Jon Gruden's Emails Reveal a Pattern of Discriminatory Speech Over Seven Years
Jon Gruden's emails indicated a history of discriminatory views.
Published Aug. 12 2025, 12:51 p.m. ET

It's fair to say that Jon Gruden's tenure as an NFL head coach was rocky both on and off the field. The former head coach of the Raiders was known to make controversial remarks, and that was before The New York Times published a report about his emails in 2021 that further damaged Gruden's reputation in the world of professional sports.
Gruden has since sued the NFL for the leak of the emails, suggesting that it was done intentionally to damage his reputation. Given how much of a big deal has been made of these emails over the years, many people naturally wonder what's in them. Here's what we know.

What did Jon Gruden's emails say?
According to reporting from The New York Times, the emails spanned a seven-year period from 2011 to 2018, and were addressed to Bruce Allen, then the president of the Washington Commanders, among other people. Apparently, Gruden used an anti-gay slur to refer to NFL Commissioner Roger Goodell, and said that he was "clueless'' and "anti-football." He also said that the NFL should not have pressured the Raiders to draft "queers,'' a reference to Michael Sam, who was drafted in 2014.
In a 2017 email, Gruden reportedly responded to a sexist meme about a female official by saying, "Nice job Roger," apparently blaming the commissioner for hiring female officials.
He also said that Eric Reid, a player on the Raiders who had knelt during the national anthem, should be fired, and criticized Goodell and the NFL for working to reduce concussions amongst players.
In a separate email, Gruden made a racist comment about the NFL Players Association executive director, DeMaurice Smith. Gruden, who knew that the email about Smith would be released, gave his players a heads-up and apologized, saying that at the time he was frustrated by the 2011 lockout and was not confident in the direction that the union was taking. Gruden eventually stepped down as the team's coach following the revelation of these emails.
Jon Gruden recently notched a victory in his lawsuit against the NFL.
Although he lost his coaching job, Gruden recently won a victory in the Nevada Supreme Court, per ESPN. The Court ruled 5-2 that the league's decision to force his complaint into arbitration proceedings overseen by NFL commissioner Roger Goodell — the target of Gruden's civil lawsuit — was "unconscionable."
They did not offer any findings on the claim that the NFL had leaked the emails.
Gruden should not have been involved in arbitration because, at the time of the incident, he was a former employee and therefore not bound by the rules of the NFL Constitution. The NFL's only remaining avenue is an appeal to the U.S. Supreme Court.
"We're very pleased with the Nevada Supreme Court's decision, not just for Coach Gruden but for all employees facing an employer's unfair arbitration process," said Adam Hosmer-Henner of McDonald Carano LLP, attorneys for Jon Gruden. "This victory further vindicates Coach Gruden's reputation, and it clears the way to swiftly bringing him full justice and holding the NFL accountable."