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. 

"I'm really sorry," Gruden told Beaton regarding the email, telling him he didn't recall sending it.  

Gruden, 58, added that he was displeased with the direction that Smith had taken the NFLPA during the lockout and had used the term "rubber lips" to describe people he thought were liars in the past, though he added that his email went "too far."

"I was upset," he said. "I used a horrible way of explaining it."

"I don't think he's dumb. I don't think he's a liar," he added. "I don't have a racial bone in my body, and I've proven that for 58 years." 

Vic Tafur @VicTafur

Jon Gruden discussed the article with his players this morning. Here are his comments to me on the offensive email: <a href="">

On Friday, Smith, 57, commented on the email:

"This is not the first racist comment that I've heard and it probably will not be the last. This is a thick skin job for someone with dark skin, just like it always has been for many people who look like me and work in corporate America. You know people are sometimes saying things behind your back that are racist just like you see people talk and write about you using thinly coded and racist language.

"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. 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 released the following statement:

Las Vegas Raiders @Raiders

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The NFL—which uncovered the email during its investigation into the Washington Football Team's toxic workplace culture—is reviewing the situation for potential disciplinary action.

"The email from Jon Gruden denigrating DeMaurice Smith is appalling, abhorrent and wholly contrary to the NFL's values," the league said in a statement. "We condemn the statement and regret any harm that its publication may inflict on Mr. Smith or anyone else."