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Let's try to keep in mind, though, before we start getting all Talmudic about every word of text, is that everything we and even Tolkien have to say about this section is essentially ret-conning.
The Bombadil chapters were written very early, before Tolkien even knew what the Black Riders were (he thought at the time they might be horsed Barrow-Wights), and envisioned Bombadil halting pursuing Riders with a word and a gesture; this all goes back to the earliest "phase" of writing and barely underwent any revision, save the addition of Sam Gamgee, and switching "Bingo's" (->Frodo's) dreams around the better to fit the timeline elsewhere. "Trotter" (->Aragorn) didn't even exist yet, and Gandalf's whereabouts were a complete mystery.
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The entire plot of The Lord of the Rings could be said to turn on what Sauron didn’t know, and when he didn’t know it.
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