Maimonides on Teshuvah


Maimonides on Teshuvah

The Ways of Repentance

Translation, Commentary, and Notes to Self

8th Edition (August 2020)

Commentary Revised during the Onset of the Coronavirus Pandemic

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Hebrew text, English translation and commentary, 316 pages.

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The Ways of Repentance    

Chapter One: Confession 

Chapter Two: Forgiveness                      

Chapter Three: Change                          

Chapter Four: Impediments                    

Chapter Five: Freedom                           

Chapter Six: Privilege                              

Chapter Seven: Teshuvah                       

Chapter Eight: Future                              

Chapter Nine: Present                             

Chapter Ten: Love                                   

My Father: A Tribute                               



“It is impossible to fulfill the obligations of the heart,” wrote Rabbi Avraham Isaac Kook, “unless one assembles a book that contains the teachings that inspire one’s own soul.” Maimonides on Teshuvah is my ongoing, yearly attempt to respond to Rabbi Kook’s spiritual charge.

My first draft, written some ten years ago, began as a simple translation of Moses Maimonides’ Laws of Repentance. I shared it with a few close friends, who encouraged me to make the text available more widely. I refreshed and expanded the commentary every year, pruning the obvious errors and adding minor insights, primarily for myself but glad for the company of other readers. After a few years the book became a kind of personal ritual of periodic self-examination, well-timed for the communal season of teshuvah that takes place in the early fall month of Elul.

In a way this book is a metaphor for the optimistic view I have of myself: full of personal failings and regrets, but with great capacity for change. Just as I delight in clicking “unpublish” on last year’s version and uploading a refined text, I hope that the same is true of my own personality, buffeted and bruised by the mistakes of the past but healed for a stronger, healthier future.

Dear Reader, I am grateful for your engagement in this yearly process. Teshuvah is an intensely private affair, conducted within the four cubits of one’s soul, demanding merciless, unflinching self-analysis. I certainly do not intend to take you to the darkest places of the cave, but it’s nice to stand with you at the entrance and point out the various passages I plan to explore on my own.

This year’s commentary was revised during the Coronavirus Pandemic, a global event with terrifying implications. My commentary this year includes several reflections on our current condition and what it means for the teshuvah process.

By long-standing Jewish literary convention, a Rabbinic approbation called a haskamah would appear at this point, assuring would-be readers of the scholarship and piety of the author (I am referring to my translation and commentary—Maimonides, of course, needs no approbation). I’ve elected not to seek an approbation for personal reasons. Readers should therefore approach this book with appropriate caution.

July 31, 2020


Lawrence, NY


Moses Maimonides is one of the towering figures of Jewish intellectual history. Among observant Jews he is known as “the Rambam,” an acronym for his Hebrew name, Rabbi Moshe ben Maimon (Moses son of Maimon), but in this work I will generally use the more familiar name “Maimonides,” Greek for “son of Maimon.” His reputation is encapsulated in the phrase inscribed on his tombstone in Tiberias, Israel: “from Moses to Moses, there was no one like Moses.”

Born in southern Spain in the 12th century, his family fled persecution and settled in Egypt, where he rose to prominence as a physician. He was an indefatigable advocate for Jewish causes around the world, working to rescue Jews taken captive during the Crusades and writing letters offering guidance and support to far-flung communities. His most famous works include The Guide for the Perplexed, a philosophical treatise explaining the foundations of Judaism, and the Mishneh Torah, a massive compendium of Jewish law. The Ways of Repentance (Hilkhot Teshuvah) is taken from that multi-volume work.

The title Mishneh Torah may be translated as “the repetition of Torah,” in the sense that it represents an ambitious restatement of the entirety of Jewish law, derived from both the Written Torah (the Five Books of Moses) and the Oral Torah (essentially, the Talmud). Maimonides’ stated goal was to collate and organize the thousands of details related to Jewish practice and thought scattered throughout these ancient sources and present them in a clear, straightforward fashion in a single work. A massive work of prodigious scholarship, his unified codification of Jewish law was written in a clear Hebrew style, free from literary flourishes but with great sophistication, accessible to students with even intermediate language skills. The Mishnah Torah became hugely influential even within his lifetime.

