Perhaps the broader question is, why the effort to graft the Cottage of Lost Play onto the later Legendarium at all? It appears Tolkien rejected the concept very early on together with the whole Eriol story. (Whether he finally rejected or retained Aelfwine is another can o' worms).
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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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