During the decisive “Council of Elrond” chapter in The Fellowship of the Ring, Gandalf suggests a plan that is not only dangerous but absurd: to walk into Mordor and attempt to destroy the One Ring of Power. It seems foolish, which een Gandalf admits, but the folly of the endeavor is the one string tied to hope:

‘Despair or folly?’ said Gandalf. ‘It is not despair, for despair is only for those who see the end beyond all doubt. We do not. It is wisdom to recognize necessity, when all other courses have been weighed, though as folly it may appear to those who cling to false hope. Well, let folly be our cloak, a veil before the eyes of the enemy! For he is very wise and weighs all things to a nicety in the scales of his malice. But the only measure that he knows is desire, desire for power; and so he judges all hearts. Into his heart the thought will not enter that any will refuse it, that having the Ring we may seek to destroy it. If we seek this, we shall put him out of reckoning.’

‘At least for a while,’ said Elrond. ‘The road must be trod, but it will be very hard. And neither strength nor wisdom will carry us far upon it. This quest may be attempted by the weak with as much hope as the strong. Yet such is oft the course of deeds that move the wheels of the world: small hands do them because they must, while the eyes of the great are elsewhere.’”

Because of how ridiculous the plan seems, Gandalf suggests that Sauron would never expect it. Those at the council would have not just the element of surprise, they would have a plan totally inconceivable to their enemy. Because Sauron does not just thirst for power above all other things. To him, there is no other thing. Power is all he desires. It is the lens through which he sees all things with his single great eye. So, while this eye can see to the far corners of Middle-Earth, it cannot see that the free people of its lands have other desires and loves.

But, even if one of Sauron’s servants told their master that there were those who would not use the ring, Sauron still wouldn’t understand. He would explain away this strange idea. All of their desires, he would assume, must be connected to power. Everything, Gandalf says, is weighed out on the “scales of his malice.” Even if he heard the plan, Sauron couldn’t comprehend it. This faith in Sauron’s single mindedness proves well founded. We never see any indication that Sauron understands Frodo’s intent. Even when he finally senses Frodo in the fiery heart of Mount Doom, he can only think in terms of power and possession. He focuses all his power on turning others to that purpose as well. And, so, all his dark designs are undone. Undone not by horses and chariots, not by sword and spear and hammer, not by the strength of the great, nor the power of a rival. But undone by weakness. Undone by selflessness. Undone by folly.

So it often is with evil. So it was with the “dark lord” of our own world, Satan, the prince of the air. His downfall was brought about by a plan that, to him, could only appear as folly. Obsessed with power, Satan could never imagine God emptying himself of all majesty and “taking the form of a bond-servant, and being made in the likeness of men” (Philippians 2:7). And Satan couldn’t imagine God choosing a poor young woman to be his vessel. And he couldn’t imagine this girl responding “Fiat mihi.” And he couldn’t imagine Christ choosing to conquer death by death. To Satan, the cross is folly. Selflessness is folly. Servitude is folly.

Tolkien was never one for obvious allegory but he makes quite clear the connection between the downfall of Satan and the downfall of Sauron. The Battle Before the Black Gate, the unmaking of the ring, and the destruction of the foundation of Barad Dur; all of this occurred on the date Tolkien translates from the Middle-Earth calendars as March 25th. This, not coincidentally, is the date we celebrate the Annunciation: the date Satan’s plans were undone as Christ took on flesh, Mary gave her magnificent “yes,” and a tremor ran to the far ends of the universe as God’s cosmic plan of redemption began to unfold.

Yet, while March 25th marks the climactic destruction of Sauron in Tolkien’s epic, the date is only the beginning of our victory. Satan has not yet been cast into the lake of fire and there are still plenty of evil spirits who, as the Prayer to St. Michael puts it, “prowl about the world seeking the ruin of souls.” We still struggle mightily and the evil in our world often seems to have the upper hand. In light of this, much of what we do can still seem like folly. And it’s been this way for a long time.

Whenever I hear the word folly, I think of T.S. Eliot’s poem, “The Journey of the Magi.” In his telling, the Wise Men don’t stroll effortlessly across the desert, singing their own catchy carol, fully confident in their astrological and theological predictions. T.S. Eliot envisions the journey as much more bleak, with a Wise Man as a rather disgruntled narrator, who regrets giving up “The summer palaces on slopes, the terraces,/ And the silken girls bringing sherbet.” This narrator is honest about the cost and discomfort of the journey filled with hostile cities, dirty towns, angry servants, and cold, fire-less nights. He recalls their dark journey with these lines:

At the end we preferred to travel all night,

Sleeping in snatches,

With the voices singing in our ears, saying

That this was all folly.

Surely every saint has heard that little voice sing, “This is all folly!” And maybe this is Satan trying to dissuade us from our journey. Or maybe it’s just our own voice, aware of how foolish our plan seems. But, take heart! For just as Sauron could not fathom a set of scales besides that of his own malice, Satan seems just as unable to see through our cloak of folly.

Caravaggio’s conversion of St. Paul. St. Paul who would later write, “We preach Christ crucified, to the Jews a stumbling block, to the gentiles foolishness.”

To Satan, it seems terrible folly for a man to swear to celibacy, give up his freedom, and join the priesthood. How foolish for a beautiful woman to cover her head and enter a cloistered life! How foolish for a man and woman to actually hold fast to their wedding vows through marital strife! How foolish the men and women who put away the pursuit of wealth and power! How foolish the martyrs who would spill their blood like water!

And, so, Satan’s plans are undone again and again. By the girl who says “Yes.” By the fisherman who leaves his nets. By the men and women who go into the desert to pray. By the nobleman who gives away his riches and lives as a servant. These saints, again and again, put on the cloak of foolishness, march into the heart of an evil country, and defeat the enemy.

Because, as Saint Paul says, the foolishness of God is wiser than men, and the weakness of God is stronger than men. Well then, let folly be our cloak!