The Mishneh Torah also met with strong criticism from certain Jewish circles, particularly in Europe. Maimonides was bitterly censured for not providing detailed references to the Talmudic sources that informed his thinking (a lacuna that was filled by later commentators). More seriously, it was alleged that his deep engagement with classical Greek and contemporary Arabic philosophy had tainted the ideological purity of his Judaism. In one of the saddest episodes of Jewish intellectual history, French Jews denounced the work of Maimonides to the Church, and the Mishneh Torah was publicly burned in 1232.

The Ways of Repentance may also be rendered as The Laws of Repentance, as the Hebrew term halakhah is at once both “way” in the sense of “direction, means, method” and “law.” The term “law” suggests a level of coercion, and in fact Maimonides begins his book with the scriptural passage that contains the divine commandment to repent of one’s sins. The book, however, is far more concerned with the instrumental sense of the term halakhah, describing precisely how one might go through the process of repentance. Maimonides breaks down the challenge of confronting one’s own failings into manageable portions, and guides us through the process of careful rebuilding.

The Ways of Repentance has a place of distinction in the Mishneh Torah. Rabbi Mayer Twersky once pointed out that most of the Mishneh Torah is based on laws that exist in definitive places in the Talmud. The laws of the Sabbath, for example, are more or less represented in the Talmudic tractate Shabbat, the laws of Rosh Hashanah in tractate Rosh Hashanah, and so on. The laws of repentance, on the other hand, are not identified and concentrated in any single book of the Talmud. Maimonides recognized that these important teachings, dispersed throughout rabbinic literature, constituted a distinct group of laws that required a sustained analysis and codification. In this sense, Maimonides literally created the systematic study of repentance in Judaism. Moreover, as Rabbi Eliyahu Touger observed, in order to do this properly Maimonides had to extend the discussion into many theoretical areas such as the question of free will and the nature of the World to Come, making The Ways of Repentance a deeply philosophical treatise as well as a legal guide to proper behavior.

Maimonides is often difficult. He describes rigorous criteria for ethical development and inevitably we fall short. The risk of excessively negative and self-destructive thought is not insignificant. Rabbi Shlomo Wolbe, a major 20th century Jewish thinker, clarified such an approach to teshuvah is fundamentally flawed. Paraphrasing Deuteronomy 23:4, he argued that “depressive thoughts may not enter the congregation.” Rabbi Wolbe explained that teshuvah is essentially a joyous activity that consists of three distinct stages (citing Rabbi Israel Salanter, in Alei Shor p. 205):

The key and the beginning is the feeling (הרגש) that one has when learning the teachings of the Sages and texts of ethical wisdom, reviewing them time and time again until they act upon a person and cause one to sense one’s own personal flaws. Then one moves to the second level, which is the conquering of one’s inclinations (כבישת היצר). The third level is repairing one’s inclinations (תקון היצר) such that a person become joyous, and delights in the service of God.

How, exactly, does one manage to balance the serious work of discovering one’s character flaws with the putatively joyous activity of teshuvah? Rabbi Wolbe cites Rabbi A.A. Kaplan, who compares teshuvah to a father dancing while his young son sits on his shoulders. On the one hand, he dances with energy and vigor, wishing to please his beloved child, but at the same time he retains full consciousness of the precious weight on his shoulders, careful never to endanger his balance with a misplaced step. So too, we should enjoin the activity of teshuvah with seriousness, yet remain confidently joyful that the resulting improvements in our character will be meaningful, beneficial, and lasting.

