Mike Florio may think the NFL digging into Jon Gruden's emails will reveal derogatory comments when he was Raiders HC

Almost a year removed from Jon Gruden's firing, people are still talking about his emails. Derogatory and homophobic emails got the head coach fired midway through the 2021 season. However, those defending the head coach have held onto the fact that it has been a long time since the emails were sent.

That said, one NFL analyst has claimed that the league is investigating the Raiders' email servers and expects more recent emails to be found dating back to after he joined the team.

Here's what Mike Florio had to say on Pro Football Talk:

"Now, in the order proposed by Gruden's camp, they say that the emails were sent between 2011 and 2018 [before he was hired]. But the NFL has written that there were emails sent by [the head coach] after he returned to be the coach of the Raiders."

He continued, claiming the league is going to dig deep into the Raiders' servers:

"[The NFL is] going to look for anything they can. At some point, somebody decided 'why don't we go look at all the emails that [he] sent on a Raiders server and let's see if we can find some more inappropriate emails.'"

Florio also pointed out that the court filings could reveal that Gruden used derogatory comments while he was a member of the Raiders.

"This is the first shot in that battle, and the suggestion that was made by the league in the court filings last week is that there will be more evidence of consistent derogatory emails sent by Gruden not in 2011 when he wasn't working for any NFL team, but after he returned as coach of the Raiders..."

He concluded that the findings will continue to sully the head coach's reputation:

"It's just more mud that's eventually going to be thrown at Jon Gruden is going to make him look even worse."

Jon Gruden's time with the Raiders

Oakland Raiders v Seattle Seahawks

Jon Gruden was originally hired to head a long-term rebuild of the franchise. His original deal was to last 10 years and during that time, the team was going to rebuild the foundation and fix long-term problems with the organization. In his first year with the team in 2018, they went 4-12.

In his second year, they went 7-9 and in his third year, they went 8-8. Heading into 2021, something had to give. Between the change to an odd number of games and the slow but steady rise in wins, 2021 was going to be the year the team would either sink or swim.

In other words, they were expected to either continue building and inch past the .500 record regress back to the mean. Instead, the head coach was fired and the team made the playoffs on the back of a 10-7 season.

This year, the team hopes to keep the momentum going with the addition of Davante Adams and Josh McDaniels.