Exposing of the insensitive emails comes just days after it was revealed Gruden made a racist comment about the executive director of the NFL players union in 2011.
The NFL obtained the emails that Gruden sent to Bruce Allen, the former president of the Washington Football Team in a separate investigation of workplace misconduct regarding that franchise.
The Wall Street Journal reported Friday that Gruden used a racist comment to describe NFL Players Association leader DeMaurice Smith. Now, the latest emails reported by the Times showed Gruden denounced the drafting of a gay player and the tolerance of players protesting during the playing of the national anthem among other issues.
Gruden has apologized for his “insensitive remarks” about Smith, saying they were made out of frustration over the 2011 lockout. But the latest emails sent from between 2011-18 when Gruden was an analyst for ESPN show his use of derogatory language went well beyond that.
A league source confirms the accuracy of the emails and said they have been sent to the Raiders. The person spoke on condition of anonymity because the league hasn't made the emails public. The person said the league is awaiting for the team to review the emails and decide how to proceed.
Raiders owner Mark Davis said last week that the email about Smith was “disturbing and not what the Raiders stand for" and said the team was reviewing the additional emails. The team and Gruden didn't immediately respond for comment but Gruden said earlier Monday he learned from this, without going into detail.
“I’m not going to rehash the event again," Gruden said. “I think I feel very good about the things that I have learned. I also feel really good about what I stand for. I’ll be happy to talk about football, but I’ll just leave it at that.”
Gruden signed a 10-year contract worth up to $100 million to coach the Raiders in 2018.
The Times reported that Gruden used a gay slur to insult Goodell and said he was “clueless” and “anti-football.” He also said Goodell shouldn't have pressured the Rams to draft “queers," a reference to Michael Sam, who was the first openly gay player drafted by an NFL team.
Raiders defensive end Carl Nassib came out as gay in June and is the first openly gay player to appear in an NFL game.
In a 2017 email, the Times said Gruden responded to a sexist meme of a female official by saying: “Nice job roger.”
The paper also said Gruden criticized Goodell and the NFL league for trying to reduce concussions, and said that Eric Reid, a player who had demonstrated during the playing of the national anthem, should be fired.
The newspaper said Gruden also mocked an article in 2017 about players calling on Goodell to support their efforts promoting racial equality and criminal justice reform.
“He needs to hide in his concussion protocol tent,” Gruden wrote.
Gruden and Allen have a long relationship, having worked together in Oakland and Tampa Bay. The emails between the two and other men included photos of women wearing only bikini bottoms, including one photo of two Washington team cheerleaders.
Gruden also criticized President Barack Obama during his re-election campaign in 2012, and then-vice president Joe Biden.
Smith said earlier Monday that he appreciates that Gruden reached out to him following the initial report, but that the email is evidence that the fight against racism is ongoing.
“But make no mistake, the news is not about what is said in our private conversation, but what else is said by people who never thought they would be exposed and how they are going to be held to account,” Smith wrote in a Twitter thread.
Gruden’s comments to Allen about Smith came during the 2011 lockout of the players by the NFL. Gruden told the Wall Street Journal he was angry about the lockout during labor negotiations and he didn’t trust the direction the union was taking.
“Dumboriss Smith has lips the size of michellin tires,” Gruden wrote in the email reviewed by the newspaper.
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