Why Does Teshuva Require Tzedaka?

Chazal and the Rishonim and the Achronim make it clear that Tzedaka has a role in Teshuva. We are going to analyze the relationship of Tzedaka to Teshuva. But please, do not lose sight of the forest for the trees. Do not let the Yetzer Hara cheat you out of an effective and meaningful Teshuva. Shedding tears and sincerely klapping Al Chet is not enough. You need to remember that Tzedaka is a vitally important part of Teshuva.

I am very grateful to Harav Shimon Kalman Goldstein for bringing up this excellent question. Remarkably, I have found almost nobody talks about it.

Let’s put Unesaneh Tokef to the side for a moment.  The Rambam in the second perek looks at Teshuva from three perspectives

2:1 –

What is “Complete Teshuva”? When the opportunity to sin presents itself and he rejects it.

2:2 and 3 –

What is (the process) of Teshuva? Leaving the sin, not thinking about how nice it would be to sin, a decision to never sin, and regret for the past. The resolution has to be so firm that God Himself will testify that he will never do this sin again.

Teshuva requires Vidui. Vidui must specify what sins you are doing teshuva for, and it must verbalize an absolute resolution to never sin again.

2:4 –

The “Ways of Teshuva” are tearful prayer, Tzedaka to the extent he is able, rigorous avoidance of the opportunity to sin, changing his name (as if saying “I am no longer that sinful man, I am a different person,”) and exile (because exile brings forgiveness by making a person feel humble and lowly.)

Here the Rambam has introduced something new.
He told us what proves full Teshuva in 2:1.
He already told us how to do Teshuva in 2:2 and 3.
What is he telling us now in 2:4? What does that mean, מדרכי התשובה? What is the meaning of “the ways/paths/behaviors of Teshuva?” Is it part of Teshuva or not?

In the next perek, 3:4, he says the specific association of Tzedaka with Teshuva is common knowledge and universally observed.

The Rambam’s association of Tzedaka with Teshuva and Kapara appears in many places in Tanach and Chazal, which is why it is common knowledge.

We know this from the words of the Navi Yeshaya (58,)

And from what Daniel told Belshatzar in Daniel 4,

Additional mekoros for the Rambam are the Gemara and the Yerushalmi/Medrash Rabba.
RH 16b-

Yerushalmi Taanis 2:1 and MR Breishis 44:12.

Tzedaka figures prominently in the idea of Teshuva and Kapara.  But why? We all understand that Teshuva brings Kapara. What does Tzedaka have to do with Teshuva and Kapara?

Is it because כל המרחם על הבריות מרחמין עליו מן השמים so it protects from punishment, or does it somehow erase the aveira, as Teshuva does? Is it direct, or indirect? Is it for Teshuva, or is it for Kapara, or is it for Ritzui?

In proper English: Punishment for a crime, or a sin, might be avoided in two ways – Pardon and Expungement.  A Pardon grants forgiveness. It does not erase the event, it only means that the person, or the society, that had a claim against the malefactor no longer seeks to punish or penalize him. Expungement, on the other hand, erases the criminal act. It is as if the event never occurred.

Here is a perfect example of what being a Baal Chesed can do. In some cases, after a person has been found guilty, the judge has discretion in determining the sentence. Often, a judge will allow letters of character to be submitted to the court, and such letters can carry substantial weight in his decision. He might mitigate the sentence significantly, or at least incline toward the lower end of the sentencing guidelines.

By Aveiros, it would be a great chesed if the punishment alone were removed or mitigated, and that is what comes to mind when we think about the Rachamei Hashem that is evoked by Tzedaka.  The avaryan, through showing mercy to others, is shown mercy as well, and the punishment he earned is mercifully set aside.

When we talk about Teshuva, we think about Expungement, מריקת ועקירת החטא. Tzedaka and Chesed, on the other hand, would seem to have an effect of Pardon, הגנה מן היסורין וכפרה. So in what way is Tzedaka related to Teshuva?

Besides the very important difference in hashkafa, here’s another obvious nafka minah. If it’s because כל המרחם, then it falls under the regular rubric of Tzedaka, and so the usual rule of אל יבזבז would apply. If it is directly related to the din of teshuva, then the idea of צדקה כפי כחו  would mean he should do whatever is possible for him to do in order to get kappara, and אל יבזבז would not apply.
Poskim do discuss this issue, of whether אל יבזבז applies in this case. I have not seen any that make what seems to me to be a clear cut tliyah.

I have organized the answers into FOUR basic approaches. There are important variations within each.

1. Tzedaka is an adjunct to Teshuva.
A. Tzekada is completely unnecessary for Teshuva for most sins because Teshuva alone is effective. Only in special cases, where Teshuva alone is not sufficient to eliminate the consequences of the sin, (i.e., Kareis and Missas Beis Din,) will Tzedaka become necessary as a “booster,” or a supplement.  This is clearly not like the Rambam who applies it to all cases.
B. Special effort for Tzedaka is an “echo” that follows Teshuva – that Teshuva ought to create a special desire for Ritzui and Dveikus (perhaps to bring you closer to the darga of תשובה מאהבה,) and the way to bring that about is through Tzedaka.
(Rabbeinu Yona in Sha’arei Teshuva and Peirush on Mishlei; (brought below, preceding the numbered answers).)

2. Tzedaka is the vital prerequisite to Teshuva. It is not itself Teshuva, but it is an essential threshold to doing Teshuva.
The forgiveness brought by Teshuva is not an entitlement.  It is a gift granted when Hashem acts with Middas HaRachamim. Only a person that is himself a rachaman is granted Middas HaRachamim.  (In a range of variations – Chafetz Chaim in Ahavas Chesed and as quoted by Rav Friedlander in Sifsei Chayim (Section I of End-Note), the Netziv in Ki Savo (1), and the Leket Yosher (4).)

3. Tzedaka is a part of Teshuva – it helps erase the aveira.
A. Because giving Tzedaka nullifies the apikorsus that lies at the root of every aveira. It is an antidote to the underlying disease of aveiros. (Harav Shimon Kalman Goldstein  and R Avrohom ben HaRambam (2).)
B. Because it is like a Korban. (Rashi and Rabbeinu Bachaye (3).)
C. Because you can’t disentangle yourself from self indulgence and impulsiveness without taking actual steps of selflessness and hispashtus from Gashmiyus through chesed.  (Rabbi Moshe Eisenberg  and R Avrohom ben HaRambam (6).)
D. The effect of an Aveira on your soul depends on the purity of your soul. An essential purity will protect you the Tuma effect of the Aveira.  (Section II of End-Note, from Sifsei Chaim.)
E. Teshuva alone does not erase the sin of the past. That requires either Teshuvas HaMishkal, or that you learn Torah and do Gemillus Chasadim. Torah and Gemillus Chasadim, as part of Teshuva, are more effective than self-mortification. (The Gaon in his Peirush on Mishlei, (8).)

4. Tzedaka is, in a sense, a part of Teshuva because Teshuva has two steps:  First you must eliminate your wicked past. AFTER eliminating your wicked past by doing Teshuva, you have to re-create your better future self. Creating a “Bein Adam LaMakom Tzadik” while ignoring Bein Adam l’Chaveiro produces a monster, not a Tzadik, and your Teshuva will accomplish nothing permanent, like a זורע ואינו קוצר.
(R Micha Berger (5), R D Gary Schreiber (7), and the Ritva in Rosh Hashanna (9), and possibly Rabbeinu Yona in his first answer in Mishlei.)