Toldot: What Was Isaac Thinking?

It is the question we all have: What was Isaac thinking? Why must we endure reading Parshat Toldot every year with the discomfort of knowing our forefather Isaac favored our [Not] forefather Esau over our forefather Jacob? How can Isaac, one of the three sacred, holy, and wise founders of the Jewish nation, have overlooked Esau’s faults when they were so apparent from the get-go? The Torah tells us:

“And the youths grew up, and Esau was a man who understood hunting, a man of the field, whereas Jacob was an innocent man, dwelling in tents. And Isaac loved Esau because [his] game was in his mouth, but Rebecca loved Jacob.”

Despite Isaac’s being hard of seeing, there are clearly observable differences. There was something Isaac loved about Esau, something different; something unique. Knowing that Esau was the hunter in the field and Jacob was the innocent, studious one, the question begs for an answer: why? Why did Isaac prefer Esau?

This is all the more disturbing when we see that at least Rebecca “got it” and preferred Jacob. Things become even more disturbing. Why didn’t Rebecca alert Isaac to the facts? Why didn’t Rebeca take Isaac aside one day and whisper in his ear? She didn’t need to make Isaac dislike Esau; all she needed to do was to tell him that Jacob was the good guy.

The frustration becomes magnified when reading about how little this all meant to Esau:

“Now Jacob cooked a pottage, and Esau came from the field, and he was faint. And Esau said to Jacob, “Pour into [me] some of this red, red [pottage], for I am faint”; he was therefore named Edom. And Jacob said, “Sell me as of this day your birthright.” Esau replied, “Behold, I am going to die; so why do I need this birthright?” And Jacob said, “Swear to me as of this day”; so he swore to him, and he sold his birthright to Jacob. And Jacob gave Esau bread and a pottage of lentils, and he ate and drank and arose and left, and Esau despised the birthright.”

Why would Isaac want to entrust the gift of carrying the Abrahamic legacy to Esau, when Esau valued it less than a bowl of soup?

As a young Yeshiva student, I was very blessed to have Rabbi Aharon Schachter, Dean, and Rosh Yeshiva of Yeshiva Rabbi Chaim Berlin. As Shabbat was drawing close to its conclusion, students from his Yeshiva and myself would huddle around his Shabbat table in his home, eat the third meal (se’ uda shlishit), sing medlies that touch the heart and soul, and bend forward attentively to hear the rabbi’s insights on the weekly Parsha. It was one of my first week there. It was Parashat Toldot, here is some of what the rabbi shared on this topic.

Abraham had two sons, Isaac and Ishmael. One was chosen, one was “unchosen”. At some point, the process of having “chosen” children and “unchosen” children would have to come to an end. There would have to be a recognition that all children, albeit different, have a place within the Abrahamic trajectory. There would have to be a recognition that in our pursuit of spirituality, there is a plurality of strengths different people bring with them and that those strengths are to be cherished and valued. This is what happened with Jacob and the twelve tribes. With the twelve tribes came the recognition that more than one child can be the heir to the family’s covenant and to Abraham’s blessings. This is why the brothers were so angered by Joseph’s claim to any kind of closeness; up to that point being chosen meant that others were unchosen, putting the brothers at an existential spiritual threat.

When Isaac saw Jacob and Esau, he did see very different people in front of him. Isaac did not ignore Jacob’s merits. Isaac thought Jacob and Esau can partner and use each their own qualities. When Moses blesses the different tribes, he says: “Rejoice, Zebulun, in your departure, and Issachar, in your tents. )Deuteronomy 33:18) There is a clear division of labor here. Zebulun is the one who does business, practices Judaism in the public sphere, and supports his brother. Issachar other the other hand spends time practicing intense spirituality while studying in the tent. This was the division Isaac thought of for his sons Jacob and Esau.

It is also hard to imagine Isaac forgot the harsh way in which he saw his own brother, Yishmael, being banished from having a role in the family trajectory. This is something Isaac surely did not wish upon his own son.

