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That would be an interesting scenario...I imagine that Sauron (if he couldn't "control" Smaug) would at least try to make an ally of him. Rather like Morgoth and Ungoliant joining up to take down the Two Trees, each had something the other could profit from.
Hmm...maybe instead of just sending the Nazgul, Sauron could have sent Smaug to the Shire and laid it to ruin and then searched for the Ring in the ashes. Gandalf feared for Rivendell from the Dragon, I doubt the Shire could hold up longer than that.
But does Ringlust take hold on dragons, aside from their love of gold in general?
Very interesting thoughts.
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But all the while I sit and think of times there were before
I listen for returning feet and voices at the door
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