Raiders Coach’s Emails Included Homophobic and Misogynistic Comments

When the vaunted N.F.L. coach Jon Gruden was confronted with a racist email he had sent in 2011 to insult the head of the players’ union, he said he went too far but didn’t have “a blade of racism” in him.

But league officials as part of a separate workplace misconduct investigation that did not directly involve him have found that Gruden, now the coach of the Las Vegas Raiders, casually and frequently unleashed misogynistic and homophobic language over several years to denigrate people around the game and to mock some of the league’s momentous changes.

He denounced the emergence of women as referees, the drafting of a gay player and the tolerance of players protesting during the playing of…