USA Today

Jon Gruden has apologized for comments he reportedly made about NFLPA executive director DeMaurice Smith in a 2011 email sent to then-Washington Football Team president Bruce Allen in 2011. The email was sent as the league and the NFLPA were in the process of trying to end a lockout. 

In the email, Gruden said that Smith had "lips the size of a michellin tires," according to a report from The Wall Street Journal. The email was discovered during the league's investigation of workplace misconduct with the Washington Football Team. The NFL told the Journal that is has reviewed 650,000 emails during its investigation. The league has sent pertinent emails for the Raiders to review. 

The Raiders issued a statement regarding the email and are continuing their investigation.

While he said that he did not specifically recall writing that email, Gruden said he is "really, really sorry" for his criticism of Smith. Gruden told ESPN that he has used the term "rubber lips" to "refer to a guy I catch as lying ... he can't spit it out." Gruden said that he has spoken about the matter with Raiders owner Mark Davis and expects to speak with him again. Gruden added that he hopes he does not face discipline from Davis or the league. 

"I'm ashamed I insulted De Smith," Gruden said. "I never had a racial thought when I used it. ... I'm embarrassed by what's out there. I certainly never meant for it to sound that bad."

Gruden told the Journal that his comments about Smith came out of frustration with Smith and the lockout. 

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

The NFL issued a statement regarding Gruden's comments. 

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

The NFLPA executive director for the past 12 years, Smith responded to Gruden's comments via the Journal. 

"This is not the first racist comment that I've heard and it probably will not be the last," Smith said. "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."

On Friday night, NFLPA team representatives voted to retain Smith in his role. Smith received the minimum number of 22 votes for another term.