This translation is based on the Frankel printing, which has become the standard critical edition. Passages edited out of the traditional edition, mostly due to the pressure of Church censorship, are included here and distinguished by the omission of vowels. I have added citations from the Hebrew Bible and the Talmud as necessary in parentheses. Gender-neutral language has been used whenever the translation would not suffer undue distortion. My intended readers are those who might not otherwise have the opportunity to study Maimonides in the original Hebrew, and therefore my commentary does not treat many of the important but abstruse Rabbinic debates over the meaning of the text in favor of a straightforward, uncomplicated explanation. Maimonides merely numbers his chapters; I have added titles to provide the reader with some sense of their content.

This classic work, almost a thousand years old, has much to offer the modern student of Judaism. The fourth chapter in particular deals with topics that have immediate and direct relevance to contemporary reality, and reads as freshly as the day Maimonides first composed it. Still, he wrote for an audience whose concerns were in many ways quite different from our own. Maimonides lived in a society where adherence to traditional Jewish law was the norm and not the exception, where distinctions of rights and privileges of the sexes were accepted, where polemics between Judaism, Christianity and Islam were prevalent, and the world of ideas was of deep interest to intellectuals beyond undergraduates in freshman philosophy class. A full appreciation for Maimonides’ genius and the spiritual insights of this book will only come after study, meditation, and review.

I conclude this introduction with a childhood memory, a thought I often turn to as I begin my personal, annual journey through Maimonides on Teshuvah.

Across the street from my father’s clothing store, and my childhood home in the apartment above it, ran a set of railroad tracks that once shuttled wood chips, sulfur and massive rolls of blank newsprint in and out of the paper  mill that sustained my home town of Iroquois Falls, Ontario. The locomotive crawled by several times a day, sounding its ear-splitting horn as it approached the unprotected intersection with the street. Even without boxcars, the train was so heavy that its passage shook the dishes in my mother’s china cabinet, a basso profondo roar that reverberated up and down my spine.

The sheer mass and power of the locomotive inspired respect, even fear. As a child, I often spent summer mornings placing pennies on the track, carefully noting the exact location of the coins by counting railroad ties from the street or marking the spot with a spray of purple fireweed. After the locomotive crawled past on its thunderous journey, I would hunt down the coins, now flattened almost beyond recognition—the faintest hint of Queen Elizabeth’s crown or a bit of the Canadian maple leaf were all that testified that the burnt orange disks were once legal tender. I would flip the distended coins over in my hands, testing their thickness and marveling at the incredible power inherent in the weight of the passing locomotive.

Imponderable though it was, the train was no match for the switches. Located about half a kilometer away, across from the IGA store, two parallel half-rails gracefully curved off the tracks, waiting patiently for the engineer to throw a lever and bring them into contact with the westward rails. Separated from the main line by tiny gaps no bigger than a finger, these tapered rails had the power to lead the massive beast away from its initial trajectory and cast it into the distant railway yards.

Sometimes, when I am not in a particularly charitable mood, I see myself as that locomotive, carrying an unimaginable weight of inertia through my quotidian life, mindlessly reacting to others around me according to long-established, maladapted patterns. Attempts to alter my behavior often feel quixotic and powerless, like pennies on the track, all efforts crushed and destroyed by their very first encounter with the weight of habit. Encouragement comes when I remind myself of those switches along the way, discreetly placed at key intervals, waiting for the signal from the engineer to connect them to the iron path and forever alter the train’s trajectory to a bold, unanticipated destination.

Maimonides’ The Ways of Repentance was one of the switches in my life. Reading it, and reviewing it, has helped me become the driver of my own locomotive, orienting my path whenever I found myself wandering away from my desired destination. I hope that you, dear reader, will gain similar benefit from this magisterial work.


    1. Hello Mr. Best!
      Just let me know who you’d like it made out to in an email ( I’m only autographing the pre-orders because after August 3 the books will come straight from the publisher. Thank you!

  1. Dr. Abramson :
    I am studying Hilchos Tshuva with a Chevruta by phone and came across your videos which are very helpful . I searched your book on Amazon and see it is currently listed for $855.oo for the paperback edition!! Can i purchase it directly from you? i called amazon and they may be fixing it but maybe you want to contact them also.
    thank you
    Sharon Glaser
    Edison, NJ

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