As someone who loved Nate in 2012 and 2008, I figure it's worth a quick discussion on why I've soured on him so much this cycle. I think a lot of people adopt a sort of natural reaction of "he just isn't pro Hillary enough that's why GAF hates him", but the guy has been more or less a disaster ever since he left the Times, and I've hated the new 538 long before we headed into the general.
I do want to say though that I think Silver deserves a lot of credit. He popularized out of sample demographic regressions and poll averaging and brought a lot of rigor to election prognostication which wasn't there before. It's hard to overstate how astonishingly shitty election analysis was in 2004. Silver upped everyone's game. His biggest problem is that he's no longer competing in the same pundit environment as 2008. That, and his fickle contrarian streak has been hurting him. His competitors are just much better than him at this point, and Silver hasn't been able to keep up.
The first red flags were in the run up to the launch of 538, where Silver aspired to discuss economics and education and god knows what else in addition to sports and politics. Of course, Silver was successful in politics and sports because he had much better data skills than the average sports writer or political hack. Somehow, success there convinced him that as someone with no advanced degrees, he could move into turf held by people who've dedicated their careers to quantitative causal analysis and enjoy a similar disruption. It was a disastrous plan from the word go, and the launch of 538 and wealth of insipid econ articles confirmed it.
Making matter worse is that rather than take the criticism and work to up his game, he picked petty, stupid, self-defeating fights with Krugman and the Times. And from there it just kept getting worse.
Trump was another disaster. I don't blame Silver for not calling Trump right away, or for relying on an endorsement model which didn't work out. Trump was, after all, strange. But, Silver got a lot of justified criticism for being aggressively defensive, adopting a lot of lazy, superficial defenses, and for just refusing to think critically about the election for a solid 6-8 months. His go to defense was an allusion to Herman Cain which was just a silly comparison on any level. He never engaged in serious thought about the size or persistence of Trump's lead, Trump's geographical strength, the trendlines of his favorables, or polling which accurately predicted that there was never going to be some kind of magical anti-Trump consolidation. Silver was just completely non-serious about the election for months, and repeatedly got antagonistic and more stubborn about it as his position became more untenable.
As far as the general this year, I think the nowcast is transparent click-bait, and I think that Silver's writing is motivated by contrarianism in a way that's unhelpful to anyone. Just this week, Wolfers politely asked him to explain some anomolous results and Silver's only reaction was to call him lazy and pick a fight.
A lot of people have pointed out in this thread that the model does weird stuff sometimes. And sure, it does. But I mean, whatever. That in and of itself isn't the problem. The problem is that poll averaging is actually quite easy, he's competing with more academics than he used to, and he simply doesn't have the training or background to add value to the discussion any more. Reviewing that discussion of the assumptions going into his model is just painful, because the reality is that none of these things even have to be assumed - all of those points can be structurally identified by the data. But, his model is an outlier and it does weird things because while Silver legit doesn't know how to make it better, but he still has to do something, because his original contributions are no longer special or interesting. Election coverage has internalized the main points and moved on.
Like I said, Silver was a big, big deal in 2008 and belongs in the political writing hall of fame, because he really changed the game. But, it's not the same game any more. He's not a great editor(nor does he have one), he never went to grad school, and the game he created has left him behind. Such is life - these things happen. But he's not content to be left behind, so rather than continue as one part of a larger discussion and search for a new contribution, he just picks shitty fights on twitter and spends most his time looking like an idiot.
I guess another way of saying all of this is that ESPN was a mistake. As the electoral-vote dude pointed out, when you're part of an academic or news-gathering ecosystem, there's a certain amount of space that comes with the territory that helps. Silver doesn't have that, he needs it, and it shows. It has been a long, ugly fall for him.