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Damn good question. Perhaps one of the largest plot holes of all time, aside from the Little Mermaid plot hole that my aunt just posted to her Facebook page. -But seriously, I can recall thinking "hey, why didn't they just do this earlier," when reading tLoTR as a kid. But, there's definitely a "this has to be the right confluence of events" type of scenario happening. The Eye of Sauron has to be distracted by the battle at the gate etc.....

I don't think it's so simple as flying a bunch of eagles in to mordor with Frodo and Sam atop them.

How fucking hilarious is it that I'm spending my time considering this though....? What a great book.