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Rav Yosef Yehuda Leib Bloch in the sefer Shiurei Da'as (page 178) is quoted as having said that there are many places in the words of Chazal that Teshuva is against the sechel.

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I'm looking for sources in Chazal that say such a thing. I'd also be happy with sources from "seforim hakedoshim" as Rav Bloch says, but I am mainly looking for sources in Chazal.

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The Midrash says:

שאלו לחכמה החוטא מהו עונשו, אמרה להם וחטאים תרדף רעה (משלי יג: כא). שאלו לנבואה החוטא מהו עונשו, אמרה להם הנפש החוטאת היא תמות (יחזקאל יח: ד). שאלו לתורה חוטא מה עונשו, אמרה להם יביא אשם ויתכפר לו. שאלו להקב"ה החוטא מהו עונשו, א' להם יעשה תשובה ויתכפר לו, הדא היא דכת' טוב וישר י"י וגו' (תהלים כה: ח)

Translation (Pesikta de-Rab Kahana, trans. William G. Braude, Piska 24:7):

When Wisdom is asked, “The sinner- what is to be his punishment?” Wisdom answers: Evil which pursueth sinners. When Prophecy is asked, “The sinner- what is to be his punishment?” Prophecy replies: The soul that sinneth, it shall die. When Torah is asked, “The sinner- what is to be his punishment?” Torah replies: Let him bring a guilt offering in expiation and his sin shall be forgiven him. When the Holy One is asked, “The sinner- what is to be his punishment?” the Holy One replies: In penitence let him mend his ways, and his sin shall be forgiven him. Hence it is written, [At one and the same time] kind and strict judgement is the Lord.

This implies that teshuvah does not follow the normal dictates of chochmah, nevuah, or even Torah. Only Hakadosh Baruch Hu allows the sinner to perform teshuvah. The Maharal also explains Chazal this way.

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  • This Midrash also appears in Yerushalmi Makkos 2:6, Yalkut Shimoni Tehillim § 702, and Otzar HaMidrashim p. 494 – robev Sep 23 '20 at 14:56
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Not from Chazal, but this probably counts as sefarim hakedoshim.

Mesillat Yesharim 4:

לפי שורת הדין ממש: היה ראוי שהחוטא יענש מיד תיכף לחטאו בלי המתנה כלל. וגם שהעונש עצמו יהיה בחרון אף, כראוי למי שממרה פי הבורא יתברך שמו. ושלא יהיה תיקון לחטא כלל. כי הנה באמת, איך יתקן האדם את אשר עיות והחטא כבר נעשה? הרי שרצח האדם את חברו, הרי שנאף, איך יוכל לתקן הדבר הזה? היוכל להסיר המעשה העשוי מן המציאות. אמנם, מדת הרחמים היא הנותנת הפך השלשה דברים שזכרנו: דהינו, שיתן זמן לחוטא ולא יכחד מן הארץ מיד כשחטא. ושהעונש עצמו לא יהיה עד לכלה. ושהתשובה תנתן לחוטאים בחסד גמור, שתחשב עקירת הרצון כעקירת המעשה.‏

[A]ccording to strict justice it would be proper that:

  • the sinner be punished immediately for his sin without any delay whatsoever.

  • that the punishment itself be wrathful as befits one who rebels against the word of the Creator, blessed be His Name.

  • that there be no possible repair whatsoever for the sin.

For in truth, how can a man rectify what he has made crooked after committing the sin? If one murdered his fellow or committed adultery? How can he possibly rectify this? Can he undo a deed already done from existence?

But the attribute of mercy reverses the three aforementioned matters.

  • it grants that the sinner be given time and not be eradicated from the earth immediately upon sinning.

  • that the punishment itself not utterly destroy him.

  • that the opportunity of repentance be granted to sinners as a complete kindness, so that the uprooting of the will be counted as the uprooting of the deed.

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It could be written in other places, but in Kochavei Ohr 3:12 Rav Yitzchak Blazer says definitively:

אוּלָם כְּכָל אֲשֶׁר יַרְבֶּה הָאָדָם לְהַכִּיר וּלְהַבְחִין אֶת מִשְׁקַל כֹּבֶד עָו‍ֹן. וּלְהָבִין וּלְהַשְׂכִּיל אֶת גֹּדֶל הָרָעָה וְהָאַשְׁמָה הָרַבָּה שֶׁל חֵטְא וְעָו‍ֹן. לְהַמְרוֹת אֶת רְצוֹן ה' יִתְבָּרַךְ שְׁמוֹ מֶלֶךְ מַלְכֵי הַמְּלָכִים הַקָּדוֹשׁ־בָּרוּךְ־הוּא. כֵּן יִהְיֶה אֵלָיו יְסוֹד הַתְּשׁוּבָה בְּיוֹתֵר נֶגֶד דַּרְכֵי הַשֵּׂכֶל:

But no matter how much a person may recognize and discern the weight of iniquity, to understand and grasp the great sense of evil and the immense guilt of sin and iniquity, in order to convert the will of G-d, may His name be blessed, the foundation of repentance will be to him, seemingly against the ways of reason.

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  • Comments are not for extended discussion; this conversation has been moved to chat. – msh210 Sep 23 '20 at 20:58
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Rav Elchonon Wasserman (דוגמאות לביאורי אגדות על דרך הפשט סימן ג - הודפס בסוף קובץ הערות) quotes the mesilas yesharim ch. 4 as the source for this idea (as @Joel K wrote).

I believe that this is also the intent of the opening words of the Shaarei Teshuva (Rabbeinu Yona of Girundi - perhaps the most authoratative work on the subject of Teshuva):

"מן הטובות אשר היטיב השם יתברך עם ברואיו, כי הכין להם הדרך לעלות מתוך פחת מעשיהם ולנוס מפח פשעיהם, וכולהו." It is from the good things that Hashem may He be blessed has done with his creations, that he has prepared for them the way to rise up from the lowliness of their deeds and to escape from the lowliness of their sins, etc."

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