Anyone who has ever studied Mishneh Torah, from the novice student to the most advanced scholar, immediately senses Rambam’s unparalleled ability to organize and elucidate complex halakhic discussions from a wide variety of ancient texts and sources. This observation certainly holds true for Rambam’s ten-chapter discussion of the Laws of Repentance. The first chapter introduces the principle of teshuvah (repentance). The second chapter teaches how one does teshuvah. The third chapter explains how God judges a person and the difference between a righteous and wicked person. The fourth chapter lists 24 behaviors that prevent teshuvah. The fifth and sixth chapters, at the center of Hilkhot Teshuvah, extoll the principle of free will, which, for Rambam, is the basis of teshuvah. The seventh chapter teaches that repentance also applies to non-desirable character traits and how repentance can bring one closer to God. The eighth and ninth chapters discuss the rewards for following the commandments in this world and the World to Come and the goodness of messianic times. The tenth chapter teaches that even though there are a multitude of rewards for following the commandments, they should not be the primary reason for following the will of God. Rather, following God’s will should be based on love of God. In this chapter, Rambam defines what exactly is love of God, and it is thus a natural transition to the next book in Mishneh Torah, Sefer Ha-Ahavah, the Book of Love.
Notwithstanding the meticulousness and rational order of the chapters in Hilkhot Teshuvah, the fourth chapter seems out of place. Why exactly did Rambam feel it was necessary to enumerate these 24 items? What is especially interesting about this list is that it appears nowhere in the Talmud or anywhere else in tannaitic or amoraic literature. Already in Rambam’s own time, his readers were curious about the origins of the list and queried the Rambam about his source: “Of the list of 24 things that hold back teshuvah, is it a tosefta, or is it found in the Talmud?” Rambam answered that the list is not found “in the Gemara, the Tosefta, and not in the Sifra or the Sifri.” As the petitioner himself noted, Rambam’s only source for this list appears to be from the writings of Rif. Looking at the original quotation from Rif, however, will help us appreciate Rambam’s brilliance:
Twenty four things prevent teshuvah: gossip, derogatory speech, hotheadedness, bearing evil thoughts, befriending an evil person, partaking of a meal that is insufficient for the hosts, gazing at private parts, partnering with a thief, proclaiming I will sin and then repent, celebrating at the demise of a friend, separating oneself from the community, ridiculing one’s ancestors, ridiculing one’s teachers, cursing the public, preventing others from doing a mitzvah, influencing a friend to go in the wrong way, using the deposit of a pauper, accepted a bribe to influence a judgment, not returning a lost object, seeing one’s child going in the wrong direction and not protesting, eating the food of orphans and widows, arguing on the words of the wise ones, suspecting the innocent, hating criticism, [and] mocking the mitzvot.
It is readily apparent that Rambam used his unique genius to radically transform this citation. Rif simply lists 24 items that hold back teshuvah. Rambam rearranged the list, divided the items into five categories, explained why they each hold back teshuvah, and added the crucial caveat that “All of the above, and other similar transgressions, though they hold back repentance, do not prevent it entirely. Should one of these people repent, he is a ba’al teshuvah and has a portion in the World to Come.”
As opposed to Rif’s other commentators, Rambam felt that each item on the list must have a specific reason why it “holds back teshuvah,” as he went on to elucidate the reason for each. In contrast to this, Rav Hefetz, one of Rambam’s predecessors, simply suggested that these 24 items generally “distance oneself from God,” without explaining how exactly they “hold back teshuvah.“
Aside from demonstrating his organizational brilliance, one may still ask why Rambam felt the need to include this somewhat obscure rabbinic teaching in his meticulously organized Hilkhot Teshuvah. To answer that question, we need to look closer at some of the five categories listed by Rambam. The first thing one notices is that the majority of the sins in all five categories are related to sins between man and his fellow man, such as causing others to sin, or not returning lost objects. The few sins that on the surface don’t seem to fit into this paradigm have an interpersonal aspect as well. For example, the sin of gazing at someone’s private parts is certainly a sin between man and God, but it is also treating another human being as an object. In fact, the theme of the whole chapter is the relationship between the community and the teshuvah of the individual. Indeed, the only word repeated in the entire perek is kahal (community):
Therefore, it is proper for each and every community and community (kahal ve-kahal) in Israel to appoint a great sage of venerable age, with [a reputation of] fear of heaven from his youth.
