In fact, you only have to go back a few years, as both men left their respective jobs in 2021 — Payton by choice, while Gruden was forced out following some leaked emails that included racist and sexist comments.
Speaking of those emails, they’ve become an interesting topic of discussion once again, as they helped open up a gigantic can of worms that’s expected to result in the ousting of Dan Snyder from his position as owner of the Washington Commanders.
ESPN recently released an in-depth story on how Gruden’s leaked emails have resulted in the fall of Snyder. The piece includes an interesting little tidbit that doesn’t seem to have much to do with Snyder’s inevitable removal, but we’re glad they mentioned it anyway.
That’s because it talks about how then-Saints and current Denver Broncos head coach Sean Payton hilariously roasted then-Raiders head coach Jon Gruden for paying those ridiculous Covid fines that the league used to hand out to coaches for wearing their masks inappropriately.
The league fined the Raiders $500,000, fined Gruden $150,000 and stripped the team of a sixth-round draft pick for COVID-19 violations — and that was after the league had fined the team and Gruden a total of $350,000 for violations earlier in the season. (
Davis offered to pay Gruden’s $150,000 fine, but league officials insisted Gruden pay it personally, which he did.) Livid, Gruden appealed the fines but ended up writing the checks. After he did, his friend Sean Payton, then the Saints’ coach and who also had been fined for COVID-19 violations, called him and laughed.
“I never paid the fine,” Payton told Gruden, adding that other coaches also refused to pay. “You’re the only dumb F that paid the fine.”
Following that Covid-affected 2020 season, Payton would go on to coach the Saints for one more year before calling it quits. But after sitting out the 2022 campaign, he decided to return and was sent by the Saints to the Denver Broncos in exchange for a first-round pick.
As for Gruden, he’s still involved in an ugly legal battle with the NFL over what he believes was a wrongful dismissal. Maybe once everything gets worked out between Chucky and the league, we’ll see him and Payton coaching battling it out on the NFL’s sidelines once again.
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