It is not the problem of the active vs. contemplative life alone that makes Strider so difficult to grapple with as a guide or guardian figure. The fact is that he talks more like Gandalf the Wizard than like a mere Man, yet he does not present himself with Gandalf’s qualifications for trustworthiness. And what respectable guide in classical or medieval literature simply shows up without qualifications? When Virgil appears to Dante, Dante recognizes him and learns at once that he is sent from Beatrice herself in Paradise. When saints appear in medieval tales as helpers of the lost, they show up in shining gold and white, with crowns or crucifixes or other indications that they are generally on the Right Side.

Strider, however, looks more like a rascal from the beginning. In fact, if I had to give him a counterpart from medieval or Renaissance literature, the closest would probably be the figure of the Devil, and especially of Mephistopheles. Strider appears suddenly, as Mephistopheles appears to Faust; he promises guidance and understanding, for a certain price (the price of trust… which is rather like selling one’s soul); he has powers that seem supernatural at times; he knows dark secrets. Intriguingly, the puzzle of his character brings to Frodo’s lips two adjectives that themselves have overtones of devilry and witchcraft in English literature.

“I think,” (Frodo says of the Enemy), “one of his spies would—well, seem fairer and feel fouler, if you understand.”
“I see,” laughed Strider. “I look foul and feel fair. Is that it? All that is gold does not glitter, not all those who wander are lost.”

At another time and in another place, another man who was destined to become King was accosted with similar language:

Fair is foul, and foul is fair,
Hover through the fog and filthy air.

Fair being foul and foul being fair is an apt way of summarizing the problem of Strider. Tolkien makes much of the fact that Strider is not what he seems to be. All that is gold does not glitter. There is, in fact, a traditional English saying that “All that glitters is not gold”, which phrase also shows up in another one of Shakespeare’s plays (The Merchant of Venice), though not in a context that sheds much light on the situation of Strider. (The phrase seems to have been common enough without Shakespeare’s help.) But Tolkien inverts this phrase to fit it to Strider. Common lore is ripe with warnings about evil disguising itself as good, fool’s gold passing itself off for real gold, the Devil appearing as an angel of light. But what if good disguises itself as evil, and gold disguises itself as lead, and the angel of light dresses up as the Devil? Don’t we need a useful maxim for those situations? Is Strider, in fact, the Devil inverted?

Perhaps this is why Strider escapes classification as a guide-figure. Tolkien may have been the first storyteller, on a grand scale, to attempt the inversion.