You would probably find "The Disaster of the Gladden Fields" in The Unfinished Tales to be very interesting. Much of Isilsur's personality is revealed in that story.
I won't spoil the particulars of the story for you, but suffice to say that Isildur had a change of opinion regarding his pride and the Ring before the end of his life...
I suppose it might parallel Boromir in a way, at least so far as realizing a mistake.
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...finding a path that cannot be found, walking a road that cannot be seen, climbing a ladder that was never placed, or reading a paragraph that has no...
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