You call that pity? I think Bilbo lacks any amount of courage. Remember my friend he is the one who wrote the historical narrative we have. No it's not pity it's simply a lack of courage to do the job right. Now look what the little sneak did during the battle of five armies. He slipped the ring on and passed out due to fear. I know that he contrived some far-fetched story but the truth is simple enough for those with the ability to look below the surface.
Samwise the cruelheart? No, calling him this merely shows your ignorance towards the most beloved hobbit. Now if you knew Samwise well enough, you would know that he was a master of psychology. With his knowledge Sam knew that the only way to heal Gollum of his malady was through keeping him still and tough love. You see Sam was merely trying to cure him and it almost worked but that poor wretch was simply too far gone even for master healer Samwise
Edit: For Fordim's sake. I like you TGWBS. Bilbo's okay too, but he still can't hold a candle to Samwise.