WELCOMING SHABBAT

Shabbat is more than a day of refraining from worldly activity.

When experienced to its spiritual fullest, its holiness enlightens all other days of the week.

We invite you to enhance your Shabbat with these words of Torah.

 

Yakov in the light, Esaav in the dark with a family tree between them

PARASHAT TOLEDOT – The Clash of Two Worlds (Zera Shimshon 1)

PARASHAT TOLEDOT – The Clash of Two Worlds (Zera Shimshon 1)

Sakhai, Rabbi Yitzchak
November 20, 2025

Why does the Torah say, “These are the offspring of Yitzchak, son of Avraham”? This week’s parasha, Toledot, presents a linguistic and thematic nuance that Rashi highlights— one that reveals a deep spiritual insight into the intertwined destinies of Yaakov and Esav. Drawing on the Zera Shimshon, Rabbi Yitzchak Sakhai explains how holiness and opposition coexist, why Esav’s role was essential despite his descent into wickedness, and how the dynamic between kedushah and kelipah is at the heart of Jewish survival in exile.

The parasha begins with the phrase “Ve’eleh toldot Yitzchak ben Avraham” — a verse that at first glance appears redundant, since the Torah soon introduces Yaakov and Esav by name. However, Rashi’s seemingly obvious comment, that this refers to Yaakov and Esav, points to a deeper issue. The Zera Shimshon explains that the connective “Ve’eleh” [“And these are”] implies a link to the previous section, which discussed Yishmael’s descendants. Why would the Torah connect Yitzchak’s holy offspring to Yishmael’s line? Rashi also notes the unusual repetition of ‘ben Avraham,’ which serves to highlight that even Esav, though he later turned to wickedness, carried within him sparks of holiness inherited from Avraham.

To understand this, we must grasp a foundational idea in Jewish thought and Kabbalah: the concept of the kelipah — literally, the “shell” or “peel” surrounding a fruit. Just as the peel protects and preserves the fruit, enabling it to grow and develop, so too the kelipot — the spiritual “shells” or forces of negativity — play a vital role in the development of holiness [kedushah]. Holiness cannot grow in a vacuum. Without resistance, challenge, or inner conflict, there would be no true growth. If doing good were always easy, if there were no temptation, then mitzvot would lose their power to elevate the soul. The very value of a mitzvah — and the reward it carries — comes precisely from the presence of a force that tries to stop us. Overcoming that force is what makes the act meaningful.

This is why someone who is commanded to perform a mitzvah receives more reward than someone who does it voluntarily — because the one who is commanded experiences inner pushback and must consciously overcome it. 

In this framework, Esav represents the kelipah — the necessary opposition that forces Yaakov and his descendants to grow stronger, more refined, and more deeply connected to Hashem. Even though Esav later turned to wickedness, his spiritual role was essential: his resistance became the condition through which holiness could flourish. In this sense, he carried within him the sparks of Avraham and fulfilled, at least for a time, a divine purpose.

Furthermore, the Torah alludes to the complex legacy of Esav’s descendants. From him would come righteous converts like Antoninus, the Roman emperor who studied Torah in secret with Rabbi Yehuda HaNasi, and Onkelos, the Roman nobleman who translated the Torah into Aramaic. Their greatness shows that Esav’s lineage was not devoid of spiritual potential.

Finally, the Zera Shimshon reveals the overarching framework: Hashem informed Avraham that his descendants would sin and asked him to choose between Gehinnom or exile. Avraham chose exile — and Esav became the vehicle through which that exile would manifest. Since the destruction of the Second Temple, we have lived in Esav’s exile — the exile of Edom. Thus, the opening pasuk encapsulates a cosmic tension: the spiritual legacy of Avraham includes both Yaakov and Esav, both light and resistance — both blessing and exile.

“NOTE: The above is a summary based on the original teaching.”