It has been almost four years since Jon Gruden controversially resigned from being the head coach of the Las Vegas Raiders.
But NFL star defensive end Maxx Crosby, who just signed a lucrative contract extension with the team, hasn’t forgotten the day when everything transpired.
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A report emerged back in November 2021 detailing that Gruden had used racist, misogynistic and anti-gay language in emails spanning over the course of a decade.
He was essentially pushed out the door of the Raiders’ facility as a result, ultimately choosing to resign before he was inevitably fired.
At the time, Gruden was three years into his second tenure with the Raiders, having coached them from 1998-2001, before being traded to the Tampa Bay Buccaneers in 2002.
He led Tampa to a Super Bowl XXXVII victory in his first season with the team, defeating none other than the Raiders to lift the Lombardi Trophy with a comfortable 48-21 win.
Then 39-years-old, Gruden was the youngest head coach in NFL history to win the Super Bowl, though that has since been broken by Sean McVay, who marched the Los Angeles Rams to victory in Super Bowl LVI at the age of 36.
In his second tenure with the team, Gruden was expected to be with the Raiders for the long haul, having agreed to a 10-year, $100-plus million contract in 2018.
At the time of his dismissal as head coach, Gruden had a 117-112 winning record, and was 5-4 in the playoffs.
Featuring on an episode of Glory Daze, former Cleveland Browns quarterback Johnny Manziel’s podcast, star defensive end Crosby recalled the lead-up to the report on Gruden’s behaviour behind the keyboard being publicized.
There, he spoke of how ‘sick’ he felt for his former head coach likely not being able to coach in the NFL again.
“It makes me sick for him [Gruden],” said Crosby.
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“The dude is addicted to football. He is a football lifer. Gruden was so good to me, and when that situation happened, I remember it so vividly. We started the year so well, we beat Baltimore in OT, we went to Pittsburgh, we beat Pittsburgh… we were feeling really good. We are cooking, we are feeling great.
“Going into the week we were playing Chicago, that is where the email leaked … it became a big thing. And you can tell that Gruden was … up over it. And he felt so bad and he apologized in front of the team, and he was in tears. He is like, ‘I am sorry, this is not me, this is ten years ago.’ “
“Then after the game against Chicago, that is when all the emails started leaking. And it just got worse and worse, and it was just happening so fast. And as a team, we are like, ‘What is going on?’ It is everywhere … That night, I got a call from [Mike] Mayock, and Gruden resigned.”
Shortly after his resignation, Crosby further detailed to Manziel how he and his wife Rachel visited Gruden at his home, and how they were all torn up over the situation, and would no longer be working together.
“I went to Gruden’s house right after it happened. Me and Rachel went to his house. He resigned. He’s got this beautiful f****** house, he’s just sitting in the corner like the Godfather and you could just see it. He couldn’t even look me in the eyes, bro. He was just f***** up, tearing up, bro.
“And I’m sitting there with Rachel, like me and her were both f***** up, we were all tore up, and he was just like apologizing. ‘I’m so sorry, I’m so sorry.’ I’m like, ‘coach, stop f****** apologizing, I love you to death, like you’re the one that gave me a shot when nobody else did. And like, the guys still, after all this s***, like, we still love him.
“So it was just tough to see a guy like that, who’s such a good dude and such a f****** loyal ride or die person, they went after him. They went after him, and he knew it. He said it there, and he’s like ‘I’ll be back’. To this day, he’s like that, ‘I’ll be back’.”
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The bond the two shared was certainly special, with Crosby sending his former coach a surprise gift full of Raiders gear, a gesture which made the 61-year-old deeply emotional.
Gruden joined Barstool Sports in November 2024, and is now a regular on their various NFL shows and platforms, where he has his own show titled ‘Gruden’s QB Class.’
As for Crosby, who has recently marked five years of sobriety, he has had four head coaches since Gruden’s departure from the team, who have a combined losing record of 25-38.
Now, the franchise cornerstone will be entering the 2025 season under his fifth head coach in almost as many years, as longtime Seattle Seahawks coach Pete Carroll has taken over the reins with the clear goal of helping the Raiders climb out of what has been a number of years of mediocrity.
Despite constant personnel changes among the coaching staff in recent years, the 27-year-old has demonstrated his commitment to Carroll and the entire Raiders organization by committing to a three-year, $106.5 million extension, $91.5 million of which is guaranteed.
This makes him one of the highest-paid non-quarterbacks in the league, ranking fourth overall behind Ja’Marr Chase, Myles Garrett and Danielle Hunter in terms of annual average salary, with the star DE set to command $35.5 million in the 2025 season alone.
The mission for Crosby and the Raiders in 2025 is clear – better last season’s woeful 4-13 record, and put themselves in a position to be able to reach the post-season for the first time since 2021.
Sounds simple, but the execution may prove to be much harder.