Raiders’ timeline of 2021 drama, from Jon Gruden’s emails to Henry Ruggs’ DUI to Damon Arnette’s release

To call the Raiders’ 2021 regular season tumultuous would be an understatement. It may be one of the most drama-filled campaigns in NFL history.

Raiders fans probably thought that nothing could be worse than the Antonio Brown saga of 2019, but week after week, major issues have cropped up and team leadership has had to deal with it. Over the last month-plus, they have had to part ways with their coach, Jon Gruden, and two recent first-round draft picks, Henry Ruggs III and Damon Arnette, because of off-the-field issues.

Mike Mayock and Rich Bisaccia have done a nice job staying afloat considering all the turmoil that has come their way. But surely, the two men are hoping that things will calm down after another tumultuous week for the franchise.

Even despite this, the Raiders are sitting at 5-3 entering their “Sunday Night Football” game against the Chiefs. Frankly, it’s amazing that they’ve gotten this far and that they’ve continued to win with so many potential obstacles and distractions getting in their way.

Here’s a look back at all of the off-the-field issues that the Raiders have dealt with during the 2021 NFL season.

JON GRUDEN RESIGNS: Explaining the emails that led to him leaving the Raiders

Timeline of Raiders 2021 drama

September, 2021: The Raiders open the season with a 33-27 overtime win against the Ravens in front of their home crowd. They win twice more in the month of September to improve their overall record to an AFC-best 3-0.

Oct. 4, 2021: The Raiders suffer their first, and only, home loss of the season. The Chargers beat them 28-14 as Derek Carr records a season-low 196 passing yards.

Oct. 8, 2021: An email sent from Jon Gruden to Bruce Allen is leaked. The communication — dated July 21, 2011 — contained a racist insult of Executive Director of the National Football League Players Association, DeMaurice Smith.

“Dumboriss Smith has lips the size of michellin (sic) tires,” the email read.

Gruden claimed that the insult was not racist and that he refers to liars as having “rubber lips.”

Oct. 10, 2021: ESPN’s Chris Mortensen breaks a story revealing that Gruden admitted to calling Roger Goodell an unspecified expletive in his email exchanges with Allen during the 2011 NFL lockout.

“I was in a bad frame of mind at the time [in 2011], and I called Roger Goodell a [expletive] in one of these emails too,” Gruden said. “They were keeping players and coaches from doing what they love with a lockout. There also were a lot of things being reported publicly about the safety of the sport that I love. I was on a mission with high school football [in the Tampa, Florida, area] during that time, and there were a lot of parents who were scared about letting their kids play football. It just didn’t sit well with me.”

Oct. 10, 2021: The Raiders lose their first home game of the season 20-9 at the hands of the Bears. They put forth an uninspired effort and dropped to 3-2 on the season.

Oct. 11, 2021: The New York Times drops a bombshell story revealing comments Gruden made in his email exchanges with Allen. He used sexist, homophobic and misogynistic language in the emails and referred to Goodell as a “f–t” and a “clueless anti football p—y.” He also using homophobic language talking about other NFL owners and Michael Sam, the first openly gay player to be drafted into the NFL.

Oct. 11, 2021: Gruden resigns from his post as Raiders head coach, via a statement. 

“I have resigned as Head Coach of the Las Vegas Raiders. I love the Raiders and do not want to be a distraction. Thank you to all the players, coaches, staff, and fans of Raider Nation. I’m sorry, I never meant to hurt anyone.”

The Raiders accept Gruden’s resignation. Special teams coordinator Rich Bisaccia is named interim head coach.

Oct. 12, 2021: Keyshawn Johnson blasts Gruden, saying that his former coach has “always been a fraud.” The Buccaneers remove Gruden from their Ring of Honor, citing their “core values.”

Oct. 13, 2021: EA Sports removes Gruden as the Raiders’ coach in its popular video game Madden 22.

Oct. 13, 2021: Raiders quarterback Derek Carr comments on Gruden’s departure from the Raiders. He shows some compassion for his former coach, saying he “loves the man” but “hates the sin.”

“Don’t get me wrong, I love the man, and you hate the sin,” Carr said, via ESPN. “Like for anybody, no one is perfect. If we just started opening up everybody’s private emails and texts, people will start sweating a little bit. Hopefully not too many, but maybe that’s what they should do for all coaches and GMs and owners from now on. You got to open up everything and see what happens. But you hate the action, you hate it. You’re not supposed to like it, but you love the person. And I love the person. I’ve grown to love him so much.” 

Oct. 13, 2021: Raiders GM Mike Mayock confirms that he has been talking to Black players and Carl Nassib about their thoughts and feelings in the aftermath of Gruden’s emails and departure. Nassib, the NFL’s first openly gay player, was allowed to skip that day’s practice while dealing with the email fallout.

Oct. 14, 2021: Nassib returns to practice after his personal day.

Oct. 15, 2021: The AP reports that the NFL didn’t find other emails containing language like that exchanged between Allen and Gruden during their investigation of the Washington Football Team.

Oct. 17, 2021: Rich Bisaccia coaches the Raiders for the first time and leads them to a 34-24 win over the Broncos.

RIVERA: Who is Rich Bisaccia? Meet the Raiders’ interim head coach

Oct. 20, 2021: Raiders running back Josh Jacobs praises Bisaccia for his sideline demeanor.

