What if Gollum had lived?

[Inziladun]

Originally Posted by Moonraker

Gandalf thought the evolution of Gollum was a sad story, one that he thought could have happened to good law abiding hobbits, so he probably would not agree entirely with your assessment that Gollum was like you say before he saw the Ring for the first time.

Pity does not preclude holding one responsible for wrongdoing. Gandalf makes it clear to Frodo that because Bilbo's first act as Ring-bearer was to show mercy to Gollum, he escaped the Ring's corruption, and was even able to willfully give it up.

Gollum, on the other hand, began his possession of the Ring with murder, and then used it to spy on his relatives and learn their secrets.

Gandalf also felt sadness for the fall of Saruman, but we don't see him offering the latter a seat on the boat.