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Sean Payton nearly became Cowboys coach in 2019; could it happen now?

Rich Eisen reacts to the breaking news that Sean Payton is reportedly stepping down from the Saints, recaps his 15 year career in New Orleans and wonders who may take his place with the team.

With Sean Payton stepping down as head coach of the Saints after 16 years on the job, his next move will become an issue of major intrigue and curiosity. There’s a sense he could land in television for a year or two, perhaps before returning to the NFL.

Or maybe he could simply resurface with a new team. Maybe sooner than later.

He has been linked to the Cowboys on various occasions in the past. He worked there as offensive coordinator under Bill Parcells, before getting the New Orleans job in 2006. Not long ago, Payton nearly became the head coach of the Cowboys.

What follows comes from my new book, Playmakers: How the NFL Really Works (And Doesn’t). The essay from which it’s drawn can be found there, if/when you purchase the book. (The book contains more than 100 total essays about the last 20 years in the NFL.) Consider this a taste, with the obvious goal being that perhaps you’ll decide to buy the whole pie.

The year was 2019. The month, January. The Cowboys had won 10 of 16 games, along with a wild-card contest against the Seahawks. They lost to the Rams in the divisional round, 30-22. Cowboys owner Jerry Jones contemplated an upgrade from coach Jason Garrett to Sean Payton. Jones wanted to pull the trigger. Payton did, too.

Things unfolded quickly. The Saints had played in the NFC Championship, losing to the Rams on January 20. That week, Jones quietly made his move.

It was a delicate situation, for various reasons. First, the Cowboys had a coach. Jones wouldn’t have fired Garrett unless he knew he could have gotten Payton. Second, league rules (specifically, the Rooney Rule) require a diverse and inclusive search. Third, Jones had to ultimately know that, after going through the motions of a search, he’d be able to get Payton.

So a deal was worked out, behind the scenes. The Saints would have allowed the Cowboys to hire Payton. The Cowboys would have compensated the Saints for the rights to Payton’s contract. And Payton would have signed a new contract with the Cowboys.

It was ready to go. It was happening. It was locked, and it was loaded. Then came Monday, January 28. On that day, New Orleans Pelicans forward Anthony Davis announced he would not sign another contract with the team, and he requested a trade. (In July, the Pelicans traded him to the Lakers.)

Gayle Benson owns both the Pelicans and the Saints. Saints G.M. Mickey Loomis was, as of January 2019, the executive vice president of basketball operations with the Pelicans. Once Davis made clear his intention to leave New Orleans, Loomis told Payton that Loomis couldn’t be the common thread between a pair of such high-profile Louisiana departures.

That ended it, just like that. The Saints were no longer interested in essentially trading Payton to the Cowboys. In September, Payton signed a new contract. That deal has three years left on it.

And, yes, Jones could once again fire up the behind-the-scenes engine in an effort to land Payton. It would be the same drill as three years ago, however. This time, an unexpected Pelicans-related complication wouldn’t get in the way.

If not now, then maybe 2023. Or 2024. Regardless, the Cowboys have a talented team. And Payton is keenly aware of the fact that no coach in NFL history has won a Super Bowl with two different franchises.

So there’s the story, courtesy of Playmakers. If that leaves you wanting the rest of the pie, well, dig in.