Some of the harmful content in the emails written by Gruden include him calling NFL commissioner Roger Goodell a "f*****" and also a "clueless anti-football pussy."
It is reported that he used that same homophobic slur several times when referring to Goodell.
In another email, Gruden referred to the openly gay Michael Sam as "a queer."
He also used a racist term to describe NFL union chief DeMaurice Smith in a 2011 email to former Washington executive Bruce Allen.
One email saw Gruden refer to then Vice-President Joe Biden as a "nervous clueless pussy" while exchanging photos of topless women.
Among the 650,000 emails sifted through were a handful of emails sent from former Washington executive Bruce Allen to Jon Gruden containing images of topless team cheerleaders, who were forced to pose topless against their will during a photoshop in the Costa Rica.