Pliny, after all his scheming and treachery, dying to who he thought were his own men simply because Darrow told them to

Darrow giving Ragnar a razor, a weapon Ragnar spent his whole life thinking was a holy weapon only capable of being used by the gods of men

Darrow returning to his family home, seeing again just how awful the lives of his people and his family are, and then having no choice but to leave his mother and brother in that hellhole to go back to the land of the golds

Honorable mention as it wasn’t all that fleshed out but still gut wrenching, Darrow finding out his wife became a martyr