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Not quite sure, but - King Eärnur of Gondor? Thrice challenged by the Witch King, twice denied his desire to 'stand and fight' (first by his horse, then by his Steward), third time he rode to Minas Morgul but was (presumably) taken captive and tormented to death -> end of royal line in Gondor. But I'm at a loss to explain 'twice bereaved' and what friends he made in the process.
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Und aus dem Erebos kamen viele seelen herauf der abgeschiedenen toten.- Homer, Odyssey, Canto XI
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