What if Gollum had lived?

[Moonraker]

Originally Posted by Andsigil

Pure speculation about the thoughts of a fictional character. In any event, being a dirtbag doesn't prevent one from being in a sad story.

Nope, not speculation. If Gandalf thought Gollum as evil regardless of what influence the Ring had on him, he would not have offered pity, he would have ordered jail at the very least, or death. Instead, he thought Gollum had a small chance of being cured from the evil of the Ring, and had him treated well by the Wood Elves. Tolkein even suggests that the archers of Gondor killing him in the dark would also be against Gandalf's wishes. The creature was not wholly evil or wicked in origin, and deserved a second chance, to his mind at least.