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Gandalf knows that Gollum is not entirely evil. There is still the good "Smeagol" side to him. Even though he is very wise Gandalf cannot see the ultimate fate of the Ring, but he senses that Gollum will have some part to play for good or evil, so, like he says, "the pity of Bilbo [and himself] may rule the fate of many."

Also, Gandalf is not the type of person who will kill recklessly. And he himself, good and powerful though he is, has been tempted by the Ring's power, so he can vaguely understand Gollum's misery. Gandalf is very much like Jesus, who was tempted by Satan and can understand, though not agree with, a human's lust for power and easily corruptible heart.
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15y ago

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The Ring of Power (the One Ring) had been in Gollum's possession for about five hundred years, and then it was stolen from him by Bilbo Baggins of the Shire.

In the best of cases, people are resentful of thieves, but the Ring was Gollum's 'precious'. The Ring had turned him away from sunlight and the wilderness, even kill his best friend for it, and as a part of its power made him love it. He was bound to the Ring, which is nigh impossible to give up willingly.

Bilbo Baggins stole this Ring from him -- though Bilbo realized the Ring had been in Gollum's possession, he chose to keep it and escape. While this thievery is understandable, Gollum's hatred for him is also quite natural.

The ring was not stolen, it was found. Bilbo later guessed that it was what Gollum had lost, but he did not take it away from Gollum, But he didn't give it back, either.

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15y ago
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Gandalf does not hate Pippin. It does not say he hates him anywhere in the book or the movies. Gandalf gets frustrated with Pippin in the beginning of the story as Pippin causes trouble and does not understand the seriousness of whats going on. by the end of the book Pippin has matured greatly and Gandalf respects him greatly

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14y ago
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if Bilbo loses the riddles contest Gollum intended to eat him and take back "his precious" or the ring.

Bilbo feels pitiful about Gollum whereas the goblins and trolls want him dead

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12y ago
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Bilbo recognized that Gollum used to be much like him, and that he had the potential to become just like Gollum. He knew the pull the ring had on Gollum.

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9y ago
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Q: Why does Gandalf hate Pippin?
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