This is really cool! It's interesting that you can "cheat" by knowing the historical situation in advance. But I guess there's no way around that - if the situations involved were hypothetical, it would be unsatisfying when you guessed "wrong". It'd be neat to see really obscure examples drawn from history.
Yeah, I agree this post would have been better with a concrete example. It's hard to talk about a specific project though, since it comes down to describing in detail facts about a company's internal workings (often embarrassing facts). I couldn't figure out how to anonymize it sufficiently.