Don't know about 5 but Smaug laid waste to cities all by himself. Granted NYC is much bigger but a single Leviathan didn't seem to be nearly that big of a threat. I feel like he could get to 5 at least.
@amendment50: Smaug solo'd medieval towns. He'd get rekt by modern firearms and a Fighter Jet which he would never see kill him.
He stops at The Leviathan. Possibly George would be enough if he can avoid or tank the fire and bring Smaug down to Earth. Smaug was not even strong enough to solo the armies of medieval men without flight. George wouldn't have this issue.
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