November 6th, 2021: Parashat Toldot – Unique Brothers

This week’s parashat is taken from Genesis 25:19—28:9. Listen in as David discusses the meaning of "Toldot" and the introduction of Isaac's genealogy.


Follow along in the AUDIO PODCAST, by clicking on the play button below, and reading along with the notes, as you listen to today's Parashat:




Genesis 25:19—28:9


In this week’s Torah portion, we are introduced to the offspring of Isaac, hence the name of the parashah – “Toldot” meaning “offspring” or “generations”. Most notably, we are introduced to a brotherly rivalry that began within the womb of their mother and has lasted till this day – that of Jacob and Esau. For anyone who knows the story, Jacob is associated with righteousness, while Esau with unrighteousness, yet all throughout this parashah, we see neither quality completely revealed in either of the men. Certainly, within this parashah we see propensity by Jacob toward righteousness and Esau toward unrighteousness. But this brings into question – were these propensities set in stone from the womb? Did it have to turn out this way? Moreover, how is it that such a dichotomy of offspring could emerge from such righteous parents as Isaac and Rebekah? The simple answer is that just because Jacob and Esau were different in many ways didn’t pre-determine that one should be good and the other evil. What we ultimately learn is that their upbringings and environments had a major influence on how they turned out, and their parents played an important role in helping shape their paths.


We open up the parashah in Genesis 25:19 to these words: “And these are the offspring of Isaac son of Abraham – Abraham begot Isaac.


וְאֵ֛לֶּה תּוֹלְדֹ֥ת יִצְחָ֖ק בֶּן־אַבְרָהָ֑ם אַבְרָהָ֖ם הוֹלִ֥יד אֶת־יִצְחָֽק׃


We read on to learn of the difficult circumstances surrounding the birth of these offspring of Isaac. Rebekah was barren, and it wasn’t until Isaac entreated Hashem that his wife conceived. Yet, even then, the circumstances became just as difficult. It says in Genesis 25:22-23: “And the children ‘crushed’ within her… And she went to inquire of Hashem. And Hashem said to her: ‘Two nations are in your womb; and two regimes from your insides shall be separated; and one regime shall become strong from the other regime, and the elder shall serve the younger.” This ‘crushing’ is characterized as smashing or shattering to the point of destruction. What was going on in her womb was anything but normal – there was a struggle going on within her. This tells us that the struggle that went on between Jacob and Esau in their adult years began in the womb. At the very least, what we must take from this is that Jacob and Esau were very different from each other from the womb.


We gain more insight into their differences in Genesis 25:27 where we read: “The lads grew up and Esau became a man who knows trapping, a man of the field; but Jacob was a wholesome man, abiding in tents.” It is in this verse that we begin to see that the differences of the two brothers were taking form in their lives. Esau, on one hand, was a man “who knows trapping”, while Jacob was “a wholesome man”. Moreover, Esau was “a man of the field”, while Jacob “[abode] in tents”. A basic interpretation speaks of Esau as a hunter, and Jacob as having “soft skills” by dwelling in tents, but there’s more going on here. On a deeper level, it is telling us that Esau – “a man of the field” – was becoming a man knowledgeable in the ways of the world, and he knew how to use his skills to influence, hence the use of the word “trapping”. It says in the next verse (Genesis 25:28): “Isaac loved Esau for trapping was in his mouth; but Rebekah loved Jacob.” There is a dual meaning here: 1) If “in his mouth” is referring to Isaac, Esau used the trappings from his hunting expeditions to gratify his father; and 2) If “in his mouth” is referring to Esau, it means that Esau spoke the words he knew his father wanted to hear, i.e., he knew how to “influence” his father with words.


On the other hand, Jacob – a man “abiding in tents” – sought knowledge and wisdom, particularly in the ways of Hashem, hence his “wholesomeness”. Who did Jacob learn from? For one, notice that “tents” is plural. He certainly could have learnt from his parents – Isaac and Rebekah, but there is potentially another he could have learnt from – his grandfather, Abraham, as Abraham would have still been alive at the time of his adolescence. [Note: At the time of Sarah’s death, Abraham was 137 and Isaac was 37. At the age of 60, Isaac fathered Jacob and Esau (and Abraham would have been 160). Since Abraham died at the age of 175, the two boys would have been 15 years old.] If this is the case, Jacob would have had a great teacher and mentor in his grandfather. Yet again, all we are learning here is that the two brothers’ characters, qualities, skill sets and volitions were uniquely different from each other.