I will say more on the significance of the word kahal later. With this insight, though, the first category of the chapter (“severe sins”) becomes readily understandable. The first three sins are all related to causing other people to sin, which, in the context of the chapter detailing the relationship between the individual and the community, is the severest of sins.
The one sin that does not seem to fit into this paradigm of severity is “saying I will sin and repent.” How is this related to causing other people to sin? I think Rambam himself answered this question. If one looks closely, there is an inward movement in the halakhah. It starts with the community, then your friend, then your child, and finally yourself. Teshuvah is hard to obtain in these cases because you caused, or are responsible, for the sins of others, and in order to receive atonement you have to repair your relationship with your community, your friends, and your children. Rambam’s beautiful insight is that you also have to repair your relationship with yourself to be forgiven. We can now also understand what Rambam means when he says, “God will not grant the person who commits such deeds to repent.” Rambam himself explains the phrase in his Commentary to the Mishnah (Yoma 8:7): “God will not help him do teshuvah.” The theme of the chapter is that a person does not live on an island and needs the help of friends, teachers, and community to do teshuvah. But one also needs the help of God, as He is also part of the community. The element of “measure for measure” now becomes apparent. If you cause other people in the community to sin, God won’t help you repent.
We can now also understand why, in the midst of a chapter listing items that hold back teshuvah, Rambam adds the halakhah (cited earlier) about each community needing to appoint a sage “to admonish the masses and motivate them to teshuvah.” The halakhah of tokhahah (rebuke) is, in its essence, about the responsibility of the community to prevent individual members from sinning, which is exactly the theme of the chapter.
Rambam makes one final important change to Rif’s list. While Rif listed these 24 things as categorically preventing teshuvah, Rambam (as I noted earlier) emphasized that even though the support of the community and one’s friends and teachers is extremely important in an individual’s journey towards atonement, it is not decisive. It might be hard and seem impossible, but a person does possess the ability to return on his or her own. This crucial point leads directly to Rambam’s next chapter, where he transitions from the community’s role in supporting and encouraging teshuvah to the responsibility of the individual.
One biblical character surprisingly makes a very brief appearance in this chapter:
One who demeans his teachers; this will cause him to reject and dismiss him as [Elishah did to] Geihazi.
Why did Rambam feel it was so important to mention Geihazi? What does his mention add to our understanding of the chapter? I think it is that his story encapsulates Rambam’s message in this chapter. To briefly summarize his story, Geihazi lied to his teacher Elisha about taking the spoils of war, and for that reason he and his children were punished with leprosy, which almost by definition cuts one off from one’s community (II Kings, chap. 5). In addition, the Talmud (Sotah 47a) teaches that Geihazi also prevented others from learning from Elisha. But the story doesn’t end there. In the continuation of that same passage from the Talmud, Rabbi Yohanan tells us that Geihazi and his three children were the four lepers who discovered that the Arameans had abandoned their siege. Because of their honesty in promptly reporting this, they wound up saving the people from starvation (II Kings, chap. 7). Their honorable actions enabled them to return to the community. This short story demonstrates Rambam’s teaching that it is possible even for a person cast off from his or her community to return to God. How was it possible for the estranged Geihazi to return? Rambam answers that question in the last halakhah of the chapter:
All of the above, and other similar transgressions, though they hold back repentance, they do not prevent it entirely. Should one of these people [adam] repent, he is a Baal-Teshuvah and has a portion in the world to come.
In other words, these items can hold one back, but not prevent one, from doing teshuvah. How does that work? The answer is immediately given in the first halakhah of the next chapter:
Free will is granted to all men [adam]. If one desires to turn himself to the path of good and be righteous, the choice is his. Should he desire to turn to the path of evil and be wicked, the choice is his.
Nothing, not even these 24 items, can overcome the will and free choice of a person. In the words of Rambam in the second halakhah:
Each person [adam] is fit to be righteous like Moses our teacher, or wicked like Jeroboam. [Similarly,] he may be wise or foolish, merciful or cruel, miserly or generous, or [acquire] any other character traits. There is no one who compels him, sentences him, or leads him towards either of these two paths. Rather, he, on his own initiative and decision, tends to the path he chooses.
