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I'd kill the gatemaster guy and go home, since this sort of thing has been whored endlessly in fanfiction, which I hate.
Looking back, I'd go through the right portal since Middle-Earth isn't my world and I can be more successful here anyway.
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"And forth went Morgoth, and he was halted by the elves. Then went Sauron, who was stopped by a dog and then aged men. Finally, there came the Witch-King, who destroyed Arnor, but nobody seems to remember that."
-A History of Villains
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