Is the Hobbit's Contract enforceable?
The dwarves would have some defenses, but in my opinion Bilbo would have a good case that the contract should be declared unenforceable because it is for an illegal purpose.
Of course, there are a lot of other factors which may affect the outcome. Exactly where is this contract going to be heard? It was signed in the Shire, but it was to be performed at the Lonely Mountain, which is under dwarf jurisdiction (or so they say) but it also may fall under the jurisdiction of Dale, which is presumably the closest civilization with working courts or judges (The Shire had constables and provincial officials, but there would be a real question of whether they could exercise jurisdiction purely because the plaintiff resides there). A better tactic may be to submit to the jurisdiction of Rivendell, where wisdom and neutrality would be easier to find.
There you go. Bilbo went through all that for nothing. If he had hired me as his lawyer, he would have stayed home comfortably, and not had to go through any more adventures. Neither would Frodo, I suppose. Which would mean that the One Ring wouldn’t have been destroyed.
There go the lawyers again, ruining everybody’s good time.
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