Jon Gruden frequently used misogynistic and anti-gay language in numerous emails during the seven-year period before he was hired as coach of the Raiders in 2018, The New York Times reported Monday night, saying it has reviewed the emails.
The NFL sent the Raiders additional Gruden emails to review, on top of the one about NFL Players Association executive director DeMaurice Smith that surfaced last week, and others Gruden recently confirmed to ESPN, sources told ESPN's Adam Schefter on Monday.
According to The Times, Gruden sent emails to Bruce Allen, then the president of the Washington Football Team, and others during a seven-year period that began in 2011.
The Times reported that Gruden used an anti-gay slur in several instances to insult NFL commissioner Roger 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 in 2014.
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 reported that Gruden criticized Goodell and the NFL for trying to reduce concussions, and said that Eric Reid, a player who had demonstrated during the playing of the national anthem by taking a knee, 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 was employed by ESPN as the lead analyst for Monday Night Football at the time he sent the emails now under review.
"The comments are clearly repugnant under any circumstance," ESPN said in a statement.
The Wall Street Journal reported Friday afternoon that one of Gruden's emails from 2011 included a racist comment in reference to Smith. Gruden, who had given his players a heads-up Friday morning that the Journal's report would be coming out, apologized for his "insensitive remarks'' about Smith, saying they were made out of frustration over the 2011 lockout and not trusting the direction the union was taking. But the additional emails sent between 2011 and 2018 show his use of derogatory language went well beyond that.
Gruden's emails came to light during the NFL's investigation of workplace misconduct with the Washington Football Team, as "the league was informed of the existence of emails that raised issues beyond the scope of that investigation," according to NFL spokesman Brian McCarthy. Senior league executives reviewed the content of more than 650,000 emails, including ones between Gruden and Allen. The NFL sent pertinent emails to the Raiders for review.
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 led the Raiders from 1998 until he was traded to Tampa Bay after the 2001 season. He immediately led the Buccaneers to a Super Bowl title -- against the Raiders.
He lasted through the 2008 season in Tampa before being fired, then headed to the Monday Night Football booth.
The Raiders, then in Oakland, rehired Gruden in 2018 with a 10-year, $100 million contract. The team moved to Las Vegas last year and has not made the playoffs since his return. The Raiders are 3-2 in 2021.
Raiders owner Mark Davis said last week that the email about Smith was "disturbing and not what the Raiders stand for," while McCarthy condemned the email and said it was "appalling, abhorrent and wholly contrary to the NFL's values."
ESPN's Paul Gutierrez and The Associated Press contributed to this report.