NancyLebovitz comments on How would you take over Rome? - Less Wrong Discussion
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After backing the winning side once or twice, things change, and your knowledge of specific details of history will become less and less valuable.
I plan on displacing some other backer so that the total support is roughly the same, such that the events proceed as similarly as possible. Once the disjunct becomes too big, I have to actually think to pick the winning side, but that's not that much harder.