Strider is the strangest guide I have ever encountered in literature. I wish I could compare him to Virgil in Dante’s Inferno. Like the character of Virgil, Strider does not navigate the Hobbits merely through a certain geography, but through the complexities of a reality that encompasses many different orders of beings — not demons, sinners and saints, in this case, but wraiths and Men and Elves. In this sense, a slender comparison between the two guides might hold good. But Virgil is an epic poet and Strider is not; Virgil is dead and Strider is not; Virgil is sent by the saints, and Strider is not. Strider simply has no classical or medieval analog that I can think of.

To be sure, Strider’s skills on the geographical level are nothing to be sneezed at. He is a great tracker and woodsman; he follows the signs of footprints and can tell if a stone has been handled recently. He remarks (tongue-in-cheek, I am convinced) to Frodo that he has “some skill as a hunter at need”. (In Chapter 2, Gandalf calls Aragorn “the greatest traveler and huntsman of this age of the world.”) So on the one hand, Strider has something of the accidents of a Robin Hood, using his woodcraft to protect the innocent Bree-landers. On the other hand, Strider is fighting no Sheriff of Nottingham but a Sheriff of Mordor who happens to be a Dark Lord, and everybody in Bree-land who should be on his side instead thinks that he’s a rascal.

The comparison with Robin Hood is superseded because what stands out most about Strider is not his woodcraft but what I will call his liberal arts education. Like Gandalf, he is one of the few people Frodo encounters in his journey who can explain the present danger in terms of past episodes in the doings of Elves and Men. As he will prove later in Rivendell, he knows more history than Boromir, he has decades of experience in international politics (he served both Theoden’s father and Denethor’s), and in Minas Tirith he displays more knowledge of herblore than the lore master himself. Strider knows the languages of Elves and Men, both ancient and modern, and can recite long passages of poetry and elaborate on them at leisure, as if he were a professor in an overstuffed chair. In short, Strider seems to have had the Harvard University education of his day.

Who exactly in ancient or medieval literature combines both the active and the contemplative life like this? Perhaps Plato’s “guardian class” in the Republic is a possibility. Granted, the philosopher-kings never reckoned on losing their thrones… but if a philosopher-king had been dethroned, and that by an evil power who was attempting to enslave the world, what would he have done? Perhaps Strider is Tolkien’s answer.