So why did Isaac choose Esau to be the “chosen” one and not give his sons equal privileges? The key to this can be found later in the Parsha. After the famous episode of Jacob “stealing” the blessings from his brother Esau by donning his brother’s clothing and Esau wanting to kill him, Isaac quickly summons Jacob over.

“And Isaac called Jacob and blessed him, and he commanded him and said to him, “You shall not take a wife of the daughters of Canaan. And may the Almighty God bless you and make you fruitful and multiply you, and you shall become an assembly of peoples. And may He give you the blessing of Abraham, to you and to your seed with you, that you may inherit the land of your sojournings, which God gave to Abraham.”

While “the blessing of Abraham” refers here to the land of Israel, it also refers to another thing. Abraham was not a man of the book or the tent. Abraham was someone who brought God’s name out there into the world. His work was accomplished through worldly conversations, engagement with the masses, and an understanding of human nature.

When Isaac sees the differences between his sons, he comes to a very reasonable conclusion: Jacob can be a man of the book, while Esau can bring the message of Abraham out the people. He does not need to choose one and “unchoose” the other. Esau will be the one to carry out the full work of Abraham while Jacob will continue to inspire and study. The ideal of Judaism is not a faith that is to be constrained to the halls of synagogues or the pages of books, Judaism is a faith that is to be found in the marketplace, the street corner, and the field. It is a religion of Mitzvot, practice.

When God assures us we will be rewarded for observing His commandments in the land of Israel he tells us (Deuteronomy 11) we should do so “in order that your days may increase and the days of your children, on the land which the Lord swore to your forefathers to give them, as the days of heaven above the earth.” Heaven on earth here is not just a metaphor; it is the sum total of what Judaism is about, creating a heaven on earth.

This would all be true of Esau’s outdoor activities were limited to being very active and engaged. What Isaac did not know is that Esau was not merely an outdoorsy type for person; when Esau was out of home his actions were outright immoral and abhorrent.

This was not simply an oversight; Esau played an active role in facilitating it. The verse states, “the youths grew up, and Esau was a man who understood hunting.” Rashi explains, “who understood hunting: [Esau knew how] to trap and to deceive his father with his mouth and ask him, “Father, how do we tithe salt and straw?” His father thereby thought that he was scrupulous in his observance of the commandments (Tanchuma, Toeldoth 8). Esau would ask his father questions about implementing Jewish law in day to day life. These were not questions presented by Jacob; Jacob was sitting in the tent. Bringing Judaism into the real world did not seem like Jacob’s forte. The only problem was it was all fake. Esau was showing off something he didn’t have. “Isaac loved Esau because [his] game was in his mouth” Rashi explains, “with Esau’s mouth, for he would entrap him and deceive him with his words. — [From Tanchuma, Toledoth 8]” The one who was really being hunted here was Isaac. In theory, Isaac was right, Esau would make a better candidate to be the one and carry one Abraham’s legacy into this world. The only problem was that Esau was faking it all.

At the end of the Parasha, once Isaac recognized that, after Esau revealing himself as violent and vengeful, he willingly continues to bless Jacob with all of the blessings. There is no room for murderously deceitful behaviors in the Abrahamic faith. While Esau is out of the game, there is a powerful lesson to be learned from the original choice Isaac made. The blessings of Judaism are not to be contained to one place; there are to be spread all over. When describing the virtues of King Solomon, aka Kohelet, the book of Ecclesiastics states: “And more [than this], Koheleth was wise, he also taught knowledge to the people; he listened and sought out, he established many proverbs.” While other intellectuals and elites looked down at and despised “the masses”, Judaism always saw the highest virtue in being able to convey wisdom to many and to bring down heaven to earth.

Shabbat Shalom!

About the Author
The writer is a rabbi, writer, teacher, and blogger ( He is the president of EITAN-The American Israeli Jewish Network and lives with his wife in New York City.
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