level? There’s plenty of room for debate on that topic, but what ultimately matters is what Jerry Jones believes.

Also relevant is the degree to which New Orleans would want to be compensated for releasing Payton from his contract. They may be friendlier than some teams given Sean’s enormous contributions to the franchise and the community during the last 15 years, but all that goodwill could quickly go out the window in the name of NFC competition..

Also, let’s be clear, Payton’s supposed reason for “retiring” was to step away from the rigors of coaching. He may be moving into a television role while he rests and considers future options, if he intends to return to the NFL at all.

So no, this is far from a done deal or even the first step in the process. There may be no process or connection between Sean Payton and the Dallas Cowboys now or in the future.

But if there’s anything to all of these stories and history, Jerry Jones might be willing to do a lot to make it happen.