Jon Gruden's disparaging emails were apparently not limited to DeMaurice Smith. Robert Hanashiro-USA TODAY Sports

Old emails Jon Gruden sent to former Washington Football Team executive Bruce Allen (and others) have been publicly exposed, and they have proven to be problematic for the Las Vegas Raiders head coach.

The emails Gruden sent came from the 2011-2018 time period. The emails were uncovered during the NFL’s investigation into the Washington Football Team regarding the franchise’s workplace environment. According to the New York Times, the league completed its investigation and sent commissioner Roger Goodell a summary of findings last week.

One email in which Gruden remarked about NFLPA executive director DeMaurice Smith having Michelin tire lips made headlines on Friday. The email was described as Gruden using a racist trope against Smith, although the coach disputed that and said he was calling Smith a liar.

On Monday night, ESPN’s Adam Schefter reported that the NFL sent more “damaging” emails sent by Gruden to the Raiders for them to review. The New York Times later revealed the contents of the emails.

According to the New York Times, Gruden used problematic language regarding gay people.

From the Times’ story:

In the emails, Gruden called the league’s commissioner, Roger Goodell, a “faggot” and a “clueless anti football p---y” and said that Goodell should not have pressured Jeff Fisher, then the coach of the Rams, to draft “queers,” a reference to Michael Sam, a gay player chosen by the team in 2014.

There is more.

The Times says “Gruden exchanged emails with Allen and other men that included photos of women wearing only bikini bottoms, including one photo of two Washington team cheerleaders.”

Gruden also was critical of Eric Reid for kneeling for the national anthem and called out Goodell with disparaging language, the report says. You can read the entire story here.

Gruden was in his second stint as head coach of the Raiders. The Raiders are currently 3-2. The 58-year-old won a Super Bowl as head coach of the Tampa Bay Buccaneers in the 2002 season.

More must-reads:

TODAY'S BEST
MLB announces punishment for Astros' Ronel Blanco over foreign substance
Athletics place lefty on 15-day IL, transfer infielder to 60-day
Rafael Nadal switches gears, gives major update on French Open status
Atlanta to be first race of NASCAR's In-Season Tournament
West Point alum made history in his MLB debut with Reds
Heat legend cautions Lakers against hiring JJ Redick
Welcome to the WNBA: Caitlin Clark sets infamous record in debut
Jalen Brunson leads Knicks to blowout win in Game 5 vs. Pacers
Nikola Jokic torches DPOY to lead Nuggets past Wolves in Game 5
Oilers use late heroics to tie Canucks at two games each
Watch: Astros pitcher ejected after foreign substance check
Kirk Cousins not angry with Falcons because winning is 'hard enough'
Bronny James has surprising comments on potentially teaming up with LeBron
Bills add two-time Super Bowl champ to new-look WR room
Brewers lose team-leading home run hitter to injured list
Sandy Alderson denies involvement in Mets, Billy Eppler IL controversy
Twins reliever shut down for six weeks with patellar tendon tear
Chris Finch throws shade at Nuggets star over Rudy Gobert’s fine
Cardinals head coach warns not to bet against Kyler Murray
Details emerge on Jason Kelce’s role at ESPN

Want more sports news?

Join the hundreds of thousands of fans who start their day with Yardbarker's Morning Bark, the best newsletter in sports.