Jon Gruden's tenure with the Las Vegas Raiders is over after four years.

Gruden announced his resignation in a statement Monday night after emails uncovered from his past included racist, anti-gay and misogynistic language, per Ken Belson and Katherine Rosman of the New York Times.

Shortly afterward, Raiders owner Mark Davis said in a statement that he had accepted Gruden's resignation.

Tom Pelissero of the NFL Network first reported Gruden was planning to resign.

Suzy Kolber of ESPN (via Adam Schefter of ESPN) reported assistant head coach and special teams coach Rich Bisaccia will be the interim head coach

According to Belson and Rosman, Gruden "denounced the emergence of women as referees, the drafting of a gay player and the tolerance of players protesting during the playing of the national anthem." He also "exchanged emails with [former Washington Football Team president Bruce Allen] and other men that included photos of women wearing only bikini bottoms, including one photo of two Washington team cheerleaders."

He also used racist tropes to describe NFLPA executive director DeMaurice Smith.

The 58-year-old returned to the sidelines after a decade working in television when the Raiders agreed to a 10-year deal worth $100 million. He was extremely confident in his abilities when discussing the massive contract.

"If I can't get it done, I'm not going to take their money," the coach said before his first game in 2018, per Jarrett Bell of USA Today.

But Gruden's tenure offered more bad than good. After a massive rebuild during the 2018 campaign that included trading away Khalil Mack and Amari Cooper, things started to turn for the better in recent years, as the Raiders became more competitive.

There were higher expectations in 2020 with the franchise's move to Las Vegas, and the team matched it on the field with a 6-3 start, including a road upset win over the Kansas City Chiefs.

But things deteriorated in the second half of the year with a stretch of five losses in six games to put the team out of playoff contention before the season-ending win.

A come-from-behind win over the New York Jets saved what would have been an even worse collapse to the season.

It was the second straight late-season slide after the Raiders lost five of six to end the 2019 campaign. The team has started 3-2 in the 2021 season.

Overall, the Raiders went 22-31 in Gruden's second tenure.

There is still a lot of talent on the roster, but the organization must find a new leader to help reach expectations.