The Tragedy of Good Intentions
Family Edition

Toldot5785
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Toldot

Inspired by the teachings of Rabbi Lord Jonathan Sacks

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The Summary

This is an abridged version of the essay The Tragedy of Good Intentions written by Rabbi Sacks in 2011.

Near the end of Toldot comes the question, Why did Rivka tell Yaakov to trick Yitzchak and take Eisav’s blessing? As soon as Yitzchak announced he would bless Eisav, her plan created in great, without hesitation. She was determined to seize the moment. When Yaakov raised concerns (What if Yitzchak is not deceived? What if he touches my skin and knows immediately that I am not Eisav?) her reply is brief and blunt:

“My son, let the curse fall on me. Just do as I say.”

Our question tends to be, how could Yaakov deceive his father? Yet the real question is about Rivka. It was her plan, not his. How could she deceive her husband, deprive Eisav of his father’s blessing, and order Yaakov to commit an act of dishonesty? Yaakov on his own wouldn’t have conceived such a plan. He was an ish tam, “a simple, a man of pure integrity” But why did Rivka encourage him to act deceitfully?

There are three possible answers. The first is that she loved Yaakov over Eisav. Perhaps she wanted her beloved son to be blessed. But this is an unlikely answer. The avot and imahot are role-models. They were not driven by mere instinct or ambition. They acted with integrity. 

The second possibility is that she strongly believed Eisav was the wrong person to inherit the blessing. He had sold his birthright. He was a “hunter” and “a man of the field”, who did not fit the template of the Abrahamic brit. She knew that this was one of the reasons why God had already chosen Yitzchak over Yishmael. The third possibility is simply that she was guided by the oracle she had received prior to the twins’ birth: “Two nations are in your womb, and two peoples...one will be stronger... and the older will serve the younger.” Yaakov was the younger son, destined to receive the blessing.

Possibilities two and three make sense, but only at the cost of raising a deeper question. Did Rivka share her thoughts with Yitzchak? If she did, then why did Yitzchak persist in seeking to bless Eisav? If she did not, then why not?

The Torah emphasises distance between Yitzchak and Rivka in every sense. When Rivka first sees him, Yitzchak is far away, both physically and mentally: meditating, deep in prayer. Then Rivka adds her own distance by covering herself with a veil. Yitzchak is also the most withdrawn of the avot. He rarely initiates action, and the Torah has no mention of any words spoken between the couple. This is also the man who was bound as a sacrifice, saved only at the last moment. Jewish mysticism connected him with gevurah, best understood as “self-restraint.” Perhaps the trauma of this affected his relationships. If Rivka felt unable to share the oracle she received and her doubts about Eisav’s suitability, this lack of communication could have led to the deception which brought about a whole series of tragedies. 

Rivka acts at all times out of the highest of motives. She holds back from troubling Yitzchak out of respect for his inwardness and privacy. She does not want to disillusion him about Eisav, whom he loves. She does not want to trouble him with her oracle, suggesting as it did that the two boys would be locked into a lifelong struggle. Yet the alternative – deception – is worse. This is the tragedy of her good intentions. Honesty is at the heart of strong relationships. Whatever our fears and trepidations, it is better to speak the truth than practice even the most noble deception.

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Around the Shabbat Table

Questions to Ponder

  1. Do you believe there are times when lying is acceptable? 
  2. Where else in the Tanach has someone lied - or deceived - for the sake of good? 
  3. If you were Rivka, what might you have done differently in this situation?

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Written by Sara Lamm

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After twenty childless years God answers Rivka and Yitzchak’s prayers. Her pregnancy is difficult, but she is told “two nations” are in her womb, and the younger will rule. Eisav is born first, followed by Yaakov (grasping Eisav’s heel). Eisav becomes a hunter, while Yaakov is a scholar. One day Eisav recklessly sells his birthright to Yaakov in exchange for some lentil stew.

Later, fearing for his life, Yitzchak presents Rivka as his sister in Gerar. He prospers, reopens his father’s wells and digs new ones.

Before Yitzchak’s death, he announces he will be giving Eisav a special blessing. Rivka disguises Yaakov as his brother so that they might deceive Yitzchak, and Yaakov receives the blessing instead. Eisav vows revenge and Yaakov flees to Charan. Meanwhile Eisav marries three wives.

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Philosophy of Rabbi Sacks

This week’s Parsha reminds us that in all our interactions with others, we must keep in mind the power of honest communication. Rivka has the best intentions, wanting to ensure Yaakov receives the blessing, but her choice to deceive Yitzchak instead of talking to him leads to many problems. Eisav vows to kill his brother for his actions that day, and Rivka realises Yaakov must flee. He finds himself working for Lavan for twenty years, and tricked into a marriage to Leah, which ultimately leads to Yosef’s enslavement in Egypt, and subsequently all of Bnei Yisrael’s enslavement.

