Why was it a pity that Bilbo didn't kill Gollum? How does Gandalf reply to this statement and what does Frodo learn from Gandalf's comments?
Though Frodo meant this in a negative sense, Gandalf spins his comment to a higher, more literal level. Pity was what stayed Bilbo's hand, a deeper sense of morality. Frodo believes that much evil could have been prevented by killing Gollum, yet Gandalf views Gollum's death as the loss of opportunity to do good (as the end of the novel proves).
When Frodo says that Gollum deserves death, Gandalf replies, "Deserves death? Many that live deserve death, and many who die deserve life. Can you give it to them? Then do not be too quick to deal out death in punishment, for even the very wise cannot see all ends."
Perhaps on a deeper level, Tolkien is making a statement about capital punishment, but in this particular case, he is speaking more about a transcendent Cause in the realm of Middle Earth. As a staunch Roman Catholic, Tolkien had a deep belief in Grace, in which God works in human life...
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