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Riddles, not Swords Decide Gollum's Fate

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Nov 22, 2025
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More from The Hobbit that I can't help but notice and think on. Bilbo meets Gollum alone, lost, frightened, and armed with a sword he barely understands. By normal adventure rules, this is where violence decides the outcome. I mean, come on, That nasty little smelly creature was not going to let Bilbo go, and he knew it.

But Tolkien does something strange. Instead of a fight, we get a riddle game. That’s not accidental so much as it’s moral architecture.

Riddles require something of both participants:

listening instead of striking; patience instead of panic; recognition of another mind, even a broken one. When Bilbo Baggins plays riddles with Gollum, he is forced to treat him even if briefly, as a thinking being, not a monster to be slain.

And that matters.

Because when Bilbo finally could kill Gollum, he doesn’t. Not because Gollum deserves mercy, but because Bilbo has already learned how to see him.

The riddles prepare the mercy. I see here that Tolkien is quietly teaching us something utterly valuable.

Violence ends a threat.
Understanding interrupts a tragedy.

If swords had decided the encounter, Middle-earth would have lost something essential: Bilbo’s moral awakening; Frodo’s later chance; the long, strange road toward redemption, just to name a few off the top of my head.

So riddles, not swords, decide Gollum’s fate
because Tolkien believes that how you win matters more than winning.

And that is very un-modern, though very Hobbit-like, and very true.
 

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