From the NYT article:
Gruden's messages were sent to Bruce Allen, the former president of the Washington Football Team, and others, while he was working for ESPN as a color analyst during "Monday Night Football," the sports network's weekly prime-time telecast of N.F.L. games. In the emails, Gruden called the league's commissioner, Roger Goodell, a "f$ggot" and a "clueless anti football pssy" and said that Goodell should not have pressured Jeff Fisher, then the coach of the Rams, to draft "queers," a reference to Michael Sam, a gay player chosen by the team in 2014.
In numerous emails during a seven-year period ending in early 2018, Gruden criticized Goodell and the league for trying to reduce concussions and said that Eric Reid, a player who had demonstrated during the playing of the national anthem, should be fired. In several instances, Gruden used a homophobic slur to refer to Goodell and offensive language to describe some N.F.L. owners, coaches and journalists who cover the league.
But Gruden's behavior was not limited to 2011. Gruden exchanged emails with Allen and other men that included photos of women wearing only bikini bottoms, including one photo of two Washington team cheerleaders.
Gruden also criticized President Obama during his re-election campaign in 2012, as well as then-vice president Joe Biden, whom Gruden called a "nervous clueless p&ssy." He used similar words to describe Goodell and DeMaurice Smith, the executive director of the N.F.L. Players Association.
The league is already investigating Gruden as a result of another email he wrote to Allen in 2011 in which he used racist terms to describe Smith, who is Black.
In that email, Gruden, who is white and was working for ESPN at the time, criticized Smith's intelligence and used a racist trope to describe his face.