Jon Gruden apologizes after racist email toward NFLPA head leaks By  Jeremy Layton October 8, 2021 5:14pm   Updated   Las Vegas Raiders head coach Jon Gruden apologized Friday after a leaked email from 2011 came to light in which he referred to NFLPA head DeMaurice Smith using a racial stereotype. According to a report in the Wall Street Journal, Gruden sent the email during the 2011 NFL lockout to Bruce Allen, who was the GM