This shiur is Koheles with Rashi, but it's not quite the World of Medrash. I thought it was worth including anyway.

A look at a unique moment in history

This shiur is based on the Gemara Sanhedrin 107a, which deals with a medrash of how Dovid asked to be tested and then sinned.

About how to relate to a King (as not a replacement of God)

Why does Rashi say that Hashem told Yehoshua not to kill all of Amalek in the first war? What was the purpose of leaving evil around?

Two different shiurs somewhat connected

This episode draws parallels between midrashei aggadah and halacha to explain and justify the idea of the World of Medrash and Rashi's role in it.

Many of us grew up hearing midrashim as colorful additions to the stories of the Torah. As adults, we often wonder what to do with them. Are they meant to be literal? Are they always metaphorical? Why do some midrashim feel fantastical while others seem to shape halacha itself? And how can Moshe’s height or Og’s strength appear in a serious halachic discussion without anyone questioning the historical details?

In this episode I explore the system beneath the midrashic world. I look at examples from Shabbos and Berachos, where midrashim that seem impossible at first glance actually reveal consistent rules. I show how the Rashba describes midrash as a language with its own internal reality, where ideas can be expressed in ways that do not match history but still convey truth. And I examine how Rashi chooses specific midrashim to build a unified narrative that illuminates the pesukim without contradicting them.

What emerges is an entirely different way to read midrash. Instead of asking whether it happened, the real question is what idea the midrash is constructing and how it fits into the larger system of Torah. Once that framework is clear, midrashim stop feeling random and begin to form a coherent world of meaning.

World of Medrash explores the deeper architecture of Rashi and Chazal and uncovers the hidden structure beneath the stories of the Chumash.

There is a puzzling line in the Torah that most people skim right over. Before the flood, the psukim say that “all flesh had corrupted its ways.” Rashi explains this includes the animals. They were mating across species. That raises a difficult question. How can animals, who do not have bechirah, become corrupt in a moral sense? And what does it mean that they were punished along with mankind?

In this episode I explore how Rashi and the Midrash frame the corruption of the generation. The psukim describe a world filled with cruelty, lawlessness, and immorality. According to Chazal the animals mirrored that corruption, but not because of any moral choice on their part. The midrash hints to a deeper relationship between human behavior and the natural world. What happens to the world when society reaches a point where even animals imitate the breakdown around them?

I also look at the command that both humans and animals refrain from mating on the tevah. Why would animals be included in that restriction? What lesson is the midrash trying to reveal by saying that they earned merit for their behavior in the ark?

By reading the midrash literally rather than dismissing it as impossible, a new idea becomes visible. Human morality shapes the world around us in ways we rarely consider.

World of Medrash uncovers the hidden structure beneath familiar stories and reveals how Rashi and the Midrash bring the Chumash to life in unexpected ways.