The NFL revealed Wednesday that former head coach Jon Gruden sent inappropriate emails throughout his tenure with the Oakland Raiders. Gruden is suing the NFL and accusing the league of fabricating a campaign to fire him.

Gruden’s conduct over email between 2010 and 2018 came to light in October 2021, but the NFL is now alleging that his behavior persisted during his tenure in Oakland.

Gruden’s 2021 resignation came in the wake of a league investigation for workplace misconduct. League officials found that Gruden used homophobic, racist and misogynistic language in emails as the coach of the Washington Football Team.

These emails were leaked to the New York Times and Wall Street Journal. Though the revelation led Gruden to step down soon after signing to be the Raiders’ head coach, he has since sued the NFL for targeting him unfairly in the investigation and creating a situation necessitating a “forced resignation.”

The NFL’s decision to now reveal Gruden’s emails in Oakland appears to be an attempt by the league to dissuade the former coach from pursuing further legal action.

A judge denied the league’s motion to dismiss the case in June. The NFL’s new findings also challenge Gruden’s timeline of events, as the coach claims that much of the NFL’s investigation applied to years in which he was working as an ESPN employee.

League attorneys have consistently argued that officials have the right to punish misconduct within organizations, but Gruden has argued that the NFL’s treatment led directly to the destruction of his career and assassination of his character.

Though the NFL investigated 650,000 emails within the Washington organization between 2010 and 2018, only Gruden has been punished for communications sent in that span.

Dan Snyder, another target of the investigation, continues to own the team now known as the Washington Commanders despite testifying before Congress for harassment claims last month.

As the league continues to pursue options to avoid a trial, Gruden’s time as an NFL coach has become increasingly public. Many of the phrases he used in emails, which he has admitted to sending, have not been read in court due to their inappropriate nature.

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