In July 2011, current Las Vegas Raiders head coach Jon Gruden—then a color commentator for ESPN—sent an email to former Washington Football Team president Bruce Allen that used a racist trope to describe NFL Players Association executive director DeMaurice Smith.
"Dumboriss Smith has lips the size of michellin tires," he wrote, per Andrew Beaton of The Wall Street Journal.
The email was sent during a lockout by the players that summer. On the day Gruden sent the email, the NFLPA chose not to vote on a collective bargaining agreement ratified by the league's owners.