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At the end of Parshat Toldot, Eisav marries the daughter of Yishmael, as he "perceives" that the daughters of Heth have upset his parents.

Whilst obviously Eisav had many flaws, this appears to be a reasonable marriage, or at least the lineage is. So why does Rashi criticise him for this too and cause her "yet another unsuitable wife"?

The actual words are that he "added wickedness upon wickedness" because he did not divorce his other wives.

Would divorcing them have been the right thing? Eliphaz was being educated by Yitzchak (and thus did not kill Jacob when instructed to). So perhaps keeping them near his father was the right thing to do? And why would it be "adding wickedness"?

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  • You seem to be asking two completely separate questions here -- whether and how his new wife was wicked, and whether he should've divorced his existing wives. Am I reading that right? Did you mean to combine them into one question post?
    – msh210 ♦
    Nov 9, 2015 at 18:18
  • @msh210 There are 2 questions in a sense here but I feel it should be one post they are 2 sides of the same Rashi on the same Pasuk.
    – CashCow
    Nov 10, 2015 at 10:31
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On a peshat level, once Esav realized his father disapproved of his Canaanite wives (Genesis 28: 8) he righteously married wives from his extended family as per his father's general wish (Genesis 28: 9).

בראשית פרק כח (ח) וַיַּ֣רְא עֵשָׂ֔ו כִּ֥י רָע֖וֹת בְּנ֣וֹת כְּנָ֑עַן בְּעֵינֵ֖י יִצְחָ֥ק אָבִֽיו: (ט) וַיֵּ֥לֶךְ עֵשָׂ֖ו אֶל־יִשְׁמָעֵ֑אל וַיִּקַּ֡ח אֶֽת־מָחֲלַ֣ת׀ בַּת־יִשְׁמָעֵ֨אל בֶּן־אַבְרָהָ֜ם אֲח֧וֹת נְבָי֛וֹת עַל־נָשָׁ֖יו ל֥וֹ לְאִשָּֽׁה

However, there exists a Midrashic tendency to vilify Esav, consistent with the general Midrashic tendency of ascribing every possible flaw to bad people, noted by R. Abraham the son of Maimonides in his Torah commentary (Exodus 14:11):

וזו השערה על ההצעה האומרת כל שאתה יכול לתלות ברשעים תלה

In this vein, the new wives are instead portrayed as being similarly unsuitable, and he is censured for not divorcing the first.

Perhaps the textual justification for this derasha is the apparently superfluous mention of "al nashav" in addition to his wives in verse 9. This would be Midrashically interpreted as emphasizing similarity between the wives, and emphasizing that in spite of recognizing that his first wives displeased his father, he did not divorce them.

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It seems like he was following the 'letter of the law'. Yitzchok mentioned his dismay over the local girls, of Canaan. He obviously didn't see Yishmael as the solution if he sent Yaakov far away. Esav, hearing that the issue is Canaan found himself a loop hole.

This follows the pattern of ציד בפיו, which Rashi explains means that he would try to appear devout while remaining far from it.

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  • Also consider that Avraham sent Eliezer to Padan Aram and did not consider the daughters of Yishmael as a possibility. Also as Rav Hirsch points out, Yitzchak sent Yaakov to Padan Aram as well. We see that the daughters of Yishmael were not valid to take for a wife.
    – sabbahillel
    Nov 10, 2015 at 17:41
  • That point about Yitzchok is the thrust of my answer but about Avraham it might not be good enough since we find after all that Eliezer said (24:49) 'If not, tell me and I'll go right or left.' And Rashi explains that that was a reference to Yishmael and Lot.
    – HaLeiVi
    Nov 12, 2015 at 5:16
  • Rav Hirsch points out that it was a ruse to convince the family to approve the match. Avraham did not say that because the two possibilities were the daughters of Yishmael and Eliezer, neither of whom was actually a valid match.
    – sabbahillel
    Nov 12, 2015 at 14:55

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