But before we leave the Shire, let's pay attention to a small, but decisive force upon which the entire story hangs: the Pity of Bilbo. The Pity of Bilbo, his choice to not kill Gollum, is this tiny stone thrown into the great pond of history, rippling out to be, in the end, the decisive act that brings about the defeat of Sauron.
In "The Shadow of the Past," Gandalf and Frodo are discussing Bilbo's encounter with Gollum in The Hobbit. Frodo declares, "What a pity that Bilbo did not stab that vile creature, when he had the chance!"
Gandalf's response to Frodo's murderous outburst:
"Pity? It was Pity that stayed his hand. Pity, and Mercy: not to strike without need...My heart tells me that [Gollum] has some part to play yet, for good or ill, before the end; and that when that comes, the pity of Bilbo may rule the fate of many..."The title of the chapter is apt. Bilbo's pity will indeed cast a very long shadow in the book. One act of pity and mercy in The Hobbit runs like a golden thread through to the very end of the story.
Notice also, as Fleming Rutledge points out, how Tolkien capitalizes Pity and Mercy in his response to Frodo. That's a sign from Tolkien that Pity and Mercy aren't just one off "random acts of kindness." Pity and Mercy are the way we participate in the providential "something else at work" in the world. Small though they may be, through this divine participation acts of Pity and Mercy are forces, like ripples in a pond, that affect and shape the history and destiny of the world. The smallest acts of Pity and Mercy can be, in the end, the most consequential, the points upon which history turns.