My vote is for Deagol and Smeagol.
Here we have 2 best friends, one of whom finds Shiny Object at far bottom of river, whereupon the other is instantly overcome with evil, magical jealousy and kills him! Thus, living out the rest of his (looooooong)days with no friends AT ALL, Smeagol goes on to become a completely miserable wretch! How much more unlucky can you be than to be the poor saps who find the One Ring and have no guidance whatsoever (like an ISTARI, maybe)?
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- Eve
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