This was in an era when some still thought that the Windows phone could be a viable alternative to Android and the iPhone. Instagram was less than a year old and Twitter wasn't nearly that platform that it is now. No one knew that Facebook was the evil empire. People would say things like "The internet never forgets" but no one really knew what that meant.

In that era, when high-schoolers and college students were commonly using the "homophobic" slurs that Gruden used, it really wasn't foreseeable that, in the near future, 1) those slurs would make someone a pariah and 2) that those emails would be accessible and easily searchable by 3rd parties looking for dirt.

In 2021, it's absolutely the case that we can expect people to be very careful about what they post online, but we only developed that wisdom after 2011.