Shaking a stick at somebody, of course, is a threatening gesture, or at least one of defiance. So to say that you have shaken a stick at somebody is to suggest that person is an opponent, perhaps a worthy one. The sense in the second and third quotations above seem to fit this idea: “nothing worth shaking a stick at” means nothing of value; “equal to any man you could shake a stick at” means that the speaker is equal to any man of consequence.
Following publication of this piece in the World Wide Words newsletter, Suzan Hendren and Sherwin Cogan suggested that it might have come from the Native American practice of counting coup, in which merit was gained by touching a vanquished enemy in battle. In that case, “too many to shake a stick at” might indicate a surplus of fallen enemies, and “not worth shaking a stick at” would equate a person with “an enemy who is so cowardly or worthless that there is no merit to be gained from counting coup on him”, as Sherwin Cogan put it. An intriguing idea, but there’s no evidence that I know of.
Let me summarise: nobody knows for sure.
Definition from Steve Sabram: 1) a military phrase of guerrilla warfare where you do not have much in weapons and you fight with what you get from the land (i.e. sticks). If you have so many people to fight or animals to hunt, you cannot count let alone chase them all. 2) Another I heard of is it is an old shepherding term where you have so many animals to herd, you cannot shake you stick at every individual animal to herd them.
David Windmueller: I remember reading in a book that it came from the revolutionary war. There was some scene where Washington was waving a wooden ceremonial sword over the British forces that he had just been victorious over.
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