Question: Why was Little Bill so protective of the two cowboys that had bounties on their heads? And why was he so vengeful when they were both killed? He didn't know them.
Gavin Jackson
28th Jul 2015
Unforgiven (1992)
Answer: Little Bill wanted to be sure that the cowboys would live at least long enough to pay compensation to the owner of the saloon/brothel for disfiguring one of the prostitutes; Bill became furious when the cowboys were killed because they would never be able to make good on their agreement of compensation.
The cowboys bring in their ponies and pay off their debt early in the film. "Davey Boy" even brings in an extra pony especially for Delilah, which he calls the "best in the lot." (Which the other whores promptly reject and begin throwing dung at them). Both cowboys are killed long after they pay their debt to Skinny.
There is a scene where the two cowboys come to town and pay the required compensation in horses.
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Chosen answer: I think Little Bill takes offense to this sort of thing taking place in his town on his watch. He tells Mr. Beauchamp while he is writing his biography something like, "I do not like assassins, or men of low character."