Las Vegas Raiders head coach Jon Gruden has stepped down from the role following a trail of email leaks that show the 58-year-old making homophobic and misogynistic comments.
Gruden was already subject of an investigation after the Wall Street Journal reviewed a 2011 email, in which he referred to NFL Players Association executive director DeMaurice Smith (who is black) as "Dumboriss Smith."
He reportedly went on to write that Smith had "lips the size of michellin tires," although Gruden said he had no memory of writing the message, which was sent to a team executive.
That led to further analysis of 650,000 emails, and the New York Times uncovered numerous Gruden emails using homophobic and misogynistic language to insult individuals and changes happening around the league.
Among those comments, Gruden criticised a team's decision to draft an openly gay player, the NFL's promotion of female referees and players protesting the national anthem in the name of Black Lives Matter.
The Raiders released a statement late Monday confirming Gruden's exit, as the departing coach wrote: "I have resigned as head coach of the Las Vegas Raiders. 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."
NFLPA figurehead Smith took to social media following Gruden's resignation and said the two will talk soon after the former "reached out" to him, but he said the emails were proof "the fight against racism, racist tropes and intolerance is not over."
Former President of the United States, Barack Obama, was among Gruden's targets while he was running for re-election in 2012, when he also referred to then-Vice President Joe Biden as a "nervous clueless p****.”
NFL commissioner Roger Goodell was a frequent subject of Gruden's derogatory remarks, with the coach reportedly referring to him as “faggot” and a “clueless anti football pussy,” among other insults.
He also said Goodell shouldn't have pressured Jeff Fisher—who was at the time coach of the St. Louis Rams (now the Los Angeles Rams)—to draft "queers."
That was a reference to Michael Sam, the first openly gay player to be drafted by an NFL team (although he never made an NFL appearance).
Many of the emails in question were sent to former Washington Football Team president Bruce Allen and other team executives while Gruden was an ESPN analyst.
One of the messages saw Gruden send Allen and others an email that "included photos of women wearing only bikini bottoms," one of which pictured two Washington team cheerleaders.
He first coached the Raiders when they were based in Oakland, California, between 1998 and 2001, returning to the franchise in 2018 after a decade's break from coaching.
Gruden signed a 10-year, $100million contract to rejoin the Raiders, hoping to add another Super Bowl ring after winning American football's top prize with the Tampa Bay Buccaneers at the end of the 2002 season.
Las Vegas defensive end Carl Nassib became the first active NFL player to come out as gay in June, which led to an outpour of support from the NFL, the wider community and Raiders owner Mark Davis.
However, emails from 2015 showed Gruden asking Allen to tell Bryan Glazer—whose family own the Buccaneers—to perform oral sex on him.
Allen and Gruden also exchanged messages making fun of Caitlyn Jenner, who received an award from ESPN after she transitioned in the same year.
The Raiders’ special teams coordinator, Rich Bisaccia, has been appointed interim coach until the franchise decides on a long-term successor to Gruden.
