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"Who is the best insurgent leader in history?"
First: Benjamin Franklin, US representative in Europe, American Revolution.
Second: Boris Yeltsin, Ex-President, Russian Republic
"Why did you pick who you picked?"
Both individuals met the following criteria:
1. Both individual were originally part of existing establishment, worked both inside (and eventually from outside/fringe) to functionally replace the existing system of governance with a radically different alternative form of governance.
2. Both individuals took extreme risks as part of their efforts on behalf of their respective insurgencies. If Franklin had ever been captured by the British, well, he would have been a dead man and that might well have been the end of the American Revolution.
3. Both were "successful" (on Yeltsin, jury is still out) in their "insurgencies", compared to many of the others mentioned here.
4. Both efforts were primarily "insurgencies", and not primarily "terrorist" in nature, as the goal in both cases was to establish a different type of government structure.
Just my .02
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