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Who is the best insurgent leader in history?
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You have a criterion or set of criteria in mind for "best"? Best looking? Most effective? Militarily the best or politically or both? Best at a theoretical or practical level?
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You can list a small group if you can't pick one
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Just to start the ball rolling I will throw out two figures, at least one of whom doesn't normally come to mind when you think of insurgents and both of whom are known more for conventional military acumen than guerrilla warfare skills (but an insurgency has stages and involves a whole spectrum of military means): Gen. George Washington and Gen. Vo Nguyen Giap.
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Why did you pick who you picked?
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First names that came to mind. And to start the ball rolling.