The Blessing Yitzchak Really Intended

Parashat Toledot is a Tale of Two Blessings. But this tale is puzzling on several levels and demands to be understood. Rabbi Paul Bloom looks at a way to navigate a path through this maze of issues.

In the second half of Parashat Toledot, Sefer Bereishit Chapter 27 revolves around a dramatic pair of questions: Who will receive Yitzchak’s great blessing?  Who will be chosen to carry the covenant forward into the next generation—Yaakov or Eisav?

We would assume that the blessing Yitzchak plans to give is the blessing of Am Yisrael: the charge to be “a blessing to the nations,” the spiritual legacy of Avraham Avinu, the bond with HaKadosh Baruch Hu, and the eternal connection to Eretz Yisrael. But when the blessing arrives, it is… surprising.  Almost disappointing. Instead of a grand spiritual vision, the blessing Yitzchak gives sounds like a financial and political one: dew of the heavens, fat of the land, power, wealth, dominance. Not the covenant of Avraham, not the spiritual destiny of Klal Yisrael—just prosperity and influence.

What happened?
 Where is Eretz Yisrael? Where is the mission to bring blessing to the world?  Why is the blessing so materialistic—so un-Avraham-like? These questions, however, lead us to the deeper understanding of the entire parasha.

Was Yitzchak Really “Fooled”?

Chazal and the classical mefarshim reject the simplistic reading that Yitzchak was gullible. Yitzchak Avinu—the spiritual giant, the patriarch—was not naïvely tricked by a bowl of food and a costume.

Following the approach of the Malbim and the Sforno, we see a completely different picture: Yitzchak knew exactly who his sons were.

●      He knew Yaakov was the “ish tam yoshev ohalim,” the spiritual heir, the one destined to carry the covenant.

●      He knew Eisav was a man of action, strength, charisma, and worldly capability.

And Yitzchak believed that each son had a role to play.  His dream—his vision—was a partnership, a partnership like the later model of Yissachar and Zevulun, where:

●      Yissachar dedicates himself to Torah

●      Zevulun engages the marketplace

●      The two support, respect, and need one another.

Yitzchak envisioned Yaakov as the spiritual leader but Eisav as the powerful national leader: the financier, the military protector, the political force. Yaakov would teach Torah, spread emunah, and carry the covenant. Eisav would provide the material infrastructure for that mission.

This was a brilliant plan—if it could work

Thus the blessing Yitzchak gives—thinking Eisav is before him—is not the blessing of Avraham. It is the blessing of worldly power, the blessing of a national partner who would support Yaakov’s spiritual mission. Yaakov would receive his blessing later—the true birchat Avraham—in Chapter 28, Yitzchak explicitly gives him:

●      the covenant of Avraham,

●      the relationship with Hashem,

●      and the promise of Eretz Yisrael.

That was always meant for Yaakov. But Yitzchak hoped for a partnership.

Why the Plan Failed

But one person saw what Yitzchak did not: Rivka. She knew Eisav more deeply, more honestly. She knew that Eisav was not simply a strong, worldly personality—he was fundamentally self-centered. His talents and drive were aimed inward, not upward. He lacked the anavah, the discipline, the spiritual sensitivity to use power for a higher purpose.

Yitzchak dreamed of Yissachar and Zevulun. Rivka saw Korach. Had Eisav received material power, he would not have shared it with Yaakov.  He would have used it for himself—not to build a nation, but to feed an ego. Therefore the partnership could not stand. That’s why Rivka ensures that Yaakov receives the first blessing as well—not because Yaakov needed the power for its own sake, but because Eisav could not be trusted with it.

Yaakov would now have to carry both responsibilities:

●      the spiritual leadership

●      and the material-national leadership.

And for that, he is sent to the “Harvard Business School” of Lavan, to learn the worldly skills necessary to guide a nation.

A New Understanding of “I Already Gave the Blessing”

This interpretation also explains one of the most puzzling moments in the parasha. Eisav begs:
 “Haven’t you a blessing for me, too, Father?” And Yitzchak essentially answers:  “I’m sorry—I already gave it away.” But why should this be so?  Are blessings like coupons that can be used only once? Can a gadol ever say, “Sorry, I’ve run out of berachot”?

The answer is profound: A true berachah is not “I wish you wealth, success, power, beauty.”
 That is just good fortune. That is not a Torah concept of blessing. A Torah berachah is:
 “May you have success and use it for a spiritual purpose— for building Torah, for elevating others, for bringing Hashem’s presence into the world.” If a person cannot or will not use success for spiritual ends, no true berachah is possible.  Yitzchak is not refusing—he is recognizing reality.

The Dream for Klal Yisrael

What emerges from this parasha is a blueprint for Jewish society: The Jewish people need both forms of leadership—spiritual and material.  Both are holy.  Both are necessary. But the key is mutual respect.

Imagine a society—imagine Eretz Yisrael today—where:

●      The military and economic leaders view Torah scholars not as a burden but as the moral and spiritual backbone of the nation.

●      And the benei Torah view the soldiers, workers, innovators, and officials not as distractions but as essential partners in building a Jewish state.

That was Yitzchak’s dream.  It remains the dream of Mashiach ben Yosef and Mashiach ben David— a perfected partnership of strength and spirit. Rivka understood that it was premature in her day.  But the dream remains.

Our Role Today

We live in a time when these tensions are real—perhaps more visible than ever.  And yet the parasha calls us to strive for Yitzchak’s vision:

●      To honor those who protect and build the physical nation

●      To honor those who preserve and teach the spiritual nation

●      And to foster deep respect between them, as partners, not adversaries.

This is not only possible—it is our destiny.

