“But this is terrible!” cried Frodo. “Far worse than the worst that I imagined from your hints and warnings. O Gandalf, best of friends, what am I to do? For now I am really afraid. What am I to do? What a pity that Bilbo did not stab that vile creature, when he had a chance!”
“Pity? It was Pity that stayed his hand. Pity, and Mercy: not to strike without need. And he has been well rewarded, Frodo. Be sure that he took so little hurt from the evil, and escaped in the end, because he began his ownership of the Ring so. With Pity.”
– ch 2, The Followship of the Ring
Never had I pondered Bilbo’s relatively healthy mental state before upon the beginning of The Fellowship. Considering he had been in possession of The Ring for decades, there was little evil effect upon his soul by the time he does give up the ring to Frodo. The Ring had wielded such power over Isildur in times gone by, Sméagol in more recent times, and others, who had not even come into contact with The Ring. So why hadn’t it proved to be such a powerful evil once again, manipulating and affecting the mind of a content little hobbit after it had finally slipped away from the grubby Gollum and back into the world for its chance to reach Sauron once again?
As the wise Gandalf tells us – it’s because of pity. Pity can be translated into empathy, empathy to mercy, mercy to love. The pity Bilbo had in his heart for the pathetic existence of the creature Gollum is a character defining trait. Gollum was a trickster, an evil spirited being with no more moral compass then a snake. He was prepared, and even fastening a plan during their exchange, to kill Bilbo right then and there. And yet, when Bilbo had the upper hand, he showed this vile creature mercy. The first life and character altering decision Bilbo made when in possession of the ring was one of pity, of mercy, of love for a fellow creature. It is exactly as Gandalf says: Bilbo begins his ownership of The Ring with pity, with mercy, with love. Because of this very first decision he makes with such power within his grasp, evil is held at bay, it doesn’t consume him the way it did Sméagol – who, we know, made the opposite decision, and killed his cousin Deagol for the ring, which ultimately leads to the killing of any humanity within him. Instead of becoming an unrecognizable creature, Bilbo remains the same, save for his prolonged age, and definite desire to keep the ring in his possession.
The last decision Bilbo made with the ring – to leave it to Frodo – is connected to his very first decision. How, after so many years, was he able to (reluctantly, sure) able to leave it, to walk away from it? His very first decision regarding the ring was made out of love. Undoubtedly the decisions we make in life affect our later decisions. Selfish decisions encourage more selfish decisions, selfless decisions encourage further selfless decisions, giving into temptation once makes it harder to avoid the next time, just as standing strong against temptation makes it easier to stay strong the next time. His very first decision made out of love, against such an evil (an evil so strong it fills a pleasant hobbit mind with murder within minutes of touching it), would have given such strength to Bilbo’s soul. Despite decades of possessing the ring, he was still able to draw from that strength, courage, love, to leave the ring when he knew it was time.
Like Bilbo, we can also propagate strength through the good decisions we make, or propagate evil through the bad decisions we make. With every strong & good decision made against our human weaknesses, we gain graces, making it easier to choose good the next time. Likewise, every time we fail to make the good decision, we are pulled further down, making it that much more difficult to make the good decision next time. A seed can easily be dug up, drowned out, eventually lost and forgotten among a sea of weeds. Or, with tender and consistent fostering, it can grow into an oak tree, producing more fruits itself.