All this pain begins with Rivka’s deception. Rabbi Sacks reminds us how important it is to speak openly and truthfully. Honesty builds trust and helps avoid misunderstandings. And trying to protect someone with silence and tricks often causes more harm than sharing the truth.

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Two Truths and a Lie 


One player shares three personal facts. Two of these must be true, while one is made up. The other players listen carefully and try to identify the lie. After everyone has made their guesses, the person sharing reveals which statement was false. Then we move onto the next person to share their three facts.

This is a fun way to discover interesting facts about each other while testing everyone’s ability to spot a lie!

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A Story for the Ages

Once upon a time there lived an emperor who loved clothes more than anything. When two men came to his palace promising to make him the finest outfit anyone had ever worn, he was thrilled. But then they held out the fabric, and he couldn’t see anything in their hands. These tricky men explained, “Sire, the material is magical, and only the most special people can see it.” Excited to prove his worth, the emperor gave them bags full of gold. The men pretended to sew for days on end, promising he would be pleased with their final creation.

When the emperor went to try on his new clothes, he saw... nothing! But he didn’t want to seem foolish, so he praised the “invisible” outfit. His ministers, wanting to look special too, agreed with him, nodding and pretending they saw fine fashion. Soon, the whole kingdom was buzzing about how amazing the emperor’s new clothes would be. 

Finally, the day of the grand parade came. The emperor strutted down the main street in his “new clothes”. No-one mentioned that he was clearly wearing nothing at all. No-one wanted to admit they couldn’t see the clothes. The first people seemed impressed, and soon everyone agreed, clapping and cheering as he passed, waving their hands and nodding their heads.     

Then suddenly a voice rang out from the crowd. “But, but, but, he’s not wearing any clothes!” It was a child on her father’s shoulders, too young to worry about what others thought. The people gasped, but then they looked again at the emperor. As the whole town burst into laughter, he realised how foolish he’d been, and laughed loudest of all. Telling the truth helps everyone to see things clearly.

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Written by Rabbi Barry Kleinberg

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An introduction to this week's

When Rosh Chodesh (the new month) is on a Sunday, we read a special Haftara from the Book of Samuel – called “Machar Chodesh” (“Tomorrow is the New Moon”). This Haftara is read on the eve of Rosh Chodesh due to its opening line: “Then Jonathan said unto him [David]: “Tomorrow is the New Moon” (I Samuel 20:18).”  We will therefore explore this special Haftara as well as the usual Haftara read together with the Parsha of Toldot. 

The Book of Samuel, divided into I Samuel and II Samuel, tells the story of Israel’s transition from a loose confederation of tribes to a unified monarchy. It begins with the rise of Samuel, the last judge and a prophet, who is pivotal in leading the people of Israel. When they demand a king (and God agrees), Samuel anoints Saul as the first king, but Saul’s disobedience leads to his downfall. 

The narrative then follows David, who we meet as a young man and a lowly shepherd. The books tell  of his complex relationship with Saul (and his son Jonathan), his eventual kingship, the consolidation of his rule over Israel, and the establishment of David’s dynasty.

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In brief

I Samuel (Shmuel 1) 20:18-42  

At the funeral of Rabbi Sacks, Dayan Binstock quoted our Haftara: “And Jonathan said to him: ‘Tomorrow is the New Moon. You will be missed, for your seat will be empty.’” These words, from the opening of the Haftara for Machar Chodesh, can surely be applied back to Jonathan Sacks... Your seat is empty, your voice is missing.”   

For more than a year now, the Jewish people have been suffering greatly, and we have sorely missed the voice and wisdom of Rabbi Sacks. 

The Haftara tells of Jonathan and David’s plan to discover King Saul’s intentions toward David. Jonathan agrees to assess his father’s mood during the New Moon feast and David stays away. Saul becomes enraged at David’s absence, insults Jonathan, and seems to confirm his intent to kill David.

The next day, Jonathan secretly informs David through a prearranged signal involving arrows that David must run away. Then Jonathan and David meet in secret, reaffirm their deep friendship and covenant, and part ways with great sorrow, not knowing when they will meet again. David’s seat may be empty for a very long time.   

In the narrative of Parshat Toldot, Yaakov is also warned to flee, but it is his own brother he must run from, due to an act of disloyalty, and growing animosity between the two men. Jonathan and David’s love and loyalty amidst the growing threat from Saul paints a clear parallel and contrast to the relationship between brothers Eisav and Yaakov.

