From the second the emails came out about Jon Gruden, we knew he wasn't going to take this lying down. Then he resigned from the Raiders. Now he's back with a lawsuit against the NFL for defamation, and I sort of hope he goes to trial and wins. He's the lesser evil in this scenario.
Before you grab your torches and pitchforks, it's not so much that I want him to get the money, rather that I want the precedent there and that the NFL loses the money. Also as a massive bonus regardless of the trial outcome, all 650,000 emails get dragged into public record during discovery as part of the case. Those emails being public knowledge is what's really important. The fact that Gruden is the one being exposed for saying racist and homophobic things means there's got to be worse things hiding in there. This is more like choosing which breed of dog whose shit you're going to have to eat. Hopefully you don't want either but better to choose the German Shepherd over the Great Dane.
Gruden's case basically hinges on "I fully admit that I'm a massive piece of shit, but there are emails in there of far bigger pieces of shit than I am, and the NFL intentionally only exposed my emails and are hiding theirs. I believe that the selective exposure of information to make me look bad and not them as well is defamation. I also believe the timing of it was intentional to harm me further." I as a completely biased and jaded person totally believe that to be the case. He's just the sacrificial lamb sent out to protect others that are/were in the league who have done or been an accomplice to far worse things. The Washington Football Team scandal may be a chunk but I don't believe that's the whole iceberg. There's also Stan Kroenke vs St. Louis (another legal battle just starting up) and an ongoing feud between Mark Davis (owner of the Raiders, who Gruden was the coach of before his resignation) and the league that goes all the way back to Ray Davis (Mark's dad) in the 1970's.
Now, if the NFL were smart, they'd try to keep this out of the media as much as possible and try to settle with Gruden for way more than he could have made in the remainder of his working life ($200 million or so). After the emails came out, he's pretty much radioactive as a commentator or a coach. He was making $10 million per year as coach of the Raiders and Tony Romo is making $17 million per year as an NFL commentator now so maybe $200 million is even a bit low. They want to put this to bed before discovery, because once that happens and the emails come out, this lawsuit will be the least of their worries. A lot of dirty laundry's getting aired when that happens. They'll throw heaps of money at him to try to keep him quiet.
Gruden knows this and I think he's not out for the money. He won't take a settlement because he's out for blood. He's got well and above enough money to be set for life, and his kids, and their kids probably. He wants all those emails to come out and for them to see the light of day in court. Unless the case gets summarily dismissed, he's got them over a barrel.
This is going to be interesting to keep track of, at least until either discovery or "settled for an undisclosed sum" happens. If discovery happens, we'd best all hand onto our hats because things are going to come out (hopefully slowly if the news can restrain themselves for maximum effect) and the NFL is going to have to respond to all of it with distractions or quick fixes while hoping it doesn't affect their legal defense. The Washington Football Team tried to distract from their email controversy (which spawned this whole mess) with a half-assed Sean Taylor number retirement. Who knows what the NFL will come up with.