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Strong conventional war generals who understand what it takes to break an enemies lines often times find themselves completely out of their depth when faced with an insurgency. Out of nowhere there comes an enemy that wears no uniform, hides among civilians and appears and disappears at a moments notice. Generals with a rigid conventional war thinking have a tendency to use heavy firepower on a population to get at small numbers of men which have a tendency of pissing off many more people.

I will start off with a general of first half of the 20th century as an honorable mention.

In the positive column; General Arthur MacArthur the father of he who shall not be named. Metal of Honor recipient in the Civil War... he seemed to learn the basics of getting ones troops out with locals and using carrots and sticks to find enemies hiding among them in the Indian Wars which he brought along with him to the Philippines. Probably his smartest move was mass hiring local paramilitaries and playing bad cop to Taft's good cop to defeat the insurgency at the cost of over four thousand American lives.

In the negative column; William Westmorland. Vietnam was a difficult counterinsurgency fight because the enemy had unlimited resupply and sanctuary outside of the country the Army rarely was allowed to touch. The insurgents also operated in numbers large enough that some massed conventional units were needed. However, Westmorland never understood that the war against the insurgents would be won or lost along with the population of South Vietnam as long as the insurgents weren't stupid enough to go conventional and avail themselves of American firepower. The insurgents finally gave Westmorland the battle he wanted in Tet breaking the backbone of the insurgency, but by letting it drag and with an overabundance of happy talk the offensive convinced the US public and political class the war was lost.
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