The NFL reportedly sent the Raiders additional past emails sent by Gruden to review after another older email sent by the coach using a racist comment in reference to NFL Players Association executive director DeMaurice Smith, who is Black, surfaced prior to Gruden's resignation

Gruden sent emails to then-Washington Football Team president Bruce Allen and others between 2011-2018, which included accusing NFL commissioner Roger Goodell of pressuring then-Rams head coach Jeff Fisher to draft "queers" in reference to the team selecting Michael Sam, an openly gay player, in 2014, The Times reported. Gruden also used an anti-gay slur on several occasions when discussing Goodell, as well as offensive language to describe some league owners, coaches and NFL media members.

Gruden also reportedly denounced the emergence of female NFL referees and called for safety Eric Reid, who took a knee during the national anthem to protest racial injustice, to be fired in the emails, according to the Times.

Gruden also reportedly responded to an article link related to NFL players seeking Commissioner Goodell's support in their ongoing effort to promote racial equality and criminal justice reform with an email stating: "He needs to hide in his concussion protocol tent."

Gruden was employed by ESPN and served as a lead analyst during the network's Monday Night Football broadcasts at the time of the emails mentioned in the Times' report.

"The comments are clearly repugnant under any circumstance," ESPN said in a statement.

Gruden's emails were brought to light amid the NFL's investigation into workplace misconduct within the Washington Football Team, with league spokesman Brian McCarthy stating, "the league was informed of the existence of emails that raised issues beyond the scope of that investigation," ESPN reported at the time.

Senior NFL executives reportedly reviewed more than 650,000 emails during the investigation, which included ones between Gruden and Allen, before the league sent relevant emails to the Raiders for review. Gruden had previously coached the Raiders from 1998 to 2001, when he was traded during the following offseason to the Tampa Bay Buccaneers, immediately leading the Bucs to their first Super Bowl title in franchise history against his former team.

Gruden was fired by Tampa Bay in 2008, joining the Monday Night Football broadcast team the following season. The 60-year-old was re-hired by the then-Oakland Raiders in 2018, agreeing to a 10-year, $100 million contract.

Coors Light Hockey Night

When: Wednesday, December 18th at 6:30pm

Where: Shakopee

What: Join Cory Cove on December 18th at Shakopee Bowl in Shakopee for Coors Light Hockey Night with KFAN! Watch Minnesota play Florida and play trivia for your chance to win a pair of Suite tickets to a Minnesota hockey game on January 9th!