The digression started when I made a comment about Randy Moss' reaction to Gruden. Moss was not the target of Gruden's emails, but was obviously and honestly hurt that someone in a position of power like that, someone who controlled the fate of hundreds of black athletes over the years, would write an email like that. Maybe it wasn't the right jumping off point since as you note Gruden's comments aren't borderline, but at the time it looked like he might survive this, based on his bullshit statement that he didn't mean it that way, and the classic circling of the wagons that happens in these cases by his former colleagues in broadcasting along with former players. I used Moss' reaction as a jumping off point to discuss how even if you bought Gruden's "I didn't mean it that way" explanation, it doesn't matter as it relates to how Moss was processing the situation and his reaction to it.It is odd that we’re having these digressions about borderline use cases like “grandfathering” when the stuff Gruden wrote was racist as can be. This isn’t even a context of its time issue, shit like that was racist in 1950. And it was used with racist intent, to address the other digression.
The only surprise here is that Gruden anticipated that these would be private and he was absolutely wrong to have that expectation. I mean, it doesn’t even matter because if you say that kind of stupid shit you should be prepared to face consequences.
The only other thing I would note is that this is SOSH where we pretty much all agree this case is gross and not borderline, but if you hop on over to any number of other sports message boards out there, there are plenty of people who think Gruden was wronged here for whatever reason (they were private emails, they were 10 years ago, everyone needs to stop being so sensitive and "woke"). In that context I still think it was a worthwhile digression, "grandfathering" may be a borderline use case now, but so was the use of the "b" word or the "c" word to refer to women on this very message board during my time here. The definition of what is borderline and what is over the line is constantly moving, and as a cis white male I feel like I have an obligation to avoid the reflexive "that's ridiculous, I use that phrase all the time" reaction in these conversations.