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I think that in some queer twisted and pitiable way Gollum would have tried (not maybe with conscious design) to satisfy both. Certainly at some point not long before the end he would have stolen the Ring or taken it by violence (as he does in the actual Tale). But 'possession' satisfied, I think he would then have sacrificed himself for Frodo's sake and have voluntarily cast himself into the fiery abyss.
I think that an effect of his partial regeneration by love would have been a clearer vision when he claimed the Ring. He would have perceived the evil of Sauron, and suddenly realized that he could not use the Ring and had not the strength or stature to keep it in Sauron's despite: the only way to keep it and hurt Sauron was to destroy it and himself together – and in a flash he may have seen that this would also be the greatest service to Frodo.
--Letter no. 246
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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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