Sean Payton’s NFL playing career was about as short as they come. He played just three games with the Chicago Bears during the 1987 players’ strike. But as a coach, that’s where things got really interesting. After nine years molding college talent, especially quarterbacks and offensive guys, Payton broke into the league with the Eagles as a QB coach in 1997 under offensive coordinator Jon Gruden, soaking up everything he could.
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Two years in Philly, the City of Brotherly Love, and he was on the move again. Next stop … New York. Payton spent four years with the Giants, starting out as the quarterbacks coach before getting bumped up to offensive coordinator. He even helped lead them to the Super Bowl in 2001, where they ran into Ray Lewis and that ferocious Ravens defense.
By then, Payton’s stock was on the rise. And sure enough, he landed with the Dallas Cowboys as assistant head coach and QB coach under Bill Parcells. The turnaround was real too, as the Cowboys jumped from a 5-11 record the year before to 10-6 in 2003. They got bounced in the first round of the playoffs by the Panthers, but Payton showed he was the real deal and looked every bit like a future head coach.
Payton got his first call for the head job from Al Davis, the legendary owner and GM of the Oakland Raiders. It was right after the 2003 season, when the team had canned Bill Callahan in December. Callahan had just taken them to a Super Bowl the year before, but guys like Charles Woodson and Rich Gannon weren’t shy about ripping him publicly.
The locker room chaos carried over into a brutal record the next year. Davis knew he had a mess on his hands … and Payton made his shortlist.
“Bill [Parcells] comes to see me. And he says, ‘Al Davis wants to interview you for the head job.’ And he said, ‘I’m gonna be honest with you, I think he’s gonna wanna hire you,” Payton recalled on an episode of The Schrager Hour.
And sure enough, Payton got the call. He flew out to Oakland, spent three days with Al Davis, and then headed back home. Next stop was a family trip to Disneyland, but even there, his phone kept buzzing, late-night talks with Davis about staff members and whatnot, you name it. The way it was going down, Payton figured this was it … his shot at that first head coaching gig.
“I went to Jos. A. Bank and got my black suit with the silver tie,” Payton remembered. Yes, he was that sure he was getting hired.
During that trip, on a Thursday, Payton got a call from Michael Lombardi, the Raiders’ senior personnel exec, saying Davis wanted to speed things up. So, Payton hopped back on a call with Davis and ended up spending another three days in Oakland. Parcells, meanwhile, wanted a straight answer from Payton.
If the Raiders gig didn’t come through (which Parcells was basically betting on), he’d get to keep Payton in the coaching lounge. Parcells even told him over the phone something like, ‘Look, turning down a head coaching job isn’t easy, but stay with us anyway.’
Regardless, nothing was set in stone, and it looked like Payton was packing for Oakland. But then, Jerry Jones did what Jerry does best … he stepped in and convinced Payton to stay.
“When [me and Parcells] hung up, two minutes later, the phone rang and it was Jerry. And he asked me to come by the house. He sent a driver. And I think it was the same type of trip that Zim [Mike Zimmer] took. There’s a moral of this story: If Jerry’s the last guy you see, you’re probably staying.”
Sean Payton was thisssss close to being the head coach of the Raiders.
Then, Jerry Jones got in the way.
First time Sean’s ever told this story…
Coach Payton was an awesome guest on the first episode of “The Schrager Hour”. Click the link here: https://t.co/2FJ99nsMWV pic.twitter.com/Rsvfp8NmH8
— Peter Schrager (@PSchrags) September 3, 2025
Jerry Jones was really something back then. And you know, Cowboys fans would love to have that old Jerry back, the one who’d do whatever it took to keep his coaches and players around. If that Jerry was still running the show, Micah Parsons probably wouldn’t be going anywhere.
That said, Payton spent the next two years in Dallas before landing his first head coaching job with the Seattle Seahawks. He won AP Coach of the Year in his very first season (2006) and went on to hoist a Super Bowl trophy just three years later.