Smaug (Hobbit films)
In The Hobbit: The Desolation of Smaug, Smaug refers to Thorin by his title of "Oakenshield". Thorin did not gain this title until 29 years after Smaug took Erebor. The only ways Smaug could have known this are:
He could have communicated with Sauron, who presumably knew Thorin's title.
He could have used some kind of magical intuition to discover this.
Glaurung (The Silmarillion)
Glaurung knew about Túrin's past, which the latter had kept fairly secret:
"Thankless fosterling, outlaw, slayer of thy friend, thief of love, usurper of Nargothrond, captain foolhardy, and deserter of thy kin."
He knew about Túrin's family:
"If thou wilt be slain, I will slay thee gladly. But small help will that be to Morwen and Nienor."
He knew of Túrin's love Finduilas:
"And if thou tarry for Finduilas, then never shalt thou see Morwen again, and never at all shalt thou see Nienor thy sister; and they will curse thee."
He was not only aware that Nienor was pregnant, but also who got her pregnant (though he had planned it all out himself, I doubt he would have known for sure without magic):
"And now thou shalt know him: a stabber in the dark, treacherous to foes, faithless to friends, and a curse unto his kin, Túrin son of Húrin! But the worst of all his deeds thou shalt feel in thyself."
Orcs didn't tell him all this. Túrin wasn't exactly sending out info on his blog either. Glaurung obviously has some kind of superhuman intuition.
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