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I learned from a rabbi that, if you live to see the 4th generation, your great-grandchildren, you automatically get into Olam HaBah. I love this idea. I know that all of Israel gets in - but this differentiates that group somehow. I cannot find the source. Does anyone know it?

Adding this, not sure it's good enough of an answer but would love your feedback:

I found this midrash that might work? this section from Midrash Tehillim 119 almost gives it by the transitive property (If you keep Torah God will 1 - keep your soul and 2 - allow you to see grandchildren.)

What is "take care"? God said, "If you keep the Torah, I will keep your soul" (Talmud, Shabbat 127a). Therefore it is said, "Take care and keep your soul diligently all the days of your life" (Deuteronomy 4:9). What are "all the days of your life"? If you do the Torah all the days of your life, you will merit to see children and grandchildren. Therefore it is said, "And you shall teach them to your children and your grandchildren" (Deuteronomy 4:9). And if you see children and grandchildren, then there will be peace, as it is said, "May you see your children's children! Peace be upon Israel!" (Psalms 128:6).

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    Seems much easier than doing mitzvot and learning Torah. Let's all just have babies at 10 and commit suicide at 50.
    – Double AA
    Aug 20, 2023 at 13:20
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    I cannot comment if anyone says it, however from sanhedrin 69b it seems clear that אחיתופל lived to see his 4th generation, and the mishna sanhedrin 90a says he has no portion in olam haba. It would appear at least that Talmud bavli does not accept this assumption, or at least that one can still lose their portion.
    – אילפא
    Aug 20, 2023 at 14:14
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    There are many statements from our sages that seem absolute but are actually only indicating a direction. If this statement exists, it is obviously one of those.
    – MichoelR
    Aug 20, 2023 at 17:20
  • אַל תִּהְיוּ כַעֲבָדִים הַמְשַׁמְּשִׁין אֶת הָרַב עַל מְנָת לְקַבֵּל פְּרָס, אֶלָּא הֱווּ כַעֲבָדִים הַמְשַׁמְּשִׁין אֶת הָרַב שֶׁלֹּא עַל מְנָת לְקַבֵּל פְּרָס
    – Rabbi Kaii
    Dec 24, 2023 at 20:22
  • Interesting I love this idea Jan 18 at 0:08

2 Answers 2

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The Leket Yosher says it's customary to appoint the great-grandfather sandek at a bris because there's a saying that one who is sandek for his great-grandson will not see gehinnom:

מי שיש לו בן למול ואינו רוצה להיות בעל ברית, ורוצה לכבד אחרים משום הבאת שלום ומשום דיש בו כבוד הבריות, חייב ליתן לאביו קודם אביו זקנו להיות בעל ברית. אבל אם הוא ברצון אביו יוכל לתן לזקנו, והמנהג ליתן לזקנו משום שהעולם אומרים מי שהוא בעל ברית לבן נינו אינו רואה פני גהינם

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  • See here for a more speculative source.
    – shmosel
    Jan 18 at 0:00
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I have never heard this before, but it is reminiscent of an idea in the Torah rules of reincarnation.

Based on the pasukim in Shemot 20:5-6

לֹא־תִשְׁתַּחֲוֶה לָהֶם וְלֹא תׇעׇבְדֵם כִּי אָנֹכִי ה אֱלֹקֶיךָ אֵל קַנָּא פֹּקֵד עֲוֺן אָבֹת עַל־בָּנִים עַל־שִׁלֵּשִׁים וְעַל־רִבֵּעִים לְשֹׂנְאָי׃

You shall not bow down to them, nor serve them: for I, Hashem your God am a jealous God, punishing the iniquity of the fathers upon the children unto the third and fourth generation of those that hate Me;

וְעֹשֶׂה חֶסֶד לַאֲלָפִים לְאֹהֲבַי וּלְשֹׁמְרֵי מִצְוֺתָי׃        

but showing mercy to thousands of generations of those that love Me, and keep My commandments.

The pshat of this is talking about familial generations, but the secret here is talking about one's reincarnations. The Arizal teaches us, in conjunction with Iyov 33:29, Amos 2:6 and Sefer HaTikkunim 69 that this is coming to teach us that if a person is reincinarnated a 4th time, they are guaranteed Olam Haba. See Shaar HaGilgulim 4:6.

This is esoteric Torah, but the very short and basic explanation is that if a person comes back 3 times and doesn't accomplish any rectification in any of those 3, then he will not be reincarnated again, but will be cut off, ch'v.

However, if in those 3 he completes even one rectification, not only will he now be zoche to be reincarnated up to 1000 times, but Hashem guarantees that He will achieve complete rectification.

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  • I took the liberty of adding in a link to the Shaar HaGilgulim you cited, please feel free to roll back. Aug 20, 2023 at 20:12
  • However the pshat there appears to provide this guarantee from the fifth gilgul rather than the fourth. Aug 20, 2023 at 20:12
  • thanks @יהושעק Can you explain how you hear fifth? ואם לא נתקנה אז, חוזרת בגלגול שלישי. ומשם ואילך, אין לה עוד תקנה בגלגול, ואז נאמר בה, ונכרתה הנפש ההיא מעמיה לגמרי. אמנם אין זה, רק כאשר לא נתקנה כלל שום תקון בשום פעם מאלו, אבל אם באיזה פעם מאלו השלשה, התחילה לתקן קצת, אינה נכרתת
    – Rabbi Kaii
    Aug 20, 2023 at 20:16
  • Essentially it depends if you want to source the number of gilgulim in Iyov (2-3), Amos (3 but not 4) or Shemot (3 and even 4). my set of Kitvei Ari are in temporary storage so I'll quote directly from Chabad's translation: 'Those who hate G‑d are the evil people, to whom the four-generation limit on reincarnations applies. Those who love G‑d are the righteous people, to whom "a thousand generations" of reincarnations applies.' Aug 20, 2023 at 20:32

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