Let's assume (I don't know if it is actually true or not) that in the history of the supreme court, there have never been two judges of the exact same seniority. In that case, a model learned from handshake data would not include the slightest hint of this unwritten social law.
I think what Chomsky is saying is that if we do not understand the generative principle behind any data, we cannot possibly know what circumstance might completely invalidate our model. There may not be a way to smooth this out.
Language understanding, contrary to things like speech recognition, does not lend itself very well to smoothing.