When Isaac and Rebecca saw the behavior of the local Hittite women their son Esau had married,1 they directed their other son (Esau’s twin) Jacob to choose a wife from amongst his cousins.2 Jacob dutifully left his hometown of Beersheba and traveled to Haran in Upper Mesopotamia (today, Northwestern Iraq), where he stayed for 20 years, having married two of Laban’s daughters—first Leah, then Rachel.

All of this did not go unnoticed by Esau. He well understood that his parents were not particularly enamored by his choice of women, and decided to act:

Esau saw that Isaac had blessed Jacob and sent him away to Padan Aram, to take himself a wife from there, and that when he blessed him, he commanded him, saying, “You shall not take a wife of the daughters of Canaan.” … Esau saw that the daughters of Canaan were displeasing to his father Isaac. So Esau went to Ishmael, and he took Machalat, the daughter of Ishmael, the son of Abraham, the sister of Neba’ot, in addition to his other wives as a wife.3

What are we to make of Esau’s action to marry a new woman? Was it a sincere effort to put things right? Had Esau changed his ways?

Rashi doesn’t seem too convinced:

He [Esau] added wickedness upon his wickedness, for he did not divorce the first ones [wives].

Right or Wrong?

We may surmise from this that his new choice of wife was no better than his previous choices. As proof, Rashi cites the fact that his new wife was “in addition to his other wives.” If he had really changed, why did he stay with his wicked wives who were causing his parents so much anguish?

There is, however, a significant problem with this. Rashi himself comments later that the name of Esau’s new wife, Machalat, signifies forgiveness from sin: “Therefore she was called Machalat, because [Esau’s] sins were forgiven.”4 Rashi seems to be contradicting himself: If Esau’s sins were forgiven because he married Machalat, how does that fit with the description of the new marriage as more of the same wickedness?

Indeed, the Midrash provides two conflicting opinions about Esau’s new marriage. According to Rabbi Joshua ben Levi, Esau had genuinely decided to mend his ways. But according to Rabbi Eliezer, the next wife was just “a pain on top of another pain, a thorn to complement another thorn.”5 Rashi seems to side with Rabbi Joshua when explaining the noble character of the new wife, Machalat, yet he appears to adopt the more cynical view of Rabbi Eliezer by discrediting Esau’s actions.

So, let’s clear this up: was she a good wife and Esau was righteous, or was she a bad wife and Esau was maintaining his wickedness?

It’s the Thoughts that Count

In brilliant fashion, the Rebbe shows that Rashi is saying something quite different to what we have been assuming till now. Pay close attention to the brief text of Rashi, and you will see that he does not imply that the new wife was anything other than good. The wickedness was not in whom Esau chose to marry, but in his intentions.

In fact, logic dictates that Esau’s new wife was a good person. The whole reason Esau married someone new was because he knew that his parents disapproved of his previous marriages, and with this new marriage he hoped to win their approval. That is why this time around he married his own cousin, Abraham’s granddaughter. If Machalat was a wicked woman like his existing wives, how would that have pleased Isaac and Rebecca? It therefore stands to reason that she was a marked improvement on his previous choices.

But if Machalat was a good woman, where was the wickedness?

You see, Esau was very sly. Everything he did was calculated and manipulative. He always had an agenda. If it took marrying a good wife to continue his misleading games, he was more than willing to take that approach. Esau married a good woman? Sure, but only as a way to maintain his ongoing manipulation.

A Serial Manipulator

Let’s go back to Esau’s first marriage:

Esau was forty years old, and he married Judith, the daughter of Beeri the Hittite, and Basmat, the daughter of Elon the Hittite.6

Why are we told how old he was at the time? According to Rashi:

Esau was compared to a swine… This swine, when it lies down, stretches out its [split] hooves, as if to say, “See, I am a clean (kosher) animal.” Esau likewise robbed and plundered, and then pretended to be honorable. During the entire forty years, Esau kidnapped wives from their husbands and violated them. When he was forty years old, he said: “My father married at forty; I too will do the same.”

His first marriage was an act, a show. It was insincere, intended only to dupe his parents into thinking he was doing the decent thing. In reality, Esau was a crass and violent womanizer. He made a big show of deciding to finally “settle down into married life,” but only because he believed it would make him look a whole lot better. We know the whole thing was a fake, because just look at who he married — those women gave his parents endless heartache.

Now Esau was at it again – but with a twist. He realized that his parents were distressed about his wives, so he decided to deceive them by marrying a good woman, hoping that he would again be able to mislead them about his character.

Good Wife, Bad Marriage

There is no problem at all with Rashi saying that Machalat was righteous, and that her name implied forgiveness of sins, for indeed she was pious and noble. The same, however, could not be said for Esau, who used his marriage to this wonderful woman to further his deceit and obfuscation. Esau was a hypocrite and remained a hypocrite.

There is an important lesson in all of this. Esau’s deception would have been very hard to uncover. After all, he married a genuinely good person – Abraham’s granddaughter no less. It is very likely that Isaac and Rebecca would have been delighted with her. Yet, the whole thing was a farce, intended to mislead and confuse. It is what in modern parlance we may call a “deep fake.”

Most people would take one look at Machalat and conclude that Esau was a reformed man. And that is exactly what he intended.

The world can be a confusing place at times. Sometimes evil disguises itself as good. Bad people dress themselves up as decent people. Not everything is as it seems; people can be motivated by twisted intentions. Don’t be fooled by grand gestures designed to make a good impression. Look to the whole person to see if their lifestyle is truly consistent with their claims.

Adapted from Likutei Sichot, vol. 35, Parshat Toldot II.