I think Kessler's brief is fantastic.
I don't know how many brief writing seminars I've had to sit through where some blowhard (including the blowhard next to me in the front of the room when I've taught some) about how there's no place for being strident, or adjectives, or italics in briefs. It strikes me as the same sensibility that leads the same guys to pontificate that "no point worth making should take more than a page," or who teach young writers never to write a sentence longer than four lines, or never to use semi-colons, or whatever. One size fits all models simply don't work.
There are times when stridency is necessary. In moderation, almost always, but necessary. If what the other side has done is shitty, sometimes you have to call it that way, and if what they have done would make a reasonable person angry, sometimes you have to show your anger. Judges rarely admit this, but in a case where they have to decide which side is in the right and which is in the wrong, the conviction with which the side claiming an injustice presents its case is something the judge is paying attention to. If you're accusing someone of conscious bias, and railroading your client, a reasonable person would be a bit angry about it, and (and I know many lawyers disagree with this, but I feel strongly about it) showing anger is not a negative. Whether they pretend to be annoyed or not, it can be quite effective. Kessler played it close to the vest in his first brief. But now he's taking a shot directly at the king, and to dance around it in the last brief you're going to get would make no sense. The judge needs to decide whether he believes what Kessler is saying about this being a league hatchet job is true. If it is true, it's something that would make Kessler and Brady very very angry. Showing a little of that anger -- most of which is reserved for the final pages of the brief -- is not a problem.
One other thing he's done masterfully is to turn around the "generally aware" issue. Let's really deconstruct what he's done here. His argument has a problem. It is that Goodell fixed the weak "general awareness" finding by beefing it up. Where the NFL should want to fight this battle is on the question whether the decision really gives a new basis for punishment as opposed to simply finding more evidence to support the essentially same basis for punishment. But the league overshot a bit -- it made a good argument that this is not a Peterson-style change of basis for punishment, but then it tried to tack on an argument that courts don't get to consider the law of the shop. And in this brief, Kessler has used that to completely change the battlefield, making it so that this argument -- which the league is weak on -- is the only argument. He's set it up to try to persuade the judge that so long as it decides arbitral precedent is not the same as law of the shop (which is an argument for which he has Supreme Court law on his side), that his side should win.
I don't think Kessler has made a material misstep yet -- maybe my only quibble is stating as though it's a fact that the NFL leaked the "destroyed phone" angle to Stephen A. Smith. (While that's a fair inference and maybe the only reasonable inference, in the end claiming to know something you cannot know for sure can hurt credibility.) His concession at the hearing about Brady's regret about destroying the phone, was masterful. He took the hardest fact, and he disarmed it, conceded it was a problem, and then said in essence, "but let's talk about the facts now," and the judge seems to at least be following along. Kessler knows his audience. He wouldn't have written this brief this way if he didn't think it might work. Brady may not win here. Overcoming an arbitration award is hard. But I feel as though Kessler is doing what he can to give his client(s) the best chance possible.