Las Vegas Raiders coach Jon Gruden resigned Monday evening after leaked private emails revealed he called Joe Biden a “nervous clueless pussy.”

The New York Times obtained a trove of emails showing Jon Gruden made so-called “misogynistic and homophobic” comments over the years.

Gruden lashed out at NFL Commissioner Roger Goodell and called him a “faggot” and a “clueless anti football pussy” according to emails reviewed by the New York Times.

Jon Gruden also exercised his First Amendment right and criticized Barack Obama and Joe Biden (gasp).

The New York Times reported:

When the vaunted N.F.L. coach Jon Gruden was confronted with a racist email he had sent in 2011 to insult the head of the players’ union, he said he went too far but didn’t have “a blade of racism” in him.

But league officials as part of a separate workplace misconduct investigation that did not directly involve him have found that Gruden, now the coach of the Las Vegas Raiders, casually and frequently unleashed misogynistic and homophobic language over several years to denigrate people around the game and to mock some of the league’s momentous changes.

Gruden’s messages were sent to Bruce Allen, the former president of the Washington Football Team, and others, while he was working for ESPN as a color analyst during “Monday Night Football,” the sports network’s weekly prime-time telecast of N.F.L. games. In the emails, Gruden called the league’s commissioner, Roger Goodell, a “faggot” and a “clueless anti football pussy” and said that Goodell should not have pressured Jeff Fisher, then the coach of the Rams, to draft “queers,” a reference to Michael Sam, a gay player chosen by the team in 2014.

Gruden also criticized President Obama during his re-election campaign in 2012, as well as then-vice president Joe Biden, whom Gruden called a “nervous clueless pussy.” He used similar words to describe Goodell and DeMaurice Smith, the executive director of the N.F.L. Players Association.

The league is already investigating Gruden as a result of another email he wrote to Allen in 2011 in which he used racist terms to describe Smith, who is Black.

In that email, Gruden, who is white and was working for ESPN at the time, criticized Smith’s intelligence and used a racist trope to describe his face. The correspondence was first reported by The Wall Street Journal and confirmed by The New York Times.