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A summary

Regular Haftara for Toldot - Malachi 1:1-27

God expresses His love for Israel, contrasting His treatment of Israel with that of Edom, whom He has rejected. Despite their chosenness, the people of Israel have shown disrespect toward God, particularly through the priests who offer impure and blemished sacrifices, violating the covenant. God rebukes the priests for their negligence and failure to honour Him properly, warning them of consequences if they do not reform. 

The passage emphasises the importance of reverence in worship and the role of priests as teachers of God’s laws. God also calls for sincere devotion and integrity in upholding His covenant. 

Rabbi Sacks set out the different roles of the priest and the prophet as follows: “The key words in the vocabulary of the Kohen [priest] are kodesh and chol, tahor and tamei, [meaning] sacred, secular, pure and impure. The key words in the vocabulary of the prophets are tzeddek and mishpat, chessed and rachamim, [meaning] righteousness and justice, kindness and compassion.”  

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  1. What do you understand about the roles of the Priest and the Prophet from the Rabbi Sacks quote? 
  2. Why do you think the Priests are singled out to be teachers?
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Tanach Connections

At the beginning of the Haftara, Malachi tells us that even though Yaakov and Eisav are brothers, their lifestyles could not be more different. This confirms the story we find in this week’s Parsha of Toldot in which we are told: 

“Yitzchak who had a taste for wild game, loved Eisav, but Rivka loved Yaakov.” (Bereishit 25:28) 

Rabbi Sacks expounds on the difference between the twin brothers, and how the younger brother (Yaakov) was the one to gain the birthright, the firstborn blessing, and the right to carry on the covenant first made by God with Avraham and then with Yitzchak. He notes, “The blessing had to go to Yaakov. If you had two sons, one indifferent to art, the other an art-lover and aesthete, to whom would you leave the Rembrandt that has been part of the family heritage for generations?” 

Yaakov was closely bonded with Eisav, but ultimately he was not the chosen son, or father of the Chosen People, for he did not carry the family values inherent to the one who would take on this role.        

The Haftara then comes to teach us: “Eisav is Yaakov’s brother; yet I have accepted Yaakov and rejected Eisav.” (Mal. 1:2-3). 

This idea of rejection, and the familial connection, is reflected in the Haftara, in the prophet’s words relating to Edom (“Eisav - that is Edom” see Bereishit 36:1) who took advantage of Judah’s weakness. 

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Putting the Prophets into Context

The Book of Malachi, the final book of the Twelve Minor Prophets, addresses the spiritual and moral decline of the Israelites after their return from exile. 

Malachi, speaking on behalf of God, rebukes the people for their lack of faith and improper worship, including the priests for offering blemished sacrifices and the people for neglecting tithes and offerings. He also condemns social injustices like divorce, intermarriage, and dishonesty. 

Malachi calls to the people to do teshuvah (introspection and repentance) and emphasises God’s enduring love for Israel, promising that those who remain faithful will be blessed.

The book concludes with a prophecy of the coming “day of the Lord,” when God will send Elijah the prophet to prepare the way for a time of judgment and renewal. 

Rabbi Sacks talks about Malachi, the last of the Prophets, who sees the Kohen as the arbiter of peace among the people of Israel ("My covenant was with him of life and peace . . . He walked with Me in peace and uprightness, and turned many from sin." Malachi 2:5-6)

As Rabbi Sacks explains, "Malachi is talking about priesthood in general" but the Sages use this as a prooftext that "the historical figure of Aaron" was the symbol of peace among the people during his lifetime. (Between Truth and Peace)

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“It may be that Isaac loved Esau not blindly but with open eyes, knowing that there would be times when his elder son would give him grief, but knowing too that the moral responsibility of parenthood demands that we do not despair of or disown a wayward son.”


Why did Isaac love Esau?,
Toldot, Covenant & Conversation from the ‘Lessons in Leadership’ series

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Do you think that social justice plays an important role in your religious life? 

Have you done anything recently that you would consider part of the mitzvah of tikkun olam (fixing the world)?

Covenant & Conversation Family Edition

Written as an accompaniment to Rabbi Sacks’ weekly Covenant & Conversation essay, the Family Edition is aimed at connecting teenagers with his ideas and thoughts on the parsha.

With thanks to the Schimmel Family for their generous sponsorship of Covenant & Conversation, dedicated in loving memory of Harry (Chaim) Schimmel.

“I have loved the Torah of R’ Chaim Schimmel ever since I first encountered it. It strives to be not just about truth on the surface but also its connection to a deeper truth beneath. Together with Anna, his remarkable wife of 60 years, they built a life dedicated to love of family, community, and Torah. An extraordinary couple who have moved me beyond measure by the example of their lives.” — Rabbi Sacks

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