In the very first section, the rabbis grapple with the verse, "You have circled this mountain enough" (Deuteronomy 2:3). What does it mean to circle a mountain "enough?" They see in this verse a deeper struggle, a timeless conflict.

The rabbis connect this verse to another, from Psalm 60:11: "Who will lead me to the fortified city (matzor)?" And here's where it gets interesting. The rabbis identify this "fortified city" as none other than Rome. But why would King David, centuries before Rome's rise to power, be yearning to conquer it?

Well, the rabbis aren't just talking about a physical city. They're talking about an empire, a symbol of oppression and exile. They play on the word matzor, "fortified," pointing out that it sounds like shemetzera, "that which torments." Rome, they say, is a city that "torments and fortifies Israel." How so? By causing them to repent, which thereby fortifies them! A fascinating idea, isn't it? That even in suffering, there's a path to strength.

The text goes on, offering other interpretations of "fortified city." It's a city fortified on all sides, impossible to conquer. It's a city that everyone fortifies, an empire drawing on the resources of many nations.

Rabbi Yoḥanan imagines David yearning, crying out, "If only I could exact punishment against it!" But can David, can anyone, truly overcome such a power? God responds, in this midrashic retelling, by asking David if he's truly up to the task.

David replies, "The One who already gave me dominion over Edom, He will give me dominion over this great one!" He argues that if God helped him conquer Edom, surely He can help him conquer Rome.

Where does this idea of David's dominion over Edom come from? The text points to II Samuel 8:14: "David placed netzivim in Edom." Now, netzivim is a tricky word. Rabbi Simon says it means "officials." But other Rabbis say it means "statues" – statues of David! Can you imagine? Statues of David, a constant reminder of his power, standing in the heart of Edom.

Rabbi Yehuda ben Rabbi Simon adds a beautiful layer. God says to David, "I know that your hands are quick and industrious, and I seek to subdue My world with them." It's a powerful image: God entrusting David with the task of shaping the world. But then, God adds, "David, I need them [Edom] for the generations."

Here's a twist. Moses himself sought to confront Edom, but God stopped him, saying, "You have circled this mountain enough (rav laḥem)." The text interprets this as God telling Moses to command the Israelites to circle the mountain. In other words, not every battle is meant to be fought head-on. Sometimes, circling, waiting, is the right path.

So, what does it all mean? This passage from Devarim Rabbah isn't just about Rome, or Edom, or even King David. It's about the challenges we face in our own lives. The seemingly insurmountable obstacles that loom before us like fortified cities. It's about recognizing that sometimes, the path to victory isn't a direct assault, but a patient circling, a willingness to learn and grow from the very things that oppress us. It’s about trusting that even when we feel like we’re going in circles, we are still on a path, guided by something larger than ourselves. And perhaps, most importantly, it's about understanding that even in our struggles, we are part of a larger story, a story that stretches back to Moses and David, and continues on through us.