Las Vegas Raiders coach Jon Gruden sent an email with racially insensitive language about NFL Players Association executive director DeMaurice Smith in July 2011, the Wall Street Journal reported Friday.

The email, sent to the president of the Washington Football Team as the NFL and its players were in the midst of trying to resolve a lockout, said that Smith had “lips the size of michellin tires,” the Journal reported, saying it has reviewed the email.

Gruden, who was employed at the time as the lead analyst for ESPN’s Monday Night Football, told ESPN he did not recall writing the email but apologized for the fallout.

Gruden said he spoke with the Raiders’ players Friday morning to give them a heads-up that the Journal’s report would be coming out.

“I’m transparent with my players,” Gruden told ESPN.

He also said, “That might not have been the best time of my life,” referring to the lockout. “I vented a lot. … I never felt we were getting the truth and honesty [in negotiations]. I just felt that [former NFLPA executive director] Gene Upshaw never would have let it get that far.”

“I’m ashamed I insulted D. Smith,” Gruden said, adding, “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 said he has spoken with Raiders owner Mark Davis and expects to speak with him again. He was not sure whether he would face any discipline from Davis or the NFL, which condemned Gruden’s comment in a statement Friday afternoon.

“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.”

The league is looking into the matter, with disciplinary action possible for Gruden, according to multiple reports.

Davis did not immediately respond to requests for comment from ESPN.

The email came to light during the NFL’s investigation of workplace misconduct with the Washington Football team, as “the league was informed of the existence of emails that raised issues beyond the scope of that investigation,” according to McCarthy. Senior league executives reviewed the content of more than 650,000 emails, including the one the Journal reported was written by Gruden to Bruce Allen, then the president of the Washington Football Team. The NFL had sent pertinent emails to the Raiders for review.

“This is not the first racist comment that I’ve heard and it probably will not be the last,” Smith told the Journal. “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,” 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 Associated Press contributed to this report.