However, I too felt such a tug at my heartstrings when Smeags brought them the conies. "Nice and fresh!" And when he thought he had banished Gollum. "We are free!" And when he was trying to catch the fish and Sam asked Frodo why he wanted to save him - the goofy grin on Smeags face when he looked at them from atop his rock perch in the river.
The most heartbreaking moment was when Gollum was comforting Smeagol after Frodo's betrayal. You just know that Smeagol was so desperate for comfort and friendship - Frodo had offered him that, but had to betray him to save his (Smeagol's) life. And that by saving his life, Frodo had restored Gollum to leadership. What sad irony!
So, Smeagol is a wretch of his own making at first then overcome by the ring. I have nothing but pity for him. He's ruined... and the only thing we have left is the glimmer of Smeagol who wants to be free but cannot.