Wan Shi Tong wrote:
You are all most definitely wrong, no offence. Gandalf got Aragon to help him hunt for Gollum before he was distracted by other tasks and left Aragon to the hunt. I don't believe the twins or any of Aragon's kin help much if at all. Anyhow Aragon caught Gollum so point after he left Mordor and took him to the closest safe house, Mirkwood to be held until Gandalf arrived. Gollum escaped from the elves after Gandalf interrogated him about the ring and Sauron. He did so by climbing up a tree when the elves let him out of his cell for a bit and wanting for a orc raiding party to kill his guards so he could leave.
Ah yes I remember now, Legolas explains this during the Council of Elrond. There is an implication that Legolas did encounter Gollum personally however, because he says 'we' would let him climb the trees and roam the woods. I admit that 'we' could be referring to his people, the Wood Elves as a whole, but because Legolas' account is quite detailed it seems more likely that he was part of the guard there with Gollum at the time:
'In the days of fair weather
we led Gollum through the woods; and there was a high tree standing alone far from the others which he liked to climb. Often
we let him mount up to the highest branches, until he felt the free wind; but we set a guard at the tree's foot. One day he refused to come down, and the guards had no mind to climb after him: he had learned the trick of clinging to boughs with his feet as well as with his hands; so they sat by the tree far into the night.'