Talmud Tips

For the week ending 17 July 2021 / 8 Av 5781

Devarim: Yoma 86 - Succah 5

by Rabbi Moshe Newman
Library Library Library

How Great Is Teshuva?

Rabbi Levi said, “How great is teshuva! For it reaches unto (Hashem’s) Throne of Glory…”
Rav Yonasan said, “How great is teshuva! For it brings the redemption closer..”
Reish Lakish said, “How great is teshuva! It turns his intentional sins into unintentional sins...” Gemara: Did not Reish Lakish say, “How great is teshuva! For it turns his sins into merits…”? The first statement of Reish Lakish refers to teshuva motivated by fear of Hashem; the second statement refers to teshuva motivated by the love of Hashem.”

Rabbi Meir said, “How great is teshuva! The entire world is forgiven because of one person who has repented…”

These teachings about the greatness of teshuva are taught on our daf by these great Torah sages. As Rabbeinu Yonah of Gerona writes in explaining the great essence and importance of teshuva: “One of the great kindnesses that Hashem bestowed upon His creations is that He prepared a way for them to ascend from the baseness of their deeds, and to flee from the pitfalls of their inequities, to save their souls from destruction and to turn His wrath away from them. He taught them and exhorted them to return to Him if they sinned against Him, because of His abundance of kindness and righteousness, for He is aware of their desires, as it says, ‘Hashem is good and righteous and therefore He guides sinners in the way (of repentance).’” (Sha’arei Teshuva 1:1)

Teshuva is vital for our existence, an indispensible factor in the final redemption, and it is one of the greatest kindnesses that Hashem has bestowed upon mankind. Many important works have been written throughout history to guide us in the way of teshuva, perhaps most notable of which are The Gates of Teshuva by Rabbeinu Yonah and The Laws of Teshuva by Rabbi Moshe ben Maimon (the Rambam). They both list three essential components necessary for teshuva: regret, confession and abandonment of sin. (In Hebrew, these requirements are called charata, vidui and azivat ha’chet.)

In this Talmud Tip, I would like to briefly address the topic of regret — in particular the practical aspect of “regret” when the sinner did not realize at the time that what he did was wrong. This is especially relevant to a person who grew up in a secular environment and only later on began to observe the Torah and its mitzvahs and return to the way of Hashem. This person is widely referred to as a ba’al teshuva — literally“a master of teshuva”, a person who has decided to embrace Torah Judaism, but was not aware of the sin (or the seriousness of the sin) at the time he transgressed beforehand. How can this person truly regret his sins, since he clearly did not know he was doing anything wrong at the time of the sin? How can there be regret without a sense of guilt?

My revered teacher, Rabbi Moshe Shapiro, zatzal, taught me one answer to this question (although other answers can be found in the teachings of the classical Torah commentaries, and are compiled in “After the Return” from Feldheim Publishers.)

Rabbi Shapiro taught me that the mere fact that a person wants to change his ways and return to observe the pleasant ways of the Torah shows that he regrets the sins of his previous way of life. His desire to live in a different way now is a clear indication that he regrets at least certain parts of his past. A person who has abandoned his secular lifestyle, and has accepted the Torah and mitzvahs, has shown a “de facto” regret for his past transgressions. The very act of return to Judaism is a fulfillment of the requirement of “regret”.

Rabbi Shapiro also explained that despite a person’s innocence with regard to transgression, he should nevertheless regret his lost opportunities to fulfill the precepts of the Torah. A person who had a lottery ticket and lost it would certainly feel regret upon discovering that his ticket had the winning number, despite the fact that his loss was not necessarily the result of negligence. If the person however, was negligent, then merely regretting the loss without taking responsibility for his negligence would be insufficient.

  • Yoma 86b

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