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^You would think so yes. I can think of three possible explanaitions why he didn't.
*Gollum might have been very young when he originally stole the ring. Had he been say 15 to 20 years old at that time his aging process might have stopped there. When he lost his ring he once again started to age but since hobbits often live beyond the age of a 100 years he would still be fairly vital at the time of the war of the ring. Didn't something like 60 years pass from the time he lost he lost the ring until the war?
*The suspended aging process caused by the ring might have affected Gollum more profoundly than it did Bilbo since he had it for much longer and (presumably) used it more frequently. The effect might have lingered on even after he lost it.
*Tolkien might have overlooked this.
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