Jon Gruden used a racist trope to describe executive director of the NFL Players Association DeMaurice Smith in a 2011 email, the Wall Street Journal reports.
“Dumboriss Smith has lips the size of Michelin tires,” Gruden wrote in a July 2, 2011, email to then Washington general manager Bruce Allen, according to the report. Gruden then was a commentator for ESPN.
At the time, the NFL was in negotiations with Smith's NFLPA to try and end a lockout.
Gruden, now the coach of the Raiders, told the Wall Street Journal that he didn't recall writing the email but that he's "really sorry," saying he was frustrated with Smith and the NFLPA at the time.