Las Vegas Raiders head coach Jon Gruden found himself in hot water on Friday after an email was leaked of him making a racial gesture towards NFLPA executive director DeMaurice Smith during the 2011 NFL lockout. Gruden has since apologized for his actions, via The Athletic's Vic Tafur:

Jon Gruden referred to Smith's lips as “the size of michellin tires”, playing into the old-age stereotype of black people. This was also another part of his apology:

“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.”

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This is obviously very disturbing, but Gruden is taking accountability for his actions. Smith initially responded to the comments in the report from The Wall Street Journal, making it clear that this isn't the first time he's dealt with racism:

“This is not the first racist comment that I've heard and it probably will not be the last,” Smith said of Jon Gruden. “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.”

The email was allegedly sent from Gruden to Washington GM Bruce Allen. Gruden was an employee of ESPN at the time. As for Smith, he still remains in his position with the NFLPA after 12 years, but his tenure could be coming to an end soon.

It's definitely good Jon Gruden has apologized, but you'd have to believe this will leave a sour taste in everyone's mouth across the league.