Gruden and Payton coached against each other twice a season from 2006-07 when Gruden was with the Tampa Bay Buccaneers and Payton was with the New Orleans Saints. They coached against each other one more time in 2020 when Gruden was with the Las Vegas Raiders.
Gruden and Payton will face off in a different way Thursday night. Gruden’s alma mater, the University of Dayton, opens the season against Payton’s alma mater, Eastern Illinois University, in Charleston, Ill.
Gruden will be at the game. Payton, now in his third season as head coach of the Denver Broncos, will be watching closely after making a bet with Gruden.
The coaches traded videos on social media Thursday.
“Coach Jon Gruden, hey, your best friend, Sean Payton here from the Denver Broncos,” Payton said. “My understanding is your Dayton Flyers travel to Charleston, Ill., to play the Eastern Illinois Panthers. And the reason I know that is Adam Trautman, one of our tight ends, is from Dayton as well. I’ve been tired of hearing his chirping.
“Big Game for both teams. My understanding is you’re going to be there on the sideline. I suggest we get a little bet going, a little wager. You know I like to watch that show of yours where you open the boxes that have been sent from everywhere in the country. My problem with that show is the tape cutter. It takes you forever to open the boxes, and I kind of need a tape cutter here, so we’re going to bet a high-tech tape cutter and dinner on this game tonight.”
Gruden, who now works for Barstool Sports, responded with a video he filmed by being driven around Charleston by Eastern Illinois athletic director Tom Michael.
“We are here,” Gruden said. “The Dayton Flyers are here. And I heard your bet. I’ll bet you a fancy box opener, and I want dinner in Shanahan’s restaurant in Denver. You know Mike Shanahan? Oh, he went to Eastern Illinois too, didn’t he? Let’s go Flyers. This is going to be a freaking big one. Love you, brother.”
I’m in Charleston, Illinois today to watch @EIU_FB play my alma mater @DaytonFootball
— Jon Gruden (@BarstoolGruden) August 28, 2025
My good friend Sean Payton is an EIU alum and just sent me this, a little friendly wager on tonight’s action.
Well Sean, YOU’RE ON! Can’t wait for tonight’s game!!! pic.twitter.com/c0BSq2eoK0
Tonight is gonna be a great game, can’t wait for that dinner @SeanPayton https://t.co/aObFIoPz6R pic.twitter.com/RjA17sNkn8
— Jon Gruden (@BarstoolGruden) August 28, 2025
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