Our Gemara on Amud Beis discusses the laws concerning a death-bed gift. Since the person is giving away his possessions with the tacit understanding that he is mortally ill, should he recover, his gifts are retracted. 

The Divrei Mahari relates this (Toldos Bereishis 25:30-34) to Esav’s selling of his rights to the firstborn.  

וַיָּ֥זֶד יַעֲקֹ֖ב נָזִ֑יד וַיָּבֹ֥א עֵשָׂ֛ו מִן־הַשָּׂדֶ֖ה וְה֥וּא עָיֵֽף׃ 

Once when Yaakov was cooking a stew, Esav came in from the open, famished. 

וַיֹּ֨אמֶר עֵשָׂ֜ו אֶֽל־יַעֲקֹ֗ב הַלְעִיטֵ֤נִי נָא֙ מִן־הָאָדֹ֤ם הָאָדֹם֙ הַזֶּ֔ה כִּ֥י עָיֵ֖ף אָנֹ֑כִי עַל־כֵּ֥ן קָרָֽא־שְׁמ֖וֹ אֱדֽוֹם׃ 

And Esav said to Yaakov, “Give me some of that red stuff to gulp down, for I am famished”—which is why he was named Edom (Red).

וַיֹּ֖אמֶר יַעֲקֹ֑ב מִכְרָ֥ה כַיּ֛וֹם אֶת־בְּכֹרָֽתְךָ֖ לִֽי׃ 

Yaakov said, “First sell me your birthright.” 

וַיֹּ֣אמֶר עֵשָׂ֔ו הִנֵּ֛ה אָנֹכִ֥י הוֹלֵ֖ךְ לָמ֑וּת וְלָמָּה־זֶּ֥ה לִ֖י בְּכֹרָֽה׃ 

And Esav said, “I am at the point of death, so of what use is my birthright to me?” 

וַיֹּ֣אמֶר יַעֲקֹ֗ב הִשָּׁ֤בְעָה לִּי֙ כַּיּ֔וֹם וַיִּשָּׁבַ֖ע ל֑וֹ וַיִּמְכֹּ֥ר אֶת־בְּכֹרָת֖וֹ לְיַעֲקֹֽב׃ 

But Yaakov said, “Swear to me today.” So he swore to him, and sold his birthright to Jacob.

וְיַעֲקֹ֞ב נָתַ֣ן לְעֵשָׂ֗ו לֶ֚חֶם וּנְזִ֣יד עֲדָשִׁ֔ים וַיֹּ֣אכַל וַיֵּ֔שְׁתְּ וַיָּ֖קׇם וַיֵּלַ֑ךְ וַיִּ֥בֶז עֵשָׂ֖ו אֶת־הַבְּכֹרָֽה

Yaakov then gave Esau bread and lentil stew; he ate and drank, and he rose and went away. Thus did Esav belittled the birthright.

The simple reading of the verse is that Esav’s selling of the birthright, perhaps especially for a bowl of soup, is itself an act of desecration. However, Divrei Mahari says, since Esav could have claimed that his forfeiture was only with the understanding that he was mortally ill, once he recovered he had the option of reneging on the gift. Since he did not, this was a de facto devaluing of the birthright. He gave up too easily.

(Even though he also made an oath, I believe Divrei Mahari would counter that the oath was also implicitly tied into the condition of his death.)

There is a psychological peshat in Esav’s behavior, based on the principles of Confirmation Bias. Confirmation Bias is the psychological term for the investment we have in confirming opinions we already have decided, and selectively filtering out memories and perceptions to reinforce our current belief. 

According to researchers Tavris and Aronson (Tavris, C., & Aronson, E. (2007). “Mistakes were made (but not by me): Why we justify foolish beliefs, bad decisions, and hurtful acts.” Harcourt.) 

“As fallible human beings, all of us share the impulse to justify ourselves and avoid taking responsibility for any actions that may turn out to be harmful, immoral, or stupid.”

A cognitive distortion that is a subset of Confirmation Bias is the Irrational Primacy Effect. That is, the illogical extra credibility we place on something we hear first. (The Rambam, in his introduction to Sefer Hamitzvos, rails against people who foolishly believe in the first opinion they hear, and reject subsequent opinions, despite the new opinion being more logical.)

The Gemara (Yoma 86b) says if a person sins, and then repeats his sin, it becomes as if it is permitted to him. This is because of the fear of facing the truth, so one must rationalize that he is not an evil person. Rav Yisrael Salanter is said to have quipped, and if you then persist and sin for a third time, it becomes a Mitzvah!

In all these instances, the need to continue to feel that one is right, holds the correct decisions and/or morality, filters perceptions and causes bias in judgements which favor the needed belief.

After Esav sold the firstborn, he did not want to allow himself Seller’s Remorse. Instead of feeling regret for his impulsive decision, he told himself “Who needs these dumb firstborn rights, anyway?” 

How many times do we stick to our guns because we are too proud to admit we are wrong, doubling down and doubling the damage?

Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation

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