It’s a question that’s been wrestled with for centuries, and Sifrei Devarim 41 offers a beautiful, layered answer, drawing on imagery from the Song of Songs.

Let’s dive in. The verse from Song of Songs (7:5) reads, "Your eyes are like the pools in Cheshbon by the gate of Bath-rabbim." What could this possibly mean?

The text explains that "Your eyes" refers to the elders, the appointed leaders of the congregation. But it’s not just about seeing; it’s about insight. As Isaiah (29:10) says, "The L-rd has poured upon you a spirit of deep sleep, and He has closed your 'eyes' from seeing." This isn't a physical blindness, but a spiritual one. The elders, the wise ones, are meant to truly see, to understand beyond the surface.

And what about the "pools"? Ah, this is where it gets really interesting. The Sifrei tells us that just as you can't plumb the depths of a pool, you can't fully fathom the words of the sages. There's a depth, a complexity, that requires contemplation and study. It's not about a quick dip; it's about immersing yourself.

Then there’s "Cheshbon." Cheshbon, in Hebrew, means "accountings." Here, it signifies the careful deliberations and wise counsel that the elders undertake. It’s the process of thinking things through, weighing different perspectives, and arriving at a thoughtful conclusion. The Sifrei specifies that these "accountings" happen in the houses of study, specifically “by the gate (of study) frequented by the many (scholars)" — bath-rabbim. It emphasizes the importance of communal learning, of many voices contributing to the understanding of Torah.

But the imagery doesn’t stop there! The verse continues, "Your nose is like the tower of Levanon which looks towards Damascus." What does a nose, a tower, and Damascus have to do with anything?

The text connects this to Eliyahu (Elijah) the prophet. If you dedicate yourself to studying Torah, you should hope for the arrival of Eliyahu. This connection is drawn from God's command to Eliyahu in I Kings 19:15, "Go, return on your way, to the desert of Damascus." So, the "tower of Lebanon which looks toward Damascus" becomes a symbol of anticipation, of looking forward to the future redemption that Eliyahu will herald.

And this idea of redemption is further emphasized by Malachi (3:22-24): "Remember the Torah of Moses, My servant… Behold, I am sending you Eliyahu the prophet before the coming of the day of the L-rd, and he will turn back (to the L-rd) the hearts of fathers with (their) sons, and the heart of sons with their fathers." This reconciliation, this turning back to tradition, is the ultimate purpose of the Torah – “which I command you this day."

So, what’s the takeaway? It's not enough to simply read the words of the Torah. We must delve into its depths, engage in thoughtful deliberation, and anticipate the future redemption. The wisdom of the elders, the depth of the text, and the hope for Eliyahu – they’re all interconnected, guiding us on our path. The study of Torah isn't just an intellectual exercise; it's a journey of the heart and soul, a continuous process of turning back to ourselves, to our tradition, and ultimately, to the L-rd.