Gedolah Teshuvah

Parshah Insights | September 03, 2026

וְשַׁבְתָּ עַד־ה' אֱלֹקֶיךָ וְשָׁמַעְתָּ בְקקֹלוֹ כְּכֹל אֲשֶׁר־אָנֹכִי מְצַוּךְ הַיּוֹם אַתָּה וּבָנֶיךָ בְּכָל־לְבָבְךָ וּבְכָל־נַפְשֶׁךָ: (לב)

You will return to Hashem, your G-d, and obey Him exactly as I am commanding you today, you and your sons, wholeheartedly and with your whole being.

Waking Call

The Beis Aharon teaches that we specifically read parshas Nitzavim on the Shabbos before Rosh Hashanah because it discusses the mitzvah of teshuvah. He cites the well-known idea that the Shabbos before a yom tov is a time to prepare for the upcoming holiday spiritually. Hence, פְּשִׁיטָא שַׁבָּת שֶׁקֹּדֶם ר"ה צָרִיךְ לְהִתְעוֹרֵר עַצְמוֹ בִּתְשׁוּבָה לִפְנֵי הקב"ה - It is clear that on the Shabbos preceding Rosh Hashanah, one is to awaken themselves in repentance before Hashem.

(בֵּית אַהֲרן נִצְבִים)

But the Torah not only commands us to do teshuvah. It teaches us about teshuvah's transformative power, and its role as a means of remaining close to Hashem.

The Function of Teshuvah

In this week's parshah, Moshe Rabbeinu draws a vivid picture of what will transpire in the nation's future. He warns individuals, families, and tribes to remain devoted to Hashem and not turn to worship the gods of other nations. He warns that straying will lead to bitterness and curse. He describes the consequences of forsaking our covenant with Hashem, including being cast out of the land and scattered among other nations.

When teaching about the negative outcomes of sin, it might seem like the focus should be solely on avoiding sin altogether. However, Moshe Rabbeinu takes a different approach. Instead of elaborating on the importance of steering clear of sin, he goes on to offer hope and the promise of restoration if we sincerely return to Hashem and follow His commandments. He speaks of Hashem's mercy and the blessings that await us when we wholeheartedly return to follow His commandments. In doing so, Moshe Rabbeinu gives us deeper insight into the meaning of teshuvah, its function and role in our lives.

The Torah's View of Sin

The Chovos Halevavos, in his introduction to the chapter Shaarei Teshuvah, explains that teshuvah is not merely a way to escape punishment, but a means to rectify our natural shortcomings.

He emphasizes that both reason and scripture support the idea that human beings inevitably fall short in fulfilling their service to the Creator. Recognizing this reality, the Creator, out of Divine grace, has given us the capability to rectify our mistakes and return the loss of service through repentance.

The Chovos Halevavos highlights that it was a chessed from Hashem to encourage and enable us to repent, and He promised its effectiveness through His prophets. Moreover, Hashem desires our quick return, even if we rebelled against His word and broke His covenant for a long time.

(חוֹבוֹת הַלְּבָבוֹת הַקְדָּמָה לְשַׁעַר הַתְּשׁוּבָה)

Rabbeinu Yonah derives from our parshah that Hashem's grace extends even further. The Torah (לו) relates what will happen after we repent wholeheartedly, וּמָל ה' אֱלֹקֶיךָ אֶת לְבָבְךָ וְאֶת לְבַב זַרְעֶךָ לְאַהֲבָה אֶת ה' אֱלֹקֶיךָ בְּכָל לְבָבְךָ וְכָל נַפְשְׁךָ לְמַעַן חַיֶיךָ - And Hashem, your G-d, will circumcise your heart and the heart of your offspring, [so that you may] love Hashem your G-d with all your heart and with all your soul, for the sake of your life.

This implies, says Rabbeinu Yonah, that not only does Hashem grant us the ability to repent, but He also assists those who return to Him to achieve beyond their natural capacity. He renews a pure spirit within them, enabling them to reach great heights in their love for Him.

