Toldot: Isaac’s Two Sons and the Challenges of Parenting

Rabbi Daniel Z. Feldman

The very dramatic first section of the Torah portion of Toldot begins with the word that gives the portion its name, and also sets the tone for much of what we will read about. “These are the toldot of Isaac (Gen.25:19)” – a word that can be translated a number of ways. Literally, it means “these are the descendants” of Isaac, but it can also be read as “this is the story of the life of Isaac.” Those two themes, biography and progeny, are deeply interconnected in the portion. We read about the children of Isaac, but we also read about the legacy of Isaac, and about how his sons define and carry – or fail to carry – that legacy.

Legacy is, in fact, the next note the verse sounds. After “Isaac, the son of Abraham,” the Torah adds, “Abraham begot Isaac” – a seemingly repetitive statement. Many commentaries suggest that the message is that Isaac followed in Abraham’s path, carried on his mission and legacy. The question of who, among Isaac’s descendants, would in turn carry on that mission becomes one of the major themes of this section and of the entire portion.

The text tells us that Isaac and Rebecca at first struggle to have children, and they pray to God that this be resolved. Their prayers are answered, and they are blessed with twins, already prophesied to be the ancestors of different nations. That future is reflected in their personalities. The Torah (25:27) describes Esau as “a man who knows hunting, a man of the field,” while Jacob is described as “a simple man, dwelling in tents,” a very different kind of person.

The difference between them became, in the eyes of Rabbi Samson Raphael Hirsch, the basis for a sharp critique of Isaac and Rebecca’s parenting. Among other points, Rabbi Hirsch suggests that one source of their later problems was that, despite the obvious differences between Jacob and Esau, they were given the same education – in violation of the wisdom of the verse in Proverbs, “Train a child according to his way,” which teaches that different personalities and inclinations require different styles and approaches.

That reading has great power, and it speaks to a real and urgent truth about education. But it is also possible to read the verses somewhat differently.

It is noteworthy that the Torah tells us: “Isaac loved Esau, because game was in his mouth; but Rebecca loves Jacob (25:28).” Each parent, the text tells us, has a favored child, so to speak. Rebecca’s love for Jacob is easily understood given his righteous personality. But Isaac’s love for Esau is introduced with a troubling explanation: “because game was in his mouth.” On the surface, this sounds as if Isaac was susceptible to being won over by bribery, by what Esau put on the table for him.

On a straightforward reading, Isaac seems to emerge looking rather naïve – either bribed or duped. The Midrash, followed by some later commentators, even portrays Esau as consciously manipulating his father with pious-sounding questions and carefully presented food. Rabbi Hirsch takes those traditions seriously and criticizes both parents. It is hard not to feel the force of that critique.

And yet, many later writers sensed that this picture is incomplete. The founding Rosh Yeshiva of Kerem B’Yavneh, Rabbi Chaim Yaakov Goldvicht, and its mashgiach, Rabbi Avraham Rivlin, both suggest a very different way of reading Isaac’s perception of his sons. It is not that Isaac understood Esau to be purely materialistic and devoted to the hunt, and Jacob to be purely spiritual and devoted to study. Rather, Isaac saw Jacob as only spiritual – a person of the tents of Torah – while he saw in Esau a certain capacity to bring together the spiritual and the material worlds. Precisely as “a man of the field,” Esau might, in Isaac’s view, be better positioned to carry the mission of the Patriarchs into the broader world. If so, Isaac’s preference did not stem from being taken in by a plate of venison, but from a considered judgment about what the mission required.

Another important nuance emerges from the language the Torah uses to describe the parents’ love. Rebecca is described as one who “loves Jacob,” in the present tense, suggesting an ongoing, almost instinctive affection. By contrast, the verse says that “Isaac lovedEsau,” in a way that may imply a more active, deliberate stance. Isaac chose to love Esau. He recognized his more dangerous and materialistic tendencies, and precisely for that reason he directed extra attention and affection toward him. He saw a need to guide Esau’s growth, to nurture and develop the spiritual part of his personality so that his worldly inclinations would be merged with a higher purpose.

If so, this already diverges significantly from Rabbi Hirsch’s interpretation. Rather than presenting one undifferentiated educational approach for both boys, the Torah may be hinting at two distinct educational strategies: Rebecca, with a natural and ever-increasing love for the more obviously righteous son; Isaac, with a consciously cultivated love for the more complicated child.

