Droste, McVay, and Reader did not respond to requests for comment.
Gruden and Allen are longtime friends and colleagues. Allen was a senior executive with the Raiders from 1995 to 2003, when he worked with Gruden, who was head coach of the team from 1998 to 2001. Gruden became head coach of the Tampa Bay Buccaneers in 2002 and beat the Raiders in the Super Bowl that season. Allen became the general manager there in 2004. Allen and Gruden both left the Buccaneers after the 2008 season. While Gruden moved on to a broadcast role with ESPN, Allen became the general manager in Washington in 2010 and later the team’s president.
Allen, who is the son of legendary N.F.L. coach George Allen, and Gruden — whose father coached at Notre Dame and whose brother, Jay, was head coach in Washington from 2014 to 2019 — are part of an exclusive network that cycles between N.F.L. teams, networks and companies affiliated with the league.
In June, the N.F.L. congratulated Nassib after he became the first active N.F.L. player to publicly declare that he is gay. Goodell said he was “proud of Carl for courageously sharing his truth today. Representation matters.”
Privately, Allen and Gruden appeared to have few boundaries in expressing homophobic and transphobic language. In one email from 2015 that includes Droste, McVay and others, Gruden crudely asked Allen to tell Bryan Glazer, whose family owns the Tampa Bay Buccaneers where Gruden coached until 2008, to perform oral sex on him. Allen said Glazer would “take you up on that offer.”
Allen and Gruden also mocked Caitlyn Jenner, who received an award from ESPN in 2015 after she transitioned.
In an email from 2015, Allen and Gruden criticized a congressional bill that aimed to force the Washington franchise to change its name, which some Native Americans and others have denounced as a slur. Again using a vulgar term, Gruden took aim at Goodell and his staff even though the commissioner had initially defended the team’s right to keep the name.
In 2017, Droste shared with the group a sexist meme of a female referee to which Gruden replied, “Nice job roger.”
That same year, Gruden was sent a link to an article about N.F.L. players calling on Goodell to support their efforts promoting racial equality and criminal justice reform. Gruden had advice for Goodell:
“He needs to hide in his concussion protocol tent,” he wrote.