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We know that Yishmael early on acted in an improper manner (see for example Bereishis Rabbah 53:11) and was resultantly banished from Avraham's household - Bereishis 21:9-10

However, we learn later on (Bereishis 25:9) that following Avraham's death, Yishmael returned to bury his father along with Yitzchak. Rashi there qualifies this to mean:

יצחק וישמעאל. מִכָּאן שֶׁעָשָׂה יִשְׁמָעֵאל תְּשׁוּבָה וְהוֹלִיךְ אֶת יִצְחָק לְפָנָיו, וְהִיא שֵׂיבָה טוֹבָה שֶׁנֶּאֱמַר בְּאַבְרָהָם (בראשית רבה):

ISAAC AND ISHMAEL — From this we gather that Ishmael repented of his evil ways (cf. Bava Basra 16b) and yielded the precedence to Isaac. This is what is meant by the “good old age” mentioned in connection with Abraham (Bereishis Rabbah 38:12).

With this in mind, how then do we understand the pretty tough line we see in a couple of places against Yishmael:

  1. Sanhedrin 104a - Avraham cannot save Yishmael (from his heavenly judgement)
  2. Pesachim 119b - In the future Hashem will make a feast for the righteous. The cup of blessing will be given to Avraham (so that he can lead bensching) but he will say, "I will not recite the blessing because Yishmael issued from me."

I appreciate Yishmael gave rise to a nation that would be an enemy of the Jews, but on an individual level why should he continue to warrant punishment if he was chozer b'teshuva?

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    I thought it was because by the time he did teshuvah, his kids already learned his bad behavior. It's not Yishmael the human who is being spoken of, but Yishmael the nation(s). I could look up sources and things, but it would be too much fuel for a sonei Yisrael who has access to Google. (In either case, a given individual isn't the same person as a national stereotype.) – Micha Berger Aug 7 '20 at 19:38
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There seems to be some question and differing opinions about whether he did complete Teshuva or not . Most opinions hold that he did complete Teshuva.

However,The Tosfos Yeshanim Yoma 38B, asks a similar question to the one being asked here; How can we use the name Yishmael if based on the Gemora Sanhedrin mentioned in this question he was a Rasha? He answers that since Hashem was the one to choose and make the name Yishmael it is used despite the way he turned out. He seems to be reaching the conclusion that according to that Gemara, Yismoal indeed never did complete Teshuva.

Rashi on Chumash brings down the Medrash of Yismael doing Teshuva, yet Rashi also (Megilah 17A) refers to him as a Rasha.

According to those that he remained a Rasha he must have done Teshuva for some things as the Midrash says. But not all.So in one sense yes he did Teshuva. But in other areas he remained a Rasha.

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  • Are there opinions which say he did do a complete teshuvah? If so, how do they resolve the contradictory Gemaras brought by OP? – DonielF Aug 7 '20 at 18:53
  • Most opinions are that he did full Teshuva. I don't know how they answer the Gemoras but my boich sevora is that (1)The Gemorah in Pesochim is saying that Avraham did not want to bentsch because he had a son who for a TIME was a baal aveira (2)The Gemora in Sanhedrin is saying that in THEORY had Yismoel not done Teshuva Avraham would not have been able to save him from punishment. – Schmerel Aug 7 '20 at 19:45
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Rabbi Akiva Eiger (Gilion hashas baba basra 16b) brings the Toras Chaim who asks on the gemara in Sanhedrin 104a that why did Yishmael need saving if he did teshuva. However the Reishonim in Yuma 38b imply that the gemara in Sanhedrin held Yishmael didn't do Teshuva. Therefore it's a machlokes whether Yishmael did teshuva or not. I've seen Rav Yehonasan Eibshitz say that the gemara in Pesachim 119b holds Yishmael didn't do Teshuva. On the haga they comment it's not neccessary to say that, but rather it's reffering to the nation of Yishmael. Since that nation came out of him, Avraham wouldn't be allowed to bless.

Regarding the drasha in Baba Basra that mentions Yitschak before Yishmael implying that Yishmael did teshuva, I've seen in the chumash Hagra that he explains the pasuk according to the one that holds Yishmael didn't do Teshuva. He explains the pasuk mentions Yitschak first because he was the ben hagvira and Yishmael was the son of the maid. However I think you can explain differently based off the Gur Aryeh. The Gur Aryeh asks on Rashi what's the proof Yishmael did Teshuva, maybe he allowed Yitschak to go first because he was giving honor to the ben Hagvira (see there what he answers). I think that's what the Midrash Rabba is saying on this pasuk.The medrash says from here the son of the maid gave honor to the ben hagvira, implying that Yishmael didn't do teshuva.

There is some more gemaras that might need to be answered up, however I won't address them now, because they weren't mentioned in the question. Also the Bear Bisadeh tries to reconcile the gemara in Sanhedrin with Yishmael doing teshuva but I don't remember where he is. However probably he didn't see the reishonim in Yuma.

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  • +1 - Yasher Kochacho! – Dov Oct 2 '20 at 15:33

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