Raiders coach Jon Gruden used a racist stereotype to refer to NFL union boss DeMaurice Smith in 2011, according to a recently discovered email.

“Dumboriss Smith has lips the size of michellin tires,” Gruden wrote during the NFL lockout in an email to Bruce Allen, then the GM in Washington.

The email was reported by the Wall Street Journal on Friday; the NFL’s first investigation of the Washington Football Team’s sexual harassment scandals uncovered emails “beyond the scope of that investigation.”

Gruden apologized,