The Super Bowl-winning Gruden was a Monday Night Football analyst in 2011 when he sent an email that, as The Wall Street Journal revealed Friday, used a racist trope to describe NFL Players Association president DeMaurice Smith, who is Black. “Dumboriss Smith has lips the size of michellin tires," Gruden wrote in the email. Gruden later apologized. On Monday evening, just as Monday Night Football was about to kick off, The New York Times reported that from 2011 to 2018, Gruden sent emails calling NFL commissioner Roger Goodell as a “f*ggot” and a “clueless anti football p*ssy" and used the word "queers" in response to Michael Sam being drafted as the first openly gay player in NFL history. Gruden also denounced the emergence of women as referees. The homophobic comments emerged months after Gruden expressed support for Raiders player Carl Nassib, who last month became the first openly gay player to play in a regular season NFL game. Gruden's emails were mostly sent to then-Washington Redskins general manager Bruce Allen, his close friend and former colleague. They were uncovered as part of a probe of 650,000 emails investigating allegations of workplace misconduct in the offices of the now-Washington Football Team. Gruden resigned in the fourth season of a $100 million, 10-year contract. He had a 22-31 record in his second stint as Raiders head coach. As The Athletic's Marcus Thompson III points out, Gruden betrayed the Raiders’ legacy of respect and inclusion. The Raiders hired the first Black head coach in NFL history, the second Latino head coach and the first woman as CEO, as well as having the aforementioned first openly gay player to be part of the regular roster.
ESPN has yet to respond to Jon Gruden's newly revealed emails: "Got to think a statement from ESPN is coming at some point in the second half. They’ve definitely glossed over the fact that this behavior was mostly during his tenure at ESPN," tweeted Awful Announcing. Before Gruden's resignation, ESPN did say in reaction to the DeMaurice comment: "The comments are clearly repugnant under any circumstance." Gruden worked on Monday Night Football from 2009 to 2017.
NBC Sports' Mike Tirico and Tony Dungy criticized for defending Jon Gruden over his racist remark: During NBC's Football Night in America, Tirico, who worked with Gruden in the Monday Night Football booth, when he sent the racist email, and Dungy, who was replaced by Gruden as Tampa Bay Buccaneers head coach after the 2002 season, defended Gruden. “I was with Jon at that time,” Tirico said. “Seven years as my partner on Monday Night Football. I probably know Jon better than anybody in the league on a personal level. He said it right, he was ashamed by the comments in the email. The comments in the email are wrong.” Dungy added: “He said that it wasn’t racial, he was making a comment about DeMaurice Smith, and he basically attacked his character. I will accept that and just say it was an immature way to do it. It wasn’t the right way to do it. But it was 10 years ago. And I’m not going to chalk everything up to racism. I think we accept his apology, move forward and move on.” Following Gruden's resignation, both Tirico and Dungy faced criticism on Twitter for being quick to defend Gruden. As former NFL player turned football blogger Stephen White put it: "There was literally no reason for Dungy nor Tirico to try to shield Gruden last night. That was a choice. And one that is rightfully gonna bite them both in the a**."