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Notes -
For the purposes of assassination I don't care which one is the evilest. I'm not here to punish them individually for being evil, I want to do damage to the Evil Empire.
Killing a true believer and especially a sympathetic true believer seems like a great way to consolidate the Evil Empire followers around a martyr. Instead I'd say the plucky rebels should assassinate Bob, to send a message to the most apathetic, opportunist and amoral Evil Empire henchmen (which I expect to be the majority) that rather than the most loyal or the most efficient, it could be any one of them.
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