(שַׁעֲרֵי תִּשׁוּבָה הַשַּׁעַר הָרִאשׁוֹן)

As pointed out by both the Chovos Halevavos and Rabbeinu Yonah, scripture is replete with references to the transformative power of teshuvah. Chazal, too, continuously cite instances where genuine repentance has uplifted even the most deeply entrenched sinners.

Menashe, the Penitent King

One such example is Menashe, the king of Yehudah. He is depicted in Nevi'im in the worst terms. In Divrei Hayamim (ב, לג ב-ז) Menashe is described as performing "despicable acts" in the eyes of Hashem, emulating the abominations of the nations previously expelled from the Land of Yisrael.

And then comes a summary of all his horrible misdeeds: Not only did he rebuild the idolatrous sites that his father, Chizkiyahu, had destroyed, but he also erected altars to the Ba'alim, set up asherah poles, worshipped the entire celestial host, and performed child sacrifices in the valley of Ben-Hinnom. Additionally, he practised sorcery and placed an idol in the Beis Hamikdash. Menashe's actions led Yehudah and the inhabitants of Yerushalayim to commit even greater evils than the nations vanquished before them by Hashem.

For twenty-two years Hashem continuously sent prophets to rebuke Menashe and his people, but to no avail. No one paid heed.

The Dramatic Transformation

All this went on until the fateful day arrived and Hashem brought the Assyrian army upon them. Menashe was taken captive. They bound him with hooks and copper chains, and they led him to Bavel. In his torment, the Navi tells us, Menashe entreated Hashem, and he humbled himself greatly before Him. Hashem accepted his supplication and returned him to Yerushalayim to his kingdom.

Though the reason for Menashe's sudden change of heart is not mentioned by the Navi, and the precise nature of his "torment" is quite unclear, Chazal clarify the missing details:

The Assyrians, known for their cruelty, placed Menashe in a copper cauldron (hinted in scripture by the word נְחְשְׁתַּיִם, lit. "coppers"), and began heating it from below. When he realized he was in real trouble, he appealed to every idolatrous deity, but this, of course, did not help him at all.

And then he reminisced how his father, Chizkiyahu Hamelech, made him read the following verses: בַּצַר לְךָ וּמְצָאוּךְ כֹּל הַדְּבָרִים הָאֵלֶּה בְּאַחֲרִית הַיָּמִים וְשַׁבְתָּ עַד־ה' אֱלֹקֶיךָ וְשָׁמַעְתָּ בְּקוֹלוֹ: כִּי קֵל רַחוּם ה' אֱלֹקֶיךָ לֹא יַרְפְּךָ וְלֹא יַשְׁחִיתֶךָ וְלֹא יִשְׁכַּח אֶת־בְּרִית אֲבֹתֶיךָ אֲשֶׁר נִשְׁבַּע לָהֶם - When you are in straits, and all these things will find you in the future, then you will return to Hashem, your G-d, and listen to His voice. For Hashem, your G-d, is a merciful G-d. He will not let you slacken; He will not destroy you, nor will He forget the covenant of your forefathers which He had sworn to them (דְּבָרִים ד ל-לא).

Menashe decided to reach out to Hashem. He thought to himself: "If He hears me, well and good; if not, then (I will know that) all gods are the same."

Tunnelling the Heavens

The angels, upon seeing Menashe turn to Hashem, closed off the windows of heaven so that his prayer wouldn't ascend. They questioned: "Would You, Master of the Universe, accept the repentance of a man who worshipped other powers and placed an idol in the Temple Hall?" Hashem responded: "If I didn't accept the penance of this man, I would be shutting the door on all repentant sinners." Hashem then "dug a hole," so to speak, beneath His Kisei Hakavod, and accepted Menashe's supplication through it.

Our sages go on to relate the wonderous circumstances of Menashe's rescue and restoration to kingdom in Yerushalayim. The pasuk says, וַיִשִׁיבֵהוּ יְרוּשָׁלַיִם לְמַלְכוּתוֹ - And He (Hashem) returned him to Yerushalayim to his kingdom. However, Chazal interpret the word "וַיִשִׁיבֵהוּ" as if it would have read "וַיַּשִׁיבֵהוּ" - and He blew him... hinting to the fact that when Menashe repented, Hashem sent a mighty gust of wind which blew Menashe right out of the cauldron in Bavel, straight to Yerushalayim!

