On July 21, 2011, the National Football League and its players were working to resolve a lockout that threatened the upcoming season. That day, the league’s owners voted to ratify a new collective bargaining agreement—but the players opted not to vote on it immediately, citing outstanding issues that the union was fighting to resolve. 

That same day, Jon Gruden—the current Las Vegas Raiders coach who has been one of the most prominent figures in the NFL over the past two decades—sent an email about DeMaurice Smith, the executive...

On July 21, 2011, the National Football League and its players were working to resolve a lockout that threatened the upcoming season. That day, the league’s owners voted to ratify a new collective bargaining agreement—but the players opted not to vote on it immediately, citing outstanding issues that the union was fighting to resolve. 

That same day, Jon Gruden—the current Las Vegas Raiders coach who has been one of the most prominent figures in the NFL over the past two decades—sent an email about DeMaurice Smith, the executive director of the NFL Players Association, to a team executive. Gruden’s email described Smith with a racist trope common in anti-Black imagery. 

“Dumboriss Smith has lips the size of michellin tires,” he wrote in the email reviewed by The Wall Street Journal. 

Gruden is currently the head coach of the Las Vegas Raiders, having previously coached both the Raiders and the Tampa Bay Buccaneers, the franchise he led to its first Super Bowl win after the 2002 season. He was a broadcaster for ESPN at the time he sent the email to Bruce Allen, who was then the president of the franchise now called the Washington Football Team. 

In an interview, Gruden said he can’t specifically recall writing the email but apologized for using that language. 

“I’m really sorry,” he said. 

The NFL is reviewing Gruden’s status with the Raiders for potential discipline, a person familiar with the matter said. 

Gruden said he had been angry at the time because of the lockout and didn’t trust the direction the players, led by Smith, were going in the negotiations. He said he has in the past referred to people he believes to be lying as “rubber lips” and that he took it “too far.”   

“I was upset,” Gruden said. “I used a horrible way of explaining it.” 

“I don’t think he’s dumb. I don’t think he’s a liar,” Gruden said. “I don’t have a racial bone in my body, and I’ve proven that for 58 years.” 

In a statement to The Wall Street Journal, Smith said Gruden’s comments reflect the difficult reality Black people continue to face as they advance their careers.

“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,” Smith said. “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.”

‘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,’ DeMaurice Smith said.

Photo: Perry Knotts/Associated Press

The NFL said, during the course of the investigation into workplace misconduct at the Washington Football Team that finished this summer, it was “informed of the existence of emails that raised issues beyond the scope of that investigation.”

Over the past few months, the NFL said, senior NFL executives have reviewed more than 650,000 emails, including this one, at commissioner Roger Goodell ‘s direction. Earlier this week, the executives presented a summary of that review to Goodell. The league added that it is sharing emails pertaining to Gruden with the Raiders. 

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

Raiders owner Mark Davis, in a Friday evening statement after this story’s publication, said the content of the email is “disturbing and not what the Raiders stand for.” 

“We were first made aware of the email late yesterday by a reporter and are reviewing it along with other materials provided to us today by the NFL,” the statement said. “We are addressing the matter with Coach Gruden and will have no further comment at this time.” 

A review of other emails in the same thread did not make it clear what prompted Gruden’s comment. The email chain initially began with several people discussing a TMZ story about Tiger Woods splitting with his longtime caddie. The discussion then shifted to NFL matters, although the context of the remarks was not clear. 

Allen did not respond through multiple attempts to reach him. 

Gruden, 58 years old, has long been one of the biggest coaching stars in football. He was hired to coach the then-Oakland Raiders beginning in 1998 after he was seen as one of the brightest young offensive assistant coaches in the sport. In 2002, he became the coach of the Buccaneers as part of an unusual trade in which Tampa Bay gave up numerous draft picks and millions of dollars to acquire him. During his first season with the Buccaneers, he became the youngest coach at the time to win a Super Bowl, in a victory over his former team, the Raiders. 

Jon Gruden, right, with then-Washington Redskins president Bruce Allen, left before a preseason football game in 2017.

Photo: AP

Gruden never replicated that success and after seven seasons with the team, following the 2008 season, he was fired. Afterward, he became a high-profile broadcaster on ESPN, calling Monday Night Football games.

The Raiders brought him back in 2018 with a lucrative deal to become their coach again. The team, which moved to Las Vegas last year, failed to reach the playoffs during his first three years back with the club. So far this year, it is 3-1, tied for first place in the division. 

Smith, 57 years old, has been the NFLPA’s executive director since 2009. In 2011, when Gruden sent the email, Smith led the players through contentious labor negotiations with the NFL that resulted in a lockout lasting for more than four months. 

After the NFL owners approved the new deal, the settlement was approved and ratified by the players in the ensuing days after further negotiations. The agreement included a number of improvements for players, including more benefits for retired players, a new salary floor and more guaranteed injury-protection money. 

Smith was also at the helm for the most recent bargaining negotiations that produced a new, decade-long deal in 2020. That agreement paved the way for the league’s lucrative new round of media deals, valued at more than $100 billion, and the NFL’s new 17-game season, which the players agreed to in exchange for a larger share of the revenue. 

That latest deal, which was finished just as the Covid-19 pandemic was first disrupting sports in the U.S., only passed with a narrow approval of the players, however. Smith’s long-term future is currently being decided by player leadership, with his contract expiring in 2022. 

Write to Andrew Beaton at andrew.beaton@wsj.com