Yehi Ratzon

May we merit to see a generation in which the strengths of Yosef and Yehudah, of Yaakov and Eisav’s potential, of Yissachar and Zevulun, unite to build an Am Yisrael that is both strong and holy, prosperous and humble, powerful and profoundly connected to Hashem.

May that partnership lead us swiftly toward ge’ulah.

The Quiet Strength of Continuity: Toledot 5786

This piece was first published in yesterday's Hanassi Highlights.  To read it in Ivrit, courtesy of AI, click here.

n March 1921 Winston Churchill, the British Colonial Secretary of the time, visited the young city of Tel Aviv. Eager to present the best possible impression, Meir Dizengoff, the city’s mayor, arranged for palm trees to be planted along the still-bare Rothschild Boulevard. As the procession moved down the street, the crowd began to climb the newly planted trees to get a better view. The trees promptly collapsed. Churchill turned to Dizengoff and remarked dryly: “Roots, Mr. Dizengoff—without roots, it won’t work.”

That observation serves as an unexpected introduction to Parashat Toledot, the only parasha focused squarely on Yitzchak Avinu. If Avraham’s life is marked by drama, movement, and sweeping transformation, Yitzchak’s seems almost muted by comparison. He stays in the Land and avoids conflict. The Torah devotes its longest narrative about him to the redigging of wells his father had dug—even preserving their original names.

Yet it is precisely here that we encounter the depth of Yitzchak’s greatness.

Beginning a revolution is bold; ensuring that it endures is far more demanding. Avraham’s role was to introduce an entirely new spiritual vision to the world. Yitzchak’s was to ensure that vision took root—that it would not disappear once the initial excitement faded.

But genuine continuity is never mere imitation. Yitzchak could not simply repeat Avraham’s actions; his world was different, his generation different, and the spiritual challenges he faced required a distinct response. Redigging the wells was an act of renewal, not nostalgia: the same water, the same values,but drawn in a way that his generation could understand.

Rav Soloveitchik notes this idea in his explanation of the Midrash that Avraham and Yitzchak looked identical. Rashi explains that this was to silence the “leitzanei hador” —the scoffers of the generation—who questioned whether Avraham had truly fathered Yitzchak. Rav Soloveitchik explains that the critics of the time were not merely questioning biological lineage. They were doubting whether Avraham’s achievements could truly be transmitted. Could a new generation genuinely carry forward the ideals of the previous one? Would Avraham’s covenant endure, or would it fade with him?

The Torah’s emphatic answer, “Avraham holid et Yitzchak”, affirms that the legacy did, in fact, take root. The values endured. The wells flowed again.

This remains one of the central tasks of Jewish life. Each generation receives a precious inheritance, yet each must dig again. Circumstances shift, language shifts, cultural assumptions shift—but the underlying waters remain unchanged. The work of preserving the mesorah is not passive; it calls for sensitivity, wisdom, and creativity.

Yitzchak reminds us that continuity is courageous. It is the quiet heroism of ensuring that something ancient remains vibrant and life-giving even as the world changes around it. May we continue to draw from those wells with strength and clarity.

Shabbat Shalom, Rabbi Joel Kenigsberg

Family, foes and painful choices: Toledot 5785

The troubling question on this week’s parsha that has persisted throughout the ages of biblical commentary is: Whatever is Yitzchak thinking when he plans to give the blessings and heritage of Avraham to Eisav? Basically, explanations fall into two categories. One view is that Yitzchak, fooled by Eisav, is quite unaware of his true nature and wanton behavior. Rashi, quoting Midrash, interprets that Eisav “hunted“ his father with his pious speech and cunning conversation. Yitzchak is taken in and believes that Eisav, a man of the world and a physically powerful figure, is better suited to carry on Avraham’s vision than is Yaakov, the more studious and apparently less sophisticated of the pair. 

The other opinion, more popular among the later commentators to the Torah, is that Yitzchak is aware of the shortcomings of behavior and attitude of his elder son. His desire to give the blessings to Eisav is due to his wish to redeem and save him, to enable Eisav to turn his life around and become a worthy heir to the traditions of his father and grandfather. Yitzchak thinks that even if he gives the blessings to Eisav, Yaakov will not really suffer any disadvantage in his life’s work, while Eisav will find his way back to holiness through the blessings that he will have received. 

These two divergent attitudes towards the wayward child in Jewish families are enacted daily in Jewish family life. Later Yitzchaks either wilfully allow themselves to be deluded regarding the behavior and lifestyle of children or, aware of the problem, they attempt to solve it through a combination of generosity and a plethora of blessings. 

Rivkah, the mother of both Eisav and Yaakov, is not fooled by Eisav’s apparently soothing words; nor does she believe that granting him blessings will somehow accomplish any major shift in his chosen lifestyle. To a great measure she adopts a policy of triage, saving Yaakov and blessing him while thus abandoning Eisav to his own preferred wanton ways. 

The Torah does not record for us the “what if” scenario of Eisav receiving the blessings. Would he have been different in behavior and attitude, belief and mission? However, from the words of the later prophets of Israel, especially those of Ovadyah, it appears to be clear that God concurred with Rivkah’s policy, holding Eisav to be redeemable only in the very long run of history and human events. 

The moral of this episode is that one must be clear-eyed and realistic about the painful waywardness and misbehavior of Yaakov’s enemies, be they from within or without our immediate family and milieu. There are many painful choices that need to be made within one’s lifetime and especially in family relations, and few pat answers to varying and difficult situations. Perhaps that is why the Torah does not delve too deeply into the motives of Yitzchak and Rivkah, being content merely to reflect the different emotional relationships each had with their two very different sons. The Torah emphasizes the role that human emotions play in our lives and does not consign all matters to rational thought and decision-making.   

Shabbat shalom, Rabbi Berel Wein