Rabbi Shmuel Berenbaum, in Tiferet Shmuel, points in a similar direction. He suggests that Isaac fully understood Esau’s general nature, and was not blind to his profound flaws. What caught Isaac’s attention was a specific element embedded within Esau’s very attempts to deceive him. The Talmud understands the phrase “game was in his mouth” as alluding to Esau’s habit of asking Isaac elaborate halachic questions in order to appear righteous. But, Rabbi Berenbaum notes, even a dishonest attempt to appear righteous can reveal a genuine desire to impress a parent, to be seen as good in the eyes of someone one respects. That desire, misdirected as it was, testified to a latent instinct that could be harnessed for authentic growth.

Accordingly, Isaac “loved Esau” in the sense that he focused his active, intentional love on that kernel of aspiration. He saw a son who, however wayward, still wanted his father’s approval. Isaac directed his energy to that point of connection, hoping that it could be nurtured and expanded until it transformed Esau’s inner life.

Seen this way, the verse that has long made Isaac look misled may, in fact, be an expression of a deeply sophisticated parental strategy. Isaac is not a naive old man, either bribed or duped; he is a parent making the difficult choice to invest extra love where the risk is greatest and the need is most acute. Rebecca, for her part, may be described as “loving Jacob” in the sense that her love kept growing – some commentators even read the present tense as indicating that the more she heard of Esau’s behavior, the more she reinforced and encouraged Jacob’s righteousness.

This entire tension between parental responsibility and children’s choices is echoed in another place in Jewish life: the blessing traditionally recited by a father at his son’s bar mitzvah, “Blessed is He Who has now exempted me from punishment on account of this child.” (Rama OC 225:2). Notably, the Midrash Rabbah associates this practice with the verse that relates that Jacob and Esau “grew up” (25:27).

The classic halachic authority Magen Avraham explains that, before the child reaches the age of thirteen, the father is held accountable for some measure of the child’s sins, because he is obligated to educate and guide him. Once the child becomes personally obligated in the commandments, the father is “released” from that direct responsibility.

A different commentary, Etz Yosef, suggests another layer: before thirteen, a child’s tendencies are not yet fully visible or fixed. That is precisely the window in which parents must be especially attentive, trying to discern who this child is and to guide those emerging tendencies in the right direction. The blessing, on this view, marks the end of that unique, formative stage.

A third approach, attributed to the Baal Shem Tov, adds yet another dimension. Before bar mitzvah, a child may need to hear things primarily in the language of reward and punishment: “If you do this, it will be good for you; if you do that, there will be consequences.” After thirteen, the parent is freed – and perhaps obligated – to speak in a more mature vocabulary, appealing to responsibility, meaning, and inner conviction rather than to simple incentives.

All three interpretations circle around the same core: parents are responsible to educate, to notice who their children are, to invest effort, love, and thoughtful guidance. But ultimately, children grow into their own moral independence. The blessing is not a declaration of indifference, but a recognition of the limits of control.

This brings us back to Isaac. So why, we might still ask, did he “fail” with Esau?

The beginning of the portion itself complicates that question. Even before the boys are born, Rebecca is told that “two nations are in your womb” and that “the older shall serve the younger.” The rivalry between Jacob and Esau, and the distinct destinies they represent, are woven into the fabric of the narrative from the outset. The Torah does not present the outcome as the straightforward product of parenting success or failure. It is, in some deep way, part of the divine script of history.

Moreover, Esau himself is not without redeeming qualities. The Sages famously highlight his extraordinary fulfillment of the commandment to honor father and mother. Whatever else he became, there was a real relationship with his parents, a genuine connection sustained over years. Isaac’s efforts were not entirely wasted. Even where a child’s larger path diverges painfully from what parents had hoped, strands of the legacy remain: habits of respect, moments of loyalty, residual awareness of the values that were taught.

“These are the toldot of Isaac” thus signals not only a list of names, but a complex, often painful, and yet profoundly instructive story of legacy. Isaac, the son of Abraham, indeed begets Isaac, the one who carries forward Abraham’s mission in his own distinctive way. Isaac then faces the agonizing task of trying to transmit that mission to two very different sons – one transparently righteous, one deeply conflicted. He and Rebecca do not simply repeat a single educational formula; they each respond, in different ways, to the different children in front of them. They love, they guide, they hope, and they do so under the shadow of a destiny that is not entirely in their hands.

For parents and educators, the portion of Toldot offers a sober and consoling message. We are commanded to train each child “according to his way,” to notice, to differentiate, to choose love actively where it is hardest, and to reinforce goodness where it appears. We are indeed responsible for effort, not for outcome. Isaac does not stand here as a cautionary tale of parental failure, but as a model of the complexity, the courage, and sometimes the heartbreak of a life devoted to building a legacy among children who are, ultimately, their own people.