When reading the chapter, one quickly realizes that the word adam (person) is very prominent. In fact, it appears 23 times. I would like to suggest that this corresponds to the 24 items that hold one back from doing teshuvah. Rambam is teaching that nothing can prevent a person using his or her free will from doing teshuvah.
If my supposition is correct, though, where is the missing adam to reach the number of 24? In the Frankel edition of the Rambam, the word adam is repeated in the second halakhah of the fifth chapter:
Each person and person (adam ve-adam) is fit to be righteous like Moses our teacher, or wicked like Jeroboam.
This repetition is not found in the standard Vilna edition. Not only does this addition create the numerical equivalence between the fourth and fifth chapters, but the repetition of the word adam parallels the repetition of the word kahal in the fourth chapter, echoing the respective themes of each chapter.
We can now understand both why Rambam included the list of 24 items in Hilkhot Teshuvah and the chapter’s placement within Hilkhot Teshuvah. The chapter highlights the importance of the role of community in the teshuvah process. Teshuvah has traditionally been viewed as a solitary experience of the individual standing before his or her Creator, but the crucial theme of the chapter is the vital role community can play in this process. Nonetheless, because of the awesome power of free will, even a man divorced from their community, for whatever reason, still has the ability to return to God. Rambam’s use (and reinterpretation) of Rif’s list of the 24 things that prevent teshuvah highlights this point and showcases his organizational brilliance and phenomenal creativity.
I would like to thank David Fried for his outstanding and professional help in editing this paper.
 Iggrot Ha-Rambam (Shilat edition) vol. 1, p. 209. Translation my own.
 Rif, Yoma 6a. Translation my own.
 All translations of Rambam are taken from https://www.chabad.org/library/article_cdo/aid/911898/jewish/Teshuvah-Chapter-Four.htm
 Rav Hefetz ben Yatzliah, quoted in Adiel Kadari, Studies in Repentance: Law, Philosophy and Educational Thought in Maimonides’ Hilkhot Teshuvah (Beersheva: Ben-Gurion University Press, 2010), 136.
 The last item Rambam enumerates beautifully encapsulates the whole theme of the perek, namely, don’t make friends with a wicked person because you will learn from his or her deeds. The community which includes one’s friends and neighbors should be a source of encouragement and inspiration to one’s spiritual and religious development, not an impediment.
 Rambam makes another change to Rif’s list:
…one who sees his son becoming associated with evil influences and refrains from rebuking him. Since his son is under his authority, were he to rebuke him, he would have separated himself [from these influences]. Hence, [by refraining from admonishing him, it is considered] as if he caused him to sin.
The implication of Rambam’s formulation is that if the rebuke would not be effective, there is no obligation to rebuke. This addition could be of tremendous consolation to parents dealing with wayward and searching children who know in their hearts that rebuke is not the best method to reach their children and return them to the fold.
 In the Frankel edition, Jesus is also mentioned in addition to Geihazi. Rambam probably bases this addition on Sotah 47a, where Jesus is mentioned. It would be interesting to look further at Rambam’s use of biblical characters in his Mishneh Torah.
 If one were to assume that the Vilna text is correct, one could suggest that the missing adam is in the last halakhah of the previous chapter quoted above, “Should one of these people [adam] repent, he is a ba’al teshuvah and has a portion in the world to come.” This would serve to connect the two chapters. The key is that a person can rise above his or her circumstances and return to God at any time or place, even without the help of his or her community. Rambam was certainly aware of the phenomenon of counting words to create meaning, as this technique is used in the Talmud . It would be interesting to see if Rambam consistently used repeated words to create meaning. One can see another example in Hilkhot Megillah ve-Hanukah, chapter 4, where the word bayit (house) is repeated. My article on this is available at: https://etzion.org.il/en/holidays/chanuka/chanuka-holiness-temple-and-home
One can also suggest that the repetition of the word adam is related from another perspective to the theme of the chapter. There is a recurring duality in the chapter, e.g., between life and death, blessing and curse, and wise and foolish, which is a reflection of the choice given to every person to be good or evil. Thus, the crucial question of the chapter is what kind of adam does a person want to be? The repetition of adam serves in a literary sense to highlight this stark choice and opportunity given to every person.