“Man, the sideline … it was like [there was no] anxiety,” Jacobs said, per Adam Hill of the Las Vegas Review-Journal. “It was weird. It was like everybody was calm. You didn’t have somebody cussing at you, or going crazy at the refs. None of that.”

Oct. 21, 2021: The United States House of Representatives announces an inquiry into the NFL’s handling of its investigation into the Washington Football Team — specifically, why the league didn’t release a written report of its findings. That investigation is what led to the uncovering of Gruden’s emails.

Oct. 24, 2021: The Raiders win their second game with Bisaccia as head coach. They crush the Eagles 33-22 at home and head into the bye with a 5-2 record at first place in the AFC West.

Oct. 27, 2021: Raiders owner Mark Davis expresses to NFL owners that he would like a written report of the Washington Football Team investigation released. He also criticized the timing of the Gruden email leaks and that he wished the Raiders were made aware of them before the season began.

“I believe that if we had gotten the information earlier in the summer, when (the NFL) learned about it, it would have been a lot easier for everyone involved,” Davis said. “Then we could have done something before the season, rather than in the middle of the season.”

Nov. 2, 2021: Raiders wide receiver and 2020 first-round draft pick Henry Ruggs III is involved in a fatal car crash in Las Vegas, Nev. The crash occurred at 3:39 a.m. local time. Ruggs was charged with driving under the influence resulting in death and reckless driving after killing 23-year-old Tina Tintor and her dog. Ruggs’ Corvette was going 156 mph before the crash, during which he rear-ended Tintor’s car.

GREER: What to know about Henry Ruggs III’s fatal car crash

Nov. 2, 2021: The Raiders release Ruggs in wake of this crash and make a statement about the incident.

“Our hearts go out to the family and friends of the victim of this horrific tragedy. We will continue to gather facts and monitor the matter under our policies, but our thoughts at this time are with those impacted by this devastating incident.”

Nov. 3, 2021: Ruggs makes his first appearance in court. He is wearing a neck brace and prosecutors in Clark County, Nev., added three more charges to the case docket: DUI resulting in substantial bodily harm; reckless driving resulting in death or substantial bodily harm; and possession of a gun while under the influence. The first two counts are felonies while the third is a misdemeanor. Bail was set at $150,000.

Nov. 3, 2021: Derek Carr speaks about Ruggs’ incident. The Raiders quarterback expressed guilt about not doing enough to help Ruggs and says that Ruggs “needs to be loved.”

“I will always be there for him. That won’t change, and I’ll prove that over the course of time to him. Not to anybody else,” Carr said. “He’s probably feeling a certain type of way right now. He needs to be loved. If no one else will do it, I’ll do it.”

Carr added: “Just seeing that and getting the news when we woke up, how am I supposed to handle that? How am I supposed to react? I do sit back and I think, did I not let him know that I’d be there for him at 3 a.m.? I want to be better. Could I have been better to help? I just wish I could have done something.”

Nov. 3, 2021: Bisaccia addresses the Ruggs situation and says, “I don’t know if I can put into words the emotional feelings I went through.” The Raiders’ coach also spoke to the mood in the locker room after news of the crash broke.

“As grown men, we all have to respond in a certain way. We’re all forging our identity in life and certainly in the locker room how we deal with adversity.”

Nov. 5, 2021: Video of Raiders cornerback Damon Arnette brandishing a gun and making death threats surfaces. Arnette has been on IR since Oct. 2 with groin and thumb injuries and is facing lawsuits stemming from an offseason car crash.

MORE: Why the Raiders released Damon Arnette, explained

Nov. 7, 2021: The Raiders lose their first game under Bisaccia, 23-16 against the Giants. Carr and the team refused to blame the off-field distractions for their losing effort.

“I thought mentally we were ready,” Carr said, via the Associated Press. “Myself, I was ready to go. I was excited just to play football. I don’t think emotions or anything like that were into it. The second interception had nothing to do with emotion. That was a decision I made. It didn’t work out.”

Nov. 8, 2021: The Raiders sign veteran receiver DeSean Jackson. He adds depth and speed at receiver in wake of Ruggs’ arrest.

Nov. 8, 2021: Mike Mayock announces that the Raiders have released Damon Arnette in wake of his video release. Arnette and Ruggs were both first-round picks by the Raiders in 2020. Mayock explained the decision to release Arnette, who the Raiders had tried to help with maturity issues and character concerns.

“Very painful decision,” Mayock said, per ESPN. “We spent significant time, effort and resources trying to help him in all aspects of his life.

“There have been a series of bad decisions over the last year or so, but we can’t stand, we cannot stand for the video of Damon with a gun, threatening to take a life. The content was unacceptable, contrary to our values and our owner Mark Davis has been very clear and very consistent that this is not how we will conduct ourselves in this community. The bottom line — the Raiders will not tolerate this type of behavior.”

Nov. 12, 2021: Jon Gruden sues the NFL and commissioner Roger Goodell alleging the league “selectively leaked Gruden’s private correspondence to the Wall Street Journal and New York Times in order to harm Gruden’s reputation and force him out of his job,” Gruden’s attorney, Adam Hosmer-Henner of McDonald Carano, said in a statement.