(יְרוּשַׁלְמִי סַנְהֶדְרִין פ"י ה"ב, דְבָרִים רַבָּה ב כ)

Anyone, Anytime

With this miracle, Hashem essentially "opened the door" for future sinners, showing them the power of teshuvah. This event serves as a powerful demonstration of Divine mercy and forgiveness, offering hope to all who may have felt unworthy or hopeless.

Many lessons can be extracted from this story, but Reb Yosef Albo, in his Sefer Ha'ikrim, highlights two profound concepts taught by it: Firstly, when it comes to teshuvah, a person's history makes no difference. Even if they were once considered the personification of all that is evil, sincere repentance is always welcomed and accepted. Everyone is eligible.

Secondly, Reb Yosef draws attention to the nature of King Menashe's teshuvah. The verse indicates that he turned to Hashem "in his torment," and according to Chazal, this act of repentance was the last thing on his mind. He only sought help from Hashem when all else had failed. This raises the question: Would we accept someone who has turned their back on us their entire life, only seeking our help when things go bad? Most likely, we would not be inclined to do so. However, Hashem's response is different. The Torah repeatedly teaches that when we suffer the consequences of our sins and then genuinely turn to Hashem, even if it is only out of suffering, He will not forsake us; instead, He will accept us with compassion and forgiveness.

(סֵפֶר הָעִקְרִים מַאֲמָר ד טז)

The Tragic Figure of Acher

The same idea is evident in the story of Acher. Acher was originally a great Torah scholar; his name was Elisha Ben Avuyah. His knowledge of Torah was immense - he was the teacher of the great Tanna Rabbi Meir. But he had strayed off the path and he turned against the Torah and opposed it. The once-revered sage became a notorious persecutor of Torah students, actively discouraging Torah study, and even killing excelling students (עיי' יְרוּשַׁלְמִי חֲגִיגָה פ"ב ה"א).

His abandonment of the Torah resulted in his coming to be known as אַחֵר - "the other one," or "the changed one". Rabbi Meir, his disciple, treated him with respect and sought out his company, even after he left the fold.

The Yerushalmi relates that Rabbi Meir was once delivering a Torah discourse in the beis midrash of Teveriah on a Shabbos, when he was interrupted by the arrival of his teacher, Elisha, who was riding on a horse. Rabbi Meir paused his discourse and went outside to greet his teacher. Elisha asked about the topic of the sermon, and Rabbi Meir repeated it to him. It centred on the idea that "the end of a matter is better than the beginning."

The teaching emphasised that even those who had not initially succeeded or had made mistakes in their youth still had the potential to regain what they'd lost, rectify their actions, and relearn what they had missed. Rabbi Meir supported his points with interpretations of various verses, but Elisha offered alternative explanations for each of them.

Elisha's interpretations all claimed that "the good end of a matter solely depends on its beginnings," reflecting his belief that the foundation of any endeavour significantly influences its outcome. He thereby attributed his present situation to the negative impact of a mistake his father made during his formative years.

As their conversation continued, Rabbi Meir discussed the value of Torah study. In scripture, the Torah is compared to gold and glass. Rabbi Meir interpreted the comparison to glass as a lesson that, like broken glass, Torah that has been forgotten can be restored.

At this juncture, Elisha turned to Rabbi Meir (who had been following him all the time) and said: "Enough, Meir, up to here is the techum Shabbos." He explained that he calculated this by counting his horse's footsteps. Rabbi Meir was astounded and asked, "All that wisdom is in you, and you still do not repent?"

Elisha responded that he was unable to repent because of an incident in which he had ridden his horse near the Kodesh Hakadoshim on Yom Kippur, which was also on a Shabbos. He claimed to have heard a voice emanating from the Holiest of Holies, stating, "Return, wayward children, except for Elisha ben Avuyah, who understood My power and defied Me." Elisha took this as a sign that he was destined to remain a sinner for the rest of his life.

