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Originally Posted by Mister Underhill
Actually, if Denethor had made the connection between "Isildur's Bane" and "Sauron's Ring", as Inzila and Faramir surmise upthread, it would go a long way to explaining why he'd allow Boromir to take on the errand. But even a more conservative reading of the situation allows for Denethor (who perhaps already had become quite hopeless about the prospects of Minas Tirith) approving a Hail Mary plan which at the very least would carry his favorite son out of harm's way, albeit temporarily.
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I just now noticed that the emphasis was not added because I stupidly italicized rather than bolding....oops.
Anyway, I was really noting the unescorted part of the trip. I find that quite odd. Even on a secret errand, surely somebody should have gone with Boromir just to make sure some minor mishap on the road didn't kill or injure him.
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The first, and perhaps least satisfying, explanation for the plan-that-must-fail is that Tolkien seems to have foreseen very early on that Gollum would be the true mechanism of the destruction of the Ring.
It would be easy to infer that this realization saddled Tolkien with a set of narrative blinders. He knew how the Ring would be destroyed, so it wasn't necessary for his heroes to conceive of an actually workable plan for its destruction.
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This is an excellent point.
However, in a way I think (if I may be so bold) that Tolkien would have agreed with my point regarding Gandalf that I made upthread. Ultimately, the issue had to be put in the hands of Eru.