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Why did the Jon Gruden situation come to a head when it did?

Ryan Harris joins Michael Holley and Michael Smith to explain why Jon Gruden made "one of the biggest sins in football" as a coach and how he could've potentially saved his job if he approached it differently.

Jon Gruden got what he deserved, there’s no question about that. However, did he deserve to get what he got at the specific moment that he got it?

More importantly, did the Raiders deserve to have to endure the Gruden controversy during football season?

It’s a fair question. It’s an important question. The timing of the decision to alert the Raiders to the Gruden situation and, quite possibly (if not probably), to pressure the Raiders to fire Gruden or force him to quit created a serious and significant competitive issue for the Raiders and, in turn, for multiple other teams.

In hindsight, it’s appropriate to wonder whether and to what extent the situation impeded the team’s ability to prepare for and to compete with the Bears. That obviously impacted the Raiders’ ability to move from 3-1 to 4-1. It also helped the Bears move from 2-2 to 3-2; if the Bears make it into the playoffs thanks to that one extra win that could/should have been a loss, that helps them and hurts whichever team ends up as the No. 8 seed in the NFC.

At some point during an investigation that began in July 2020 and that resulted in punishment being announced on July 1, 2021, Beth Wilkinson’s team discovered the Gruden emails. So when did the Gruden emails first surface, and what happened next?

Anyone conducting a reasonable reading of the emails would believe that they required serious consideration and action, up to and including termination of employment. For how long did Wilkinson and, in turn, the league sit on them before moving early in the week of October 3 to present the Gruden emails to the Raiders?

The league has said that it became “informed of the existence of emails that raised issues beyond the scope of the investigation” during the investigation itself. Then, “over the past few months,” a group of senior NFL executives reviewed more than 650,000 emails including the Gruden emails.

Although some think that the issue first became flagged by the reporting of the email using a racist trope in reference to DeMaurice Smith on Friday, October 8, the league acknowledges that, early in the week of October 4, the senior executives who reviewed the 650,000 emails presented a summary of the review to the Commissioner. The league then decided to share the emails with the Raiders.

To be clear, the league -- not the Wall Street Journal -- pulled the lawnmower cord during the week of October 4. Along the way, someone leaked the email regarding Smith to the Wall Street Journal. Even without the leak, the Raiders were getting the emails.

So why did the Raiders get emails about which the league had known for months during the regular season? If this had come to a head in, January, owner Mark Davis could have hired a new coach who would have spent the offseason preparing to move forward. If the league had waited until after the current season ended, Davis could have replaced Gruden then. Instead, the delivery of the emails to the Raiders -- coupled with the making of just enough of them public -- forced the team’s hand.

During a season. Let that sink in. Per a source with knowledge of the timeline, Washington owner Daniel Snyder went to the league office at some point in June to have, essentially, a hearing regarding the punishment he’d receive. Present for the hearing were the Commissioner and a small handful of owners. By the time that meeting happened, the league (we’re told) definitely was aware of the Gruden emails.

Again, why wait until October to act on the emails? Even if this had all blown up in June, Davis and the Raiders would have had time to make a hire and to get someone up to speed. The unanswered question, and it’s a critical one, is when the league first knew about the Gruden emails and why the league waited until the week of October 3 to start this process.

That’s not a defense of Gruden. It would have been wrong to let him finish the season, knowing what we now know. But it was wrong to let him even start the season, given that the league already knew.

We don’t expect to get a straight answer, or any answer for that matter, to this question. There’s really no good answer that can be provided. Still, if the league knew about these emails at or before the commencement of the usual offseason hiring process, the Raiders would have been in much better shape than they now are, scrambling to hold it together with an interim head coach and dealing with the aftermath of a tumultuous 72-hour period that started with one email being leaked and ended with Gruden walking away for good.