Ancalagon the Black was the first of the winged dragons. He was either the first or second greatest dragon ever (the other being Gothmog, who wasn't winged). He fought in the War of the Wrath on the side of Melkor, but he was slain in the sky by Earendil. He is mentioned, thus, in the SIlmarillion.
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"He was sent by a mere prudent plan of the angelic Valar or governors; but Authority had taken up this plan and enlarged it, at the moment of its failure."
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