While I agree that Ancalagon was probably the mightiest of all the dragons, I think you underrate Glaurung. He was extremely cunning, and (probably) much craftier than Ancalagon. While I'm sure he wouldn't beat the Black in a purely physical duel, his overall power rivaled that of Ancalagon because of his hypnotic powers. Give him his due credit. He was, after all, able to drive the strongest Man ever to madness and suicide.
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...where the instrument of intelligence is added to brute power and evil will, mankind is powerless in its own defence.
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