This month's email leaks weren't the first time in recent years Jon Gruden has been in trouble. Last year, the Las Vegas Raiders accumulated over $1 million worth of fines due to multiple violations of the NFL's COVID-19 protocols, including one instance where the coach wasn't properly wearing his face mask, per CBS Sports. However, it's still hard to top what The New York Times just uncovered, never mind the fact that Gruden's email exchanges with former Washington Football Team president Bruce Allen, among others, took place years ago.

According to the publication, Gruden targeted several individuals in the emails, not the least of these being longtime NFL commissioner Roger Goodell, whom he referred to as a "clueless anti-football p***y" and a "f***ot." Apparently, the coach wasn't happy with Goodell's efforts to make the NFL safer and reduce the risk of concussions. He also called out the then-St. Louis Rams for making Michael Sam the first openly gay player to be picked in the NFL draft; according to Gruden, the team shouldn't have been pressured into drafting "queers." Additionally, he called for the firing of former San Francisco 49ers and Carolina Panthers safety Eric Reid for his national anthem protests and dished out several insults at journalists, owners, and coaches, the Times added.

In another email to Allen, Gruden reportedly wrote that NFLPA president DeMaurice Smith "has lips the size of michellin [sic] tires," though he told subscription-only site The Athletic this month that he felt he had gone too far and was "really upset" about the possibility of a lockout shortening or canceling the 2011 NFL season.