Much like many of the creatures which inhabit Middle Earth, dragons are somewhat of an enigma. Their origins are unclear, as is their size and shape. Yet one thing is fairly clear about Tolkien’s dragons: their cunning.
As previously discussed, in “Dragon Glamour and the Corruption of the Natural Law” with regards to Glaurung, the power of the dragons of Middle Earth is derived primarily from their glamour. Yes, in both the case of Glaurung and Smaug there is their great strength and poisoned or fiery breath, but what makes them more than a beast, more than a mere tool, and truly evil is their “great cunning and wisdom” (TBoLT II 86).
While Frodo’s statement that “the Shadow…can only mock, it cannot make: not real new things of its own” is primarily a reference to the nature of orcs and other creations of the Enemy, by extension it may be applied to the verbal utterances of the dragons (LotR 893). There is a striking link between the conversations of Smaug and Glaurung: both distort Truth. The power of the dragon is based on their ability to present falsehoods as Truth. What makes resisting that power near impossible is the fact that in creating deception and inducing calamity they use truth for their ends.
This is what makes Glaurung’s declarations to Túrin and Niënor so potent; he always speaks truthfully, though often in half-truths through crafty omissions and a knack for the proper delivery. Smaug, as a descendant and presumably weaker scion, retains this skill.
Believing, after the first trek to Smaug’s lair that he has no more to fear, Bilbo journeys into the darkness once more. This time Smaug awaits him.
Like so often before, the subsequent scenario mirrors Bilbo’s previous adventures in style and substance. Like the Trolls, Bilbo is attempting to sneak upon an enemy with the primary purpose of gathering information and is caught. Like “Riddles in the Dark,” he is confronted by a wily creature hungry for his destruction, who he must both outwit and outrun. And like the spiders, he will fight relying on his wit rather than the sword. It is through this repetition that the truly remarkable arc of Bilbo’s character is displayed.
Bilbo fights Smaug in the only way he can, through riddles and flattery. The reader is told this “is the way to talk to dragons;” and Bilbo does admirably until he becomes a bit too proud of his riddling and reveals too much (TH 259). Smaug soon moves on to describe the nature of Dwarves, planting the seeds of doubt in the Hobbit’s mind: what reward would the dwarves give him? How would it return to the Shire?
Each point is calculated and true. They are facts which the Hobbit never considered (though he previously mentioned the impossibility of carting the treasure out himself) and it is later seen that the dwarves never considered this eventuality either. Smaug speaks Truths, but they are Truths couched in sinister deception, and Bilbo is nearly caught. “Smaug [has] a rather overwhelming personality” and the deception hits so close to the mark that Bilbo almost succumbs, coming to verge of revealing himself (TH 260-1). For these are doubts Bilbo certainly has dealt with before, what with the constant ingratitude and selfish dependence of the dwarves. He has seen over and over again how inconvenience, greed and discomfort turn them. Their gratitude is a situational thing, only given grudgingly or when events go well. Given this, who is Bilbo to believe?
With an effort, Bilbo rejects the half-truths, and holds fast to friendship and loyalty, and reveals their mission: Revenge (TH 261). Being full of pride and confident in his own strengths, Smaug scoffs at the idea, and soon succumbs to Bilbo’s flattery, revealing his fatal flaw.
This episode repeats a common thread in Tolkien’s mythology: how the power of Evil is defined by an absence of Good and how the decent into Evil and its ultimate destruction is often through the sin of Pride.
There is an interesting link between this conversation with Evil and one presented in CS Lewis’ Space Trilogy. On the planet Perelandra, in a series of events mirroring the fall of Eden, Weston tempts the Lady through twisted Truth. In a horrifying and seemingly unstoppable series of events, the Lady is corrupted step by step. Though published in 1944, long after the debut of The Hobbit, the same disturbing facility of Evil to use Truth for its own ends is present in both works.
The conception again returns to the nature of evil. This is a question both authors address in their writings. In most cases, Tolkien’s portrayal follows the theories of Boethius, though it is never clear-cut. Often elements of Manichaeism are mixed in.
However, with regards to Evil’s skilled manipulation of Truth, the common element lies in the faith of both men. The Devil is given many names, one of which is “Father of Lies.” In Scripture, he is a great Tempter, often spinning lies to instill doubt. He is described as a serpent, even a dragon. He is known as the devourer, the deceiver and the slanderer.
This does not mean Smaug, or Tolkien’s dragons are devils, rather as Satan is the epitome of Evil in Christian thought his attributes are woven into the nature of the Shadow in both Tolkien’s and Lewis’ secondary worlds. In The Hobbit, Evil is further diluted to conform to the tale’s childlike nature. There is wit and even wry humor in Bilbo and Smaug’s exchange. Yet buried beneath is the same sinister darkness.