We then see their differing valuations for the birthright. We read later on that Jacob boiled a stew, and Esau came in from the field exhausted. Esau, in his exhausted state, asked for some of the stew, and in return, Jacob said “Sell, as this day, your birthright to me.” Esau said, “Look, I am going to die, so of what use to me is a birthright?” Ultimately, Esau sold his birthright to Jacob, and it says in Genesis 25:34: “… and he [Esau] ate and drank, got up and left; and Esau belittled the birthright.


What was the significance of the birthright? The first thought is that it was connected to the right of their father’s inheritance, but what son in his right mind would give up his firstborn right to inheritance? In this context, why would Esau belittle his birthright? Again, it doesn’t make sense that it speaks of financial inheritance, for we know that Isaac became wealthy through inheritance from Abraham. Rather, it is more likely that the birthright that Jacob purchased from Esau was the right to the future inheritance of the Land promised by Hashem to Abraham. If this is the case, it has more to do with carrying on Hashem’s promise to Abraham rather than any sort of financial inheritance, and Jacob bought it out of honour to Hashem’s covenant with Abraham, while Esau belittled it because he saw no value in it. Thus, it makes more sense why Esau would belittle the birthright. While Jacob deployed crafty means to attain the birthright, it was done with the right intention to carry on the promise and legacy of Abraham.


We next see Esau’s poor choice in wives. In Genesis 26:34-35, we read: “When Esau was 40 years old, he took as a wife Judith daughter of Beeri the Hittite, and Basemath daughter of Elon the Hittite; and they were a provocation of the spirit to Isaac and to Rebecca.” Interestingly, Esau got married at the same age that his father was married (the age of 40). However, he wasn’t content to take one wife but rather he took two. Furthermore, he chose Canaanite wives which was in direct contradistinction to his grandfather’s command that Isaac, his father, not find a wife amongst the Canaanites. Esau certainly knew what he was doing, and this points to his ability to make misguided decisions, and it was ultimately a rebellious act.


We then read of Jacob’s craftiness in stealing the blessing of the firstborn. We read in Genesis 27 that Isaac had become old and that he summoned Esau, his older son, to catch game for him so that he could bless him before he died. We read that Rebekah was listening, and since Isaac’s eyesight was poor, she dressed Jacob up in Esau’s clothing, covered him with goat skin and cooked him the delicacies that he loved so as to resemble Esau. Jacob followed his mother’s orders and deceived his father into giving him the firstborn blessing. Again, this was done very deceptively – sure, it was planned by Rebekah, but certainly Jacob complied. Remember, before Rebekah gave birth to her sons, Hashem told her that “the elder shall serve the younger”, and this must have given her impetus to ensure that her favourite son, Jacob, received the firstborn blessing. Yet, was this done with an evil motive? Certainly not! Rebekah was protecting the promise from Hashem for her favourite son – the younger – that the elder shall serve the younger. Similar to before, the motive was good and was done to ensure that Isaac, blinded by his stomach, didn’t give the wrong blessing to the wrong son. This may have been a presumptuous act on the part of Rebekah, but she was doing what she felt she had to do to protect the word that Hashem had given her, albeit to protect her favourite son, Jacob.


One last episode is when Isaac and Rebekah sent Jacob to Paddan-Aram to find a wife. It says in Genesis 28 that Esau saw that his parents sent Jacob off to find a wife in Paddan-Aram, and that Isaac had commanded Jacob: “You shall not take a wife from among the daughters of Canaan”. It goes on to say that because Esau saw that the daughters of Canaan were evil in the eyes of Isaac, he took the daughter of Ishmael as a wife in addition to his wives. Here, Jacob obeyed his parents and went north to Paddan-Aram. Esau, on the other hand, opted to go to the south, to take as wife the daughter of Ishmael. Was this yet another act of rebellion?


All through these instances, one element rings true – none of these actions by either Jacob or Esau could be classified as an outright righteous act or an unrighteous act. You can certainly say that they highlighted Jacob’s propensity towards righteousness and Esau’s propensity towards unrighteousness. We also see the craftiness employed by Jacob to accomplish deeds done with good intent, and then we see outright acts of rebellion employed by Esau that beg to question: Why?


