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Originally Posted by Kuruharan
Now that you mention it, that is odd.
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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.
Going back to Mith's original queries, it occurred to me that HoME might offer some clues. My HoME-fu isn't what it used to be, but flipping around in
The Return of the Shadow and
Sauron Defeated suggests a couple of possibilities.
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.
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But it is most remarkable to find here [in an outline from 1939] -- when there is no suggestion of the vast structure still to be built -- that the corruption of the Shire, and the crucial presence of Gollum on the Fiery Mountain, were very early elements in the whole.
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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.
In the first chapter of
Sauron Defeated, Christopher Tolkien sums up a few of his father's different outlines which contemplate the events at Mt. Doom. In each version, Gollum seizes the Ring from Frodo, but various scenarios were considered from there -- he and Frodo wrestle and Gollum falls into the fire; Sam arrives and either pushes Gollum into the fire or tackles him into it in a suicidal blaze of glory; or the seemingly quickly discarded idea that Gollum, in a flash of redemption, would himself dive into the fire with the Ring.
Perhaps -- envisioning a scenario where Gandalf goes all the way with Frodo -- G imagined that his love for Frodo might allow him to help the hobbit give up the Ring at the supreme moment, just as he had helped Bilbo give it up earlier.