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Many commentators explain why Itzhak was wrong in his decision to bless Eisav. Then, when Rivka heard it, she asked Yaakov to stage a hoax and "steal" the Brochos. This is completely understandable.

Everybody agrees (see why-doesnt-yaakov-object-to-his-mothers-plan) that the proper way of dealing with a cheater is to cheat, but why to cheat his own father? It seems very plausible that Yaakov could deal with Itzhak reasonably and talk him out of blessing Eisov. Such a way would have numerous benefits - everybody would be happy, he wouldn't have to disrespect his father, he wouldn't need to run away from his brother and hide for two decades putting his parents in misery.

So why didn't Yaakov choose to explain the truth to his father and let his father deal with Eisov's lies instead of staging a hoax that everybody suffered from for decades?

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It seems from many commentaries that Yitzchak was indeed aware of Esav's negative habits, and that even so Yitzchak was trying to encourage Esav to become righteous. By blessing him he would give him the power to overcome his negative habits.

Rabbi Nataf brings a very interesting explanation in the JewishPress.com from the Medrash (Shir Hashirim Zuta 1:13) that Esav had the potential to be the fourth Patriarch!!

Esav had great potential that Yitzchak was trying to encourage.

As an online commentator stated: "According to Midrashim and other sources, Esau possessed great potential. His spiritual and physical powers exceeded even those of his saintly father and brother. Being "a digger of wells," Isaac saw deep into Esau's soul and recognized that it hailed from a loftier place -- and that's why he loved Esau more that Jacob. That's why Isaac tried to steer Esau onto the path of righteousness by giving him the blessing."

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    Sorry, how exactly does your answer address the question? Eisov had potential and therefore... what? – Al Berko Nov 24 '20 at 19:08
  • @AlBerko by blessing him he would give him the power to overcome his negative habits. That's how I understood it. – larry909 Nov 25 '20 at 1:28
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    but the question was why Yacov chose to deceive instead of talking to Dad? – Al Berko Nov 25 '20 at 14:36
  • @AlBerko the whole point is that it's not that Yitzchak doesn't know that esav is a bad guy, he does know, and he still wants to bless him. And yacov knew that. So there's nothing to talk about. What's yacov going to say to Yitzchak? – larry909 Nov 25 '20 at 15:14
  • @larry909 Logically, Isaac did not think Esau was bad. If he did, he wouldn't attempt to bless him, would he? – Turk Hill Dec 8 '20 at 2:03
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It is possible, and this is only speculation, that Jacob wanted the blessing instead. Just as a prince might deceive his father in order to steal the title of a king from the rightful heir. True, Rebecca loved Jacob more than Esau, but Isaac erred in preferring Esau over Jacob, prompting Rebecca to tell Jacob to mislead his father and give him the blessing instead. I think this was wrong. The Tanakh recounts this as unfavorable when Jacob was exiled for many years.

The truth is that there is simply no way of knowing what Jacob was thinking at the time. We can only guess. And anything we guess is subject to speculation. My bet is that Jacob wanted to teach Esau a moral lesson. Esau didn't appreciate the blessings in his life. If Jacob took the blessing meant for Esau, Esau would realize the value of his family and the many blessings that G-d gave him. He would not have sold his birthright for a bowl of lentil soup. He was selfish, only looking after himself, pleasing his own hunger. In contrast, Isaac was selfless, looking after his brother who did not even show up to receive the blessing. Where was Esau anyway?

And to end this with another question, when Isaac realized it was Jacob, why couldn't he retract the blessing? Aren't blessing allowed to be nullified?

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  • 1. "teach Esau a moral lesson", you say. Esau was extremely disturbed hearing that his father left no spare blessings. 2. Is immoral stealing a moral lesson? 3. The question stays - where's Yitzhok in your story? Why course him such a pain? – Al Berko Dec 15 '20 at 21:00
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When Yaakov entered to receive the berachos, it says

https://he.wikisource.org/wiki/%D7%9E%22%D7%92_%D7%91%D7%A8%D7%90%D7%A9%D7%99%D7%AA_%D7%9B%D7%96_%D7%9B%D7%96

וַיִּגַּשׁ וַיִּשַּׁק לוֹ וַיָּרַח אֶת רֵיחַ בְּגָדָיו וַיְבָרֲכֵהוּ וַיֹּאמֶר רְאֵה רֵיחַ בְּנִי כְּרֵיחַ שָׂדֶה אֲשֶׁר בֵּרֲכוֹ יְהוָה.

And he drew close and he kissed him and he smelt the scent of his clothes and he said, "Behold the scent of my son is like the scent of the field that has been blessed by Hashem."

The medrash comments

בשעה שנכנס אבינו יעקב אצל אביו נכנסה עמו גן עדן הדא הוא דא”ל ראה ריח בני כריח השדה

When Yaakov entered to be close to his father the scent of Gan Eden entered with him...

In reference to your question, it would seem that a point that the medrash is making is as follows:

If you directly address an issue in the sphere of activity in which you are operating, then you will always cause a perturbation within that sphere of activity. You can be as right as you like, that is totally irrelevant.

Further: Gan Eden is a pristine image of the way Hashem wants the world to appear. If you cause a perturbation, that image will disappear, much as a reflected image in a pond vanishes when you throw a stone into the pond.

(Note: I think this was Adam's mistake, he disturbed the image (for whatever reason)).

Yaakov only merited that the scent of Gan Eden entered with him because he raised himself up totally above the sphere of activity in which there was hisnagdus between Esav and himself, and did not address it directly.

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  • Thank you, but, again, how does this explain the cheat? Knowing all that Yaakov could talk to his father reasonably IMHO. – Al Berko Dec 15 '20 at 20:56
  • @AlBerko In other words (hope this makes sense to you): If you have an olam ha'dimyon which has certain kochos le'tov in it, you can only access those kochos by entering into the olam ha'dimyon. If you are mevatel the olam ha'dimyon through reason, that will not help you access the potential that lies within it. In kabbalistic terminology this is probably something like the klipah. – The GRAPKE Dec 15 '20 at 21:13
  • IIRC, the struggle wasn't between Yaakov and Esau, but between Yaakov and his father. The question asks why Yaakov couldn't talk to his father about it. – Al Berko Dec 16 '20 at 20:42
  • @AlBerko He couldn't talk to his father because Esav was part of the world in which Yaakov lived. – The GRAPKE Dec 16 '20 at 21:37

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