Las Vegas Raiders head coach Jon Gruden used a racist trope to describe DeMaurice Smith, executive director of the National Football Players Association, during lockout negotiations in 2011, Andrew Beaton of The Wall Street Journal reported on Friday.

In an email dated July 21st, 2011, Gruden, at the time an employee of ESPN, sent an email to then Washington Redskins general manager Bruce Allen in which he compared the size of Smith's lips to car tires, playing into ages-old racist stereotypes of Black people.

“Dumboriss Smith has lips the size of michellin tires,” Gruden wrote in the email provided to The Wall Street Journal.

Gruden told The Journal that while he doesn't remember writing the specific email in question, he's still “really sorry.” He expressed his frustration at the time with terms of the lockout, insisting he was “upset” and “used a horrible way of explaining it.”

“I don’t think he’s dumb. I don’t think he’s a liar,” Gruden told The Journal of Smith. “I don’t have a racial bone in my body, and I’ve proven that for 58 years.”

The NFL released a statement Friday decrying Gruden's email.

Smith, 57, was unanimously elected to head up the NFLA in 2009. His 12-year tenure could soon be coming to an end, though, after the NFLPA's executive committee failed to reach unanimous consent on retaining him. The union will reach a final decision on Smith's future soon.

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In a statement to The Journal, Smith condemned Gruden's comments, noting that they're hardly the first racist remarks he's heard in his position of power “in corporate America.”

“Racism like this comes from the fact that I’m at the same table as they are and they don’t think someone who looks like me belongs,” Smith said. “I’m sorry my family has to see something like this but I would rather they know. I will not let it define me.”

The Raiders, 3-1, host the Chicago Bears in Las Vegas on Sunday.