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Source: Chris Unger / Getty

Jon Gruden’s venture back into NFL coaching hasn’t gone as planned.

His coaching has slowly improved over the last four seasons, with his record going from 4-12 to starting out this season with a 3-1, but it seems some old news from a decade ago has caught up with him. As the Wall Street Journal reports, in 2011, Gruden made a racist comment about NFL Players Association executive director DeMaurice Smith, who is Black.

At the time, Gruden was a correspondent for Monday Night Football. Amidst a lockout season, he sent an email to the president of the Washington Football Team in July, which read, “Dumboriss Smith has lips the size of michellin tires.”

Once the news got out, he apologized via ESPN, saying, “I’m ashamed I insulted De Smith. 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 went on to say the term “rubber lipped” is a term he often used for people who he knows are lying but refuse to admit it, but also says that the email took it “too far.”

The NFL released a statement late Friday afternoon to denounce Gruden’s actions, with a possible punishment to follow.

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

Once Twitter users got word of Gruden’s racist comments, they immediately began to roast the Oakland Raiders coach. Check out some of the best reactions below:

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