Here we have Jacob who was naturally geared towards the ways of Hashem – he preferred the learning environment, and as a result, he was inclined towards obedience and honour for his parents and for the ways of Hashem. Then we have Esau who preferred to spend his time in the field, pursuing after the ways of the world. His inclination was towards rebellion and following his own path. Yet, you would assume that the two brothers had a similar upbringing, and that their parents would have poured into their lives the righteous values that were inherent in their lives. How in the world could this happen with Esau?


This is the point where we must look at his environment – “the field”… “the ways of the world”. This in itself is not the problem. Sure, the world can be a dangerous place, full of sinful dangers and pitfalls. Yet, one who is well-grounded in the ways of Hashem will not fall into these dangers because of their solid foundation in Hashem. We see this in the life of Abraham – he was firmly established in Hashem, and as a result, was able to traverse the world with ease. We also see this later on in Jacob’s life, as he had to face many trials in his life and within his family (due in part to his deceitful acts), but because of his foundation in Hashem, he remained firm. Esau did not appear to have such a foundation, and this was either a result of his lack of interest in learning the ways of Hashem or perhaps the inability of his righteous parents to influence him and his inclination towards the world.


Esau’s inclination towards the world wasn’t in itself to be frowned upon, it just revealed that his environment of choice was different than what his father Isaac, his mother Rebekah, or his brother Jacob, were accustomed to. Isaac was protected as the son of promise from Hashem. He wasn’t allowed to go with Eliezer to find a wife, and later on, Hashem disallowed him from going down to Egypt due to a famine in the land. Rebekah was a righteous woman plucked out from the midst of a pagan household at a young age to marry Isaac. And Jacob already had a natural inclination to dwell in tents, to remain close to home and to learn from his elders.


How is this any different than today in any given household of siblings? Very rarely is there ever a set of siblings that are similar in their inclinations. Typically, there is a mix – extrovert / introvert, scholar / tradesman, musical / non-musical, and so forth.


The fact of the matter is that the two sons differed notably from each other – from the womb. This was made clearer in their growth development as one preferred the field and the other, tents. Furthermore, each parent had a favourite son. As such, there was disparity in the household. As I said earlier, in this parashah, neither son could be distinguished clearly as righteous or unrighteous – that came later. However, their actions reflected their upbringings and environments. Again, they must have had similar upbringings from an early age. Yet, I can tell you from first-hand experience that it is very easy to pretend to be a good student and child on the outside, when in reality, there is a propensity to rebel within. The question is if Esau’s parents were able to pick up on this. The answer is doubtful as the rebellion started manifesting externally at a later age. Esau’s quality as “a man of the field”, a man chasing after the things of the world was a quality that Isaac and Rebekah do not appear to have had any experience with. And as such, they appeared ill-equipped to influence their son in just the right ways to support him in his volition suited for the environment that he was attracted to.


In no way am I blaming Isaac and Rebekah for how their son turned out. What I am merely pointing out is that Esau had an inclination in his life that his parents could not relate to, and as such, it is doubtful that he received the righteous support grounded in Hashem that he needed to empower him in his mission in this world. On the other hand, in no way am I defending Esau’s actions. At the end of the day, Esau was accountable for all that he did. He certainly dwelled in the camp of his father and mother for much of his life, and as such, had righteous influence close at hand. He had a choice in the matter in the adult years, and he made bad decisions that resulted in his drive toward unrighteousness. Moreover, at any point, he could have repented and returned back to the ways of Hashem. As a result, Esau’s descendants became a thorn in the side of the nation of Israel.


Perhaps with the right guidance and direction from both his parents, Esau could have been a great force for good in the world – especially from his early years. I believe Hashem gave Isaac and Rebekah two unique and discernible seeds to serve higher purposes in the rectification of this world. As Jacob and Esau carried uniquely inherent qualities that differentiated themselves in this world, this speaks strongly to each of their missions. Jacob went on to father the nation of Israel, eventually brought forth the righteous seed of Messiah Yeshua, who is the source of salvation for the world.


