Las Vegas Raiders coach Jon Gruden is resigning after repeatedly using homophobic and misogynistic language in emails sent over a period of seven years and obtained by the NFL as part of an unrelated investigation, according to a report in The New York Times on Monday. The Times reported Gruden used a homophobic slur to describe NFL commissioner Roger Goodell, denigrated the drafting of a gay player, mocked transgender woman Caitlyn Jenner and suggested that a player who kneeled during the national anthem should be fired, among other things. The revelations come days after The Wall Street Journal reported that, in one 2011 email, Gruden used a racist trope when describing NFL Players' Association executive director DeMaurice Smith. Gruden's emails were sent between 2011 and 2018, when he was working as a broadcaster for ESPN. They were obtained as part of an unrelated investigation into the culture of the Washington Football Team – an investigation which resulted in a fine, but for which no written report has been released.