Spoilers for The Hobbit, including the fate of the Arkenstone.

When Bilbo Baggins finds Gollum blocking his escape from the tunnels beneath the Misty Mountains, he has a sword and a ring that makes him invisible. He considers killing Gollum, then imagines what it must be like to live alone in the dark. Pity changes his mind. Bilbo jumps over Gollum and takes his chances with the tunnel ahead.

That decision is a turning point in J. R. R. Tolkien’s The Hobbit. Later, when Thorin Oakenshield refuses to bargain over the Lonely Mountain’s treasure, Bilbo uses the Arkenstone to give the people outside the mountain a way to negotiate. The scenes are chapters apart, but both ask what Bilbo will do when he has an advantage that other people are powerless to take from him.

How Bilbo learns to act while he’s afraid

At Bag End, Bilbo has good reason to wonder why Gandalf picked him as the company’s burglar. He has never done anything like this, and for much of the journey, the dwarves have their doubts about him too. His confidence grows as he discovers what he can do in a tight spot. In Mirkwood, he draws giant spiders away from the captured dwarves. Later, he works out how to smuggle the company out of the Elvenking’s halls in barrels.

Both escapes depend on Bilbo paying attention. He notices what other characters overlook and acts before he can be sure his plan will work. That same habit of looking closely matters in the tunnel, where he sees enough of Gollum’s misery to reconsider what he’s about to do.

Why Bilbo spares Gollum

The riddle game gives Bilbo a chance to talk his way out of danger. The harder decision comes after the game, when Gollum is between him and the exit. Tolkien gives Bilbo a moment to imagine Gollum’s life from the inside. His fear is still there, and Gollum is still dangerous. The leap lets Bilbo get away without killing someone who cannot see him coming.

It’s worth slowing down on a reread of “Riddles in the Dark.” Once you know Bilbo makes it out, there’s room to notice how briefly he holds the advantage and how quickly he has to decide what to do with it.

Why Bilbo gives Bard the Arkenstone

After Smaug’s death, Thorin shuts himself inside the Lonely Mountain with the treasure. Bard asks for a share to help the people of Lake-town, whose homes Smaug destroyed. Bilbo has secretly kept the Arkenstone, the jewel Thorin prizes above the rest of the hoard. He slips out of the mountain and gives it to Bard in the Elvenking’s camp, hoping they can use it to bargain with Thorin and prevent a fight.

The choice is harder to defend than the leap over Gollum. Bilbo makes a secret decision about an heirloom that means a great deal to Thorin, and Thorin has every reason to take it personally. But Bilbo has also seen what the standoff is costing people outside the mountain. He decides he owes them something too. The Arkenstone gives him a chance to act on that judgment at the risk of losing a friendship.

What to watch for on a reread

Pair “Riddles in the Dark” with “A Thief in the Night” and notice who gets a say in each scene. In the tunnel, invisibility lets Bilbo make a decision Gollum will never know he faced. Outside the mountain, Bilbo hands over the one thing that might persuade Thorin to listen. That’s a good thread to follow if you read fantasy for strained friendships and hard choices, or if you remember The Hobbit mostly for Smaug and the riddles.

As an Amazon Associate I earn from qualifying purchases.

Pick up a paperback copy of The Hobbit to revisit “Riddles in the Dark” and “A Thief in the Night” together.

For more on what makes the book worth revisiting, read our review of The Hobbit.

Follow us on Instagram and Facebook


Discover more from Books of Brilliance

Subscribe to get the latest posts sent to your email.