But what about Esau’s role? Remember, Esau was still of the seed of Isaac and Abraham and as such, he cannot be neglected. Remember his inclination – that of the field, while Jacob was of the tents. This suggests that the potential impact of Esau could have been grandiose compared to that of Jacob. However, Esau belittled his birthright, and remained in a state of rebellion and went on to father the rebellious nation of Edom. This, however, does not limit in any way the role that the descendants of Esau can still play in the world. Who are they today? There are a number of views as to who the Edomites are. This is a subject matter beyond the scope of this teaching, yet, the simplest answer is that they were dispersed and intermingled amongst the other nations, including Israel (the last reference we have in the Bible of an Edomite is the lineage of King Herod). For one thing, we can certainly identify them by their character traits – by their connection to the ways of this world and their rejection of the Jewish people. It is this staunch rebellious nature that led Hashem to reveal words of destruction for them through the prophets. As Obadiah 1:18 says: “The House of Jacob will be fire, the House of Joseph a flame, and the House of Esau for straw; and they will ignite them and devour them. There will be no survivor to the House of Esau, for Hashem has spoken.” Hashem’s dire response is a result of a continued state of rebellion and rejection of His ways by the House of Esau. Not only that, it is a judgment that is reserved for the End of Days and not anytime sooner, which means there is still hope. This means that there is the opportunity for redemption, reconciliation and rectification – to redeem their ways from the rebellious example set forth by their forefather Esau, to reconcile with Israel their brothers, and to ultimately do their part in bringing complete rectification to the world.


As an aside: Returning back to the name of the parashah “Toldot”, there is one final insight that I’d like to highlight. What is very fascinating about this word “תּוֹלְדֹת” “toldot” is that it is featured 13 times in Scriptures (from Genesis through to the Book of Ruth), and within those 13 references, there are four different spellings of the word. In its fullest spelling, the word features two “ו” “vav” letters (“תולדות”), and in its limited spelling, it features no “ו” “vav” letters (“תלדת”). What is the difference? On the surface, absolutely nothing, as the “vav” letters only serve as vowel points, hence, the translated meaning of the word remains the same. However, there is most certainly something else going on here.



There is a powerful message embedded here. In its full spelling (“תולדות”), the word is only featured twice. Interestingly, these two times are at the start and end of the word’s use in Scriptures – first, at the beginning in the creation story (Genesis 2:4 – “These are the ‘offspring’ / ‘generations’ of the heavens and the earth when they were created…”), and last, at the end of the Book of Ruth (Ruth 4:18 – “These are the ‘offspring’ / ‘generations’ of Perez… and Jesse begot David.”). In between these two points of Scripture are featured the limited or defective forms of spelling (“תלדת”, “תולדת”, “תלדות”). What does this mean? Before Adam and Eve sinned in the Garden, Creation was in a perfect state, and only through the seed of David – through the Messiah, through Messiah Yeshua – will

Creation be returned back to that perfect state.


And what about us today? From a parenting perspective, it is up to parents – and righteous parents at that – to leave an impactful influence grounded in love, instruction and discipline on their children. Yet, the typical belief by many parents is that through strict rules and zero tolerance, they will bring forth righteous children. As is often the case, this tactic has backfired, pushing the children towards a state of rebellion. On the other hand, being too lax with a child or not being able to properly connect with them – as we see in the case of Esau – can have similar consequences.


King Solomon wrote in Proverbs 22:6: “Train the youth according to his way; even when he grows old, he will not swerve from it.” The key words here are “train the youth according to his way”, as in, bring the child up in the necessary ways possible that will ensure that they walk along the straight path. There is never a “one-size-fits-all” method to train a child. Each child is so unique from each other, requiring unique methods to be employed in their upbringing. Parents must be discerning to see the good that Hashem has embedded in their children’s lives, and thrive to identify and extract that good essence to help the child overpower the allure of the wicked ways of the world. Overall, parents play such a pivotal role in influencing their children – the next generation – in the ways of Godliness and righteousness.


Jacob and Esau were unique brothers, different from each other in such unique ways. They were born to righteous parents, yet the question is whether their righteous parents could truly connect with them in the right ways. It is disheartening to see how Esau turned out, especially given his great potential to do good. At the very least, we need to take from this the importance of being righteous examples for our children, taking into consideration their unique qualities and dispositions. For only then will we be able to fine-tune the right instruction and discipline suited for them. There is never a guarantee that our children will honour and respect us as parents, but it is up to us as parents to do everything in our power to train up our children in the ways of righteousness. Amen.

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