Jon Gruden email scandal: Timeline of events that led to Raiders HC's resignation

To say it has been a tumultuous couple of days for Jon Gruden would be an understatement. Now, having officially resigned as Raiders head coach last night, more of Gruden's misdemeanors are coming to light and it does not make for pleasant reading.

It all came to a head when Gruden's emails were uncovered as part of an investigation into the Washington Football Team's president Bruce Allen's workplace misconduct and, ever since, a whirlwind of information has been released.

Timeline of events leading to Gruden's resignation

It all started last Friday when The Wall Street Journal reported that it had uncovered an email in which Gruden had stated that Demaurice Smith, the NFLPA Executive Director, had "lips the size of Michellin (sic) tires."

That in itself was enough to bring down condemnation upon Gruden and could potentially have seen him resign or be fired. As expected, Gruden tried to walk back on the comments by stating that he uses the words “rubber lips” to call a person a liar. On Sunday he did apologize for the remarks he made, but as we now know, that was the tip of a rather slippery iceberg.

So with the NFL community and the world population as a whole reeling from Gruden's email, halfway through Monday Night Football, another bomb was dropped.

Gruden's next batch of emails exposed

The New York Times released a report that the NFL had uncovered even more emails that involved Gruden through a period from 2010 to 2018, in which Gruden had used homophobic, sexist and transphobic language.

This was all before Gruden was hired by the Raiders for his second coaching stint with the franchise. According to the Times, Gruden called Roger Goodell, the NFL commissioner a “f—t” and a “clueless anti football p—y.” However, it didn’t stop there. Gruden also employed several homophobic slurs that were used to describe some NFL coaches, owners and others who cover the league.

If that wasn’t enough, there is more. Gruden reportedly sent emails to Bruce Allen that had photos of cheerleaders from the Washington Football Team who were only in bikini bottoms.

But Gruden and Allen weren’t the only people included. Ed Droste, the co-founder of Hooters, and Jim McVay, an executive who ran the Outback Bowl, and lastly Nick Reader who is the founder of the PDQ Restaurants were part of the group. All of the exchanges between the men started in 2010 when Gruden was employed by ESPN as an analyst for Monday Night Football.

In 2017, according to the Times, Droste shared a meme that was sexist of a woman refereeing in the NFL to which Gruden replied, “Nice job roger”.

Gruden also had his two cents on several issues outside the NFL as he reportedly criticized Barack Obama’s reelection in 2012 while calling the then vice-president Joe Biden a “nervous clueless p—y.” Gruden also criticized the league for trying to reduce concussions and finally added that Eric Reid, who demonstrated against police brutality during the national anthem, should be fired.

It all ended at 8 pm Monday night, in which Jon Gruden resigned as coach of the Raiders to complete a whirlwind couple of days.