As for the early, subjective post about the odds, that was posted on 27 August 2009, just days after Ted Kennedy died, long before there was any concrete information about who would run even for the primaries, and before there was any concrete information about the electoral influence of the tea party movement. And Nate Silver was still probably right that Romney wouldn't have been able to take Kennedy's seat, since Romney wouldn't have attracted as many of the Tea Party voters.
You also apparently didn't read his post I mentioned. It does not talk about just Romney. Here is the direct quote: "As for other Republicans in Massachusetts, their prospects don't figure to be much better."
Silver's whole failed business was based on what Taleb called the "Ludic fallacy" in The Black Swan.
Silver doesn't make "predictions", he gives odds. Giving odds implicitly admits that there exists a chance of beating those odds, and attempts to quantify how big or small that chance is. Sure, improbable things happen. That does not make them not improbable. Really, if someone is giving probabilities, you don't just count how many times the lower-probability events happened against him, you take all of his 20% probabilities and look to see whether about 20% of them ended up happening.
Look at it the other way--if all of Nate Silver's "predictions" came true, he'd be way more wrong than if some of them didn't come true, because he's not predicting things with 100% probability! Of all the things he thinks are 70% likely to happen, he's just as wrong if 100% of them happen as if 40% of them happen--he's only right if 70% of his 70% shots happen!
But you're going to have to do better than pounce on my word choice if you want to prove your point.
However, I didn't recall Silver getting the special MA Senate election of Scott Brown wrong, and he seems not to have: (http://www.fivethirtyeight.com/2010/01/538-model-posits-brow...). It would have been surprising if he did, since it was an easy one. Were you thinking of a different election?