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One additional unlikely event happening, or even one event being a foregone conclusion rather than a coin flip, will wipe out massive gains from model improvements, sometimes across thousands of predicted events.

Note: Assuming we are talking about binary predictions

It is true that one unlikely event happening can have arbitrarily high cost, but in practice people only bet up to the ~99% confidence level, so at most they incur log(0.01)=-4.6 nats of penalty. 

It is not true that a foregone conclusion that was predicted as a coin flip can cause massive gains. By definition it costs log(0.5)=-0.69 nats, regardless of the outcome.

Hover the course of thousands of events neither of these costs is massive. I agree that the scale is very difficult to reason about