Jon Gruden, who recently resigned from his position as head coach of the Las Vegas Raiders after the revelation of emails using racial and misogynistic language, once called Joe Biden a “nervous clueless p*ssy.”

Gruden reportedly made the comment in an email exchange with former Washington Football Team General Manager Bruce Allen. Gruden also referred to NFL Commissioner Roger Goodell as a “f*gg*t” and “clueless anti football p*ssy.”

The email exchange with Allen, which was unearthed as part of a misconduct investigation that did not directly involve Gruden, took place over the course of seven years, from 2011-2018, according to the New York Times.

LAS VEGAS, NEVADA – OCTOBER 10: Head coach Jon Gruden of the Las Vegas Raiders talks to his players as they stretch before a game against the Chicago Bears at Allegiant Stadium on October 10, 2021 in Las Vegas, Nevada. The Bears defeated the Raiders 20-9. (Photo by Ethan Miller/Getty Images)

According to the emails, Gruden also said that the then-St. Louis Rams should not have been pressured into drafting “queers,” referring to Michael Sam, the first openly gay player to enter the NFL Draft.

In another exchange, Gruden said that NFL Players Association President DeMaurice Smith, who is black, had lips the size of “michellin tires.”

LAS VEGAS, NEVADA – SEPTEMBER 26: Head coach Jon Gruden of the Las Vegas Raiders argues a call during the second half of a game against the Miami Dolphins at Allegiant Stadium on September 26, 2021 in Las Vegas, Nevada. The Raiders defeated the Dolphins 31-28 in overtime. (Photo by Chris Unger/Getty Images)

When asked about the comment, Gruden said he often refers to people as having “rubber lips” when he believes they are lying.

Gruden resigned from his position Monday night due to mounting pressure due to the emails.

“I love the Raiders and do not want to be a distraction,” Gruden said in a statement Monday night. “Thank you to all the players, coaches, staff, and fans of Raider Nation. I’m sorry, I never meant to hurt anyone.”

Gruden was 22-30 since returning t the sidelines as Raiders head coach in 2018. Gruden’s first head coaching job was also with the Raiders. A position he held until 2002 when he left to take over the Buccaneers.