Updated

Jon Gruden and the Las Vegas Raiders are heading their separate ways.

Gruden stepped down as the Raiders’ head coach on Monday night after The New York Times reported that the longtime coach made racist, misogynistic and homophobic comments directed at Commissioner Roger Goodell and NFL Players Association Executive Director DeMaurice Smith, among others.

CLICK HERE FOR MORE SPORTS COVERAGE ON FOXNEWS.COM

Gruden sent emails to former Washington Football Team president Bruce Allen between 2010 and 2018.

The NFL Network first reported the news of Gruden's resignation.

Head coach Jon Gruden of the Las Vegas Raiders talks with quarterback Derek Carr #4 during their 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. 

Head coach Jon Gruden of the Las Vegas Raiders talks with quarterback Derek Carr #4 during their 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 Ethan Miller/Getty Images)

Gruden, who was in the fourth year of a 10-year, $100 million contract, released a statement following the decision to resign.

"I have resigned as Head Coach of the Las Vegas Raiders," Gruden said. "I love the Raiders and do not want to be a distraction. Thank you to all the players, coaches, staff, and fans of Raider Nation. I’m sorry, I never meant to hurt anyone."

There was a ton of reaction to the Gruden news on social media.

RAIDERS HEAD COACH RESIGNS AFTER HOMOPHOBIC, MISOGYNISTIC EMAILS REVEALED

According to The New York Times, Gruden called Goodell an anti-gay slur and a "clueless anti-football p---y"  in at least one email and argued that Goodell shouldn’t have allegedly pressured then-St. Louis Rams coach Jeff Fisher to draft "queers," in reference to former NFL defensive lineman Michael Sam who was the first openly gay player to be selected in the draft.

Las Vegas Raiders head coach Jon Gruden speaks on his headset during the first half of an NFL football game against the Chicago Bears, Sunday, Oct. 10, 2021, in Las Vegas.

Las Vegas Raiders head coach Jon Gruden speaks on his headset during the first half of an NFL football game against the Chicago Bears, Sunday, Oct. 10, 2021, in Las Vegas. (AP Photo/Rick Scuteri)

The email appeared to show a complete disconnect from Gruden’s messaging when his own player Carl Nassib came out as gay before the start of the 2021 season and became the first active openly gay NFL player.

Gruden also reportedly made remarks about Smith, saying, "Dumboriss Smith has lips the size of Michelin tires."

Gruden criticized the league for hiring female referees. In 2015, Sarah Thomas became the first permanent female official in league history. In 2017, The New York Times reported Gruden replied to an allegedly sexist meme from Hooters co-founder Ed Droste about female NFL officials and replied, "nice job roger."

DEMAURICE SMITH: JON GRUDEN EMAIL SCANDAL CONFIRMS ‘FIGHT AGAINST RACISM’ NOT OVER

The newspaper reported that Gruden wrote that former defensive back Eric Reid should have been fired for protesting during the national anthem. He also criticized a bill that would’ve forced the then-Washington Redskins to change their name in 2015, Caitlyn Jenner, and he criticized former President Barack Obama during his re-election campaign in 2012, and then-vice president Joe Biden.

Jon Gruden of the Las Vegas Raiders in action against the Pittsburgh Steelers on September 19, 2021 at Heinz Field in Pittsburgh, Pennsylvania. 

Jon Gruden of the Las Vegas Raiders in action against the Pittsburgh Steelers on September 19, 2021 at Heinz Field in Pittsburgh, Pennsylvania.  (Photo by Justin K. Aller/Getty Images)

CLICK HERE TO GET THE FOX NEWS APP

Raiders owner Mark Davis said last week that the email about Smith was "disturbing and not what the Raiders stand for" and said the team was reviewing the additional emails.

Raiders assistant coach Rich Bisaccia was named the team’s interim head coach.

Fox News' Ryan Gaydos contributed to this report.