One of the biggest coaches in the NFL has resigned for misogynistic and anti-gay language in emails before he was appointed coach of the Las Vegas Raiders

According to The New York Times, Jon Gruden sent emails to Bruce Allen, the then President of the Washington Football Team, and others during a seven-year period that ended in 2018.

Gruden emailed Allen that NFL Commissioner Roger Goodell should not have pressured then-Rams coach Jeff Fisher to draft “queers,” referring to a former player who was gay.

The Times also reported that Gruden used an anti-gay slur in several instances while referring to Goodell, and used offensive language to describe some owners, coaches and media members who cover the league.

Gruden also denounced the emergence of women as referees in his emails, according to The Times, and said that Eric Reid, who kneeled during the national anthem to protest racial injustice, should be fired.

He has apologised for his “insensitive remarks” and said “sorry, I never meant to hurt anyone” in a statement on Monday local time