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New on SI: Report: Jon Gruden Repeatedly Used Misogynistic, Anti-LGBTQ Comments in Emails

An NFL investigation has uncovered numerous conversations in which Jon Gruden frequently used misogynistic and anti-LGBTQ language.

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Days after news broke of Raiders head coach Jon Gruden's reported use of a racist trope to describe NFLPA executive director DeMaurice Smith, The New York Times has shared more emails from Gruden that show a pattern of offensive and inappropriate language.

Shortly after the report came to light, Gruden reportedly informed the Raiders of his plans to resign, per NFL Network's Tom Pelissero.

In reviewing more than 650,000 emails sent over the past decade, the NFL has reportedly found numerous examples of Gruden using misogynistic and anti-LGBTQ comments, according to Ken Belson and Katherine Rosman of The New York Times. The findings come as a result of the league's separate workplace misconduct investigation into the Washington Football Team.

In many of the emails in question, Gruden corresponds with former Washington team president Bruce Allen, among others. Gruden and Allen worked together in Gruden's first stint as Raiders coach and with the Buccaneers. The emails occurred when Gruden was working at ESPN. Gruden used his personal email account, while Allen used his team account.

Among the findings, Gruden reportedly expressed his disapproval of the NFL's hiring of women as referees, drafting gay players and tolerating players who protested during the playing of the national anthem. He also criticized commissioner Roger Goodell for placing an emphasis on player safety, referring to him by an anti-LGBTQ slur and calling him a "clueless anti football p----."

Gruden also derided Goodell for, as he viewed it, pressuring then-Rams head coach Jeff Fisher into drafting "queers," a reference to the Rams selecting Michael Sam as the first publicly gay player in NFL draft history.

In June, Raiders defensive end Carl Nassib became the first active NFL player to declare he is gay.

According to the Times, Gruden also mocked Caitlyn Jenner following her transition, and also responded to a sexist meme of a female referee by saying, "Nice job Roger."

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