A quote that I always remember is when Gandelf is explaining to Frodo about Gollum in the shadow of the past and Frodo says that Bilbo should have killed Gollum when he had the chance "he deserves death"
Gandelf replies
"Deserves it, I dare say he does. Many that live deserve death. And some that die deserve life. Can you give it to them? Then do not be too eager to deal outh death in judgment. For not even the very wise can see all ends. I have not much hope that Gollum can be cured before he dies, but there is a chance of it. And he is bound up with the fate of the ring, my heart tells me that he has some part to play yet, for good or ill before the end. And when it comes the pity of Bilbo may rule the fate of many"
- Classic Gandelf
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