Up to the Last Moment

Later on, Elisha fell ill. Word reached Rabbi Meir that his teacher was unwell, so he went to visit him and found him in a weakened state. Rabbi Meir asked Elisha if he had repented, to which Elisha responded by questioning whether repentance at the moment of death would at all be accepted. Rabbi Meir reminded Elisha that one can repent until their last breath, quoting the verse תָּשֵׁב אֱנוֹשׁ עַד דַּכָּא - Man shall repent up to extinction (תְּהִלִים צ ג). Elisha then cried out, and passed away. Rabbi Meir internally felt relieved, saying: "It seems that my teacher had passed away in a state of repentance."

(יְרוּשַׁלְמִי שָׁם)

This story beautifully illustrates the two points discussed above: first, that no one is deprived of the privilege of teshuvah, even someone like Acher, who had clearly been announced as "unwanted;" and second, the fact that teshuvah out of misery is accepted all the same, the idea that genuine repentance is always valued, regardless of the circumstances that led to it. But it gives rise to another point to ponder. If the heavenly voice did not mean that Elisha was unable to repent, what did it mean?

The Apter Rav provides a profound explanation. He says that in reality, there was no difference between Acher and everyone else. If he had only repented, he would have been accepted like every other Yid. The only difference was in the awakening to teshuvah. And here, the Apter Rav explains another concept.

Silent Announcements

The Zohar Hakadosh (פְּרָשַׁת נָשׂא) teaches that every day, an announcement calls out: "How long, ye thoughtless, will ye love thoughtlessness? Return, wayward children, and I will heal your backslidings!" thereby urging humans to reflect on their actions and return to a path of righteousness. The Apter Rav illuminates this concept, explaining that the "announcement" referred to in the Zohar signifies the feelings of remorse and awakening that Hashem instils in the hearts of human beings. This is a manifestation of Divine mercy, as Hashem desires no one to be left abandoned or rejected. Hashem Himself, out of boundless compassion, opens the gates of teshuvah before us and personally calls upon each individual to return to Him.

However, the situation differs for individuals like Acher, and others, like, הָאוֹמֵר אֶחֱטָא וְאָשׁוּב - one who sins on account that he will repent (יומא פה ע"ב). These individuals, due to the grave nature of their sins, are not immediately awakened by Hashem's mercy. Instead, they are required to take responsibility for their actions and initiate their own process of repentance. Nevertheless, this does not mean that their teshuvah, or repentance, will be rejected. On the contrary, Hashem is, "waiting, longing, and hoping" for the day they will awaken to teshuvah, and then, "it is certain that their repentance will be accepted, joyfully."

The Apter Rav concludes with the profound principle taught by our sages: אֵין לְךָ דָּבָר הָעוֹמֵד בִּפְנֵי הַתְּשׁוּבָה - There is nothing that can stand in the way of teshuvah (יְרוּשַׁלְמִי פּאָה פ"א ה"א). This means that repentance always reaches its target, regardless of the circumstances. When the Bas Kol said חוּץ מֵאַחֵר - all but Acher, it meant that the invitation to repent was not meant for his ears, as he was to awaken on his own. Even though he was seemingly singled out, the underlying message was that Hashem longs for everyone to return to Him. The "exclusion" served as a wake-up call, urging him to take personal responsibility for his actions, and that in truth, Hashem was sitting and waiting for his teshuvah. This teaching reminds us that the opportunity for repentance is always open, and no one is beyond the reach of teshuvah or beyond Hashem's desire for our return.

(אוֹהֵב יִשְׂרָאֵל דְּבָרִים לִימֵי הָרָצוֹן וְהַתְּשׁוּבָה)

Let us all awaken to the call of the shofar and recognize the great opportunities given to us. Let us enter the doors of teshuvah which Hashem, in His great mercy, has opened wide for us, regardless of our actions. May we indeed merit to return to our Father wholeheartedly, and may we be blessed with all the brachos promised in our parshah - וְשָׁב ה' אֱלֹקֶיךָ אֶת שְׁבוּתְךָ וְרַחֲמֶךָ וְשָׁב וְקִבֶּצְךָ מִכָּל הָעַמִּים... בִּמְהֵרָה בְּיָמֵינוּ אָמֵן

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