Jon Gruden Resigns as Raiders Coach After Bigoted Emails Surface

Jon Gruden's second tenure as head coach of the NFL's Raiders franchise ended with his resignation Monday, following days of media reports that he sent racist, homophobic and misogynistic messages via email from 2011 to 2018.

"I have resigned as Head Coach of the Las Vegas Raiders. I love the Raiders and do not want to be a distraction," Gruden said in a statement Monday night, as reported by ESPN. "Thank you to all the players, coaches, staff and fans of Raider Nation. I'm sorry, I never meant to hurt anyone."

Gruden, 58, agreed to a 10-year contract worth a reported $100 million in 2018. He had previously served as Raiders head coach from 1998 to 2001, when — in a rare personnel move for a coach — he was traded to the Tampa Bay Buccaneers. His Bucs defeated the Raiders in Super Bowl XXXVII on Jan. 26, 2003.

A career that also included a stint as color analyst in ESPN's Monday Night Football booth, when the emails in question were sent, began to unravel Friday, when The Wall Street Journal reported that Gruden had sent an email to Bruce Allen, then the president of the NFL's Washington franchise, in which Gruden said NFL Players Association executive director DeMaurice Smith had "lips the size of michellin tires."

On Monday, The New York Times followed with equally damning reports on the email correspondence between Gruden and Allen. Gruden reportedly referred to NFL commissioner Roger Goodell as a "clueless anti football p---y" and a "f----t."

Moreover, Gruden emailed Allen that Goodell should not have pressured then-Rams coach Jeff Fisher to draft "queers," referring to former defensive end Michael Sam, a gay player drafted in 2014, according to the Times, which also reported that Gruden used an anti-gay slur in several instances while referring to Goodell, and used offensive language to describe some owners, coaches and media members who cover the league.

As reported by ESPN, the emails came to light during the NFL's investigation into workplace misconduct with Washington, as "the league was informed of the existence of emails that raised issues beyond the scope of that investigation," according to NFL spokesperson Brian McCarthy. Senior league executives reviewed the content of more than 650,000 emails, including the one the Journal reported was written by Gruden to Allen. The NFL sent pertinent emails to the Raiders for review.

Gruden told ESPN that he routinely used the term "rubber lips" to "refer to a guy I catch as lying ... he can't spit it out."

"I'm ashamed I insulted De Smith. I never had a racial thought when I used it," Gruden told his former network employer. "I'm embarrassed by what's out there. I certainly never meant for it to sound that bad."

In Gruden's second stint with the team, the Raiders had gone 22-31. According to ESPN's Adam Schefter, Rich Bisaccia will take over this season's 3-2 team as interim head coach.