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How can we judge the accuracy of Nate Silver's predictions?

Firstly, he gives probability of outcomes. So, for example, his predictions for the U.S. election is currently 82% Clinton vs 18% Trump.

Now, even if Trump wins, how do I know that it wasn't just the 18% of the time that he should've won?

The other problem is that his probabilities change over time. So on July 31st, it was almost a 50-50 between Trump and Clinton.

My question is, given that he has a different probability every day for the same future event with the same outcome, how can I measure how accurate he was for each day he made a prediction based on the information that was available up to that day?