The Mishnah in Tractate Yoma [8:9] takes us on a deep dive into the laws of repentance. The Mishnah tells us “One who [sins and] says: I will sin and then I will repent, I will sin and then I will repent, an opportunity to repent is not given to him. [If one says:] I will sin and Yom Kippur will atone for me, Yom Kippur does not atone for him”. This week we’ll peer into the mechanics of these laws. Why does a person who relies upon future repentance not merit expiation for his sins? What has he done wrong?

The Talmud [87a] addresses this question. Noting that the Mishnah says “I will sin and then I will repent” twice, the Talmud teaches that the fact that this person commits the same sin multiple times means that he no longer considers the action sinful and hence he will not be inclined to repent. The Talmud is teaching that the barrier to repentance is not a punishment, but, rather, a direct psychological result of a person’s actions. While this person is always able to repent, he will more than likely not take advantage of repentance.

Rav Yoshiyahu Pinto, writing in his commentary on the “Ein Yaakov”, itself a commentary on the Aggadic portions of the Talmud, notes that the Mishnah does not say “I will sin, I will sin”. It adds the words “…and then I will repent”. Therefore, Rav Pinto asserts that the only feasible chain of events is if the person has sinned, repented, and then sinned again. After he sins for a second time he will not be given an opportunity to repent a second time. It seems that Rav Pinto is continuing down the same psychological path advanced above: A person has already sinned once and then repented. If he commits the same sin a second time, simultaneously promising to repent for this sin at some future date, it is clear that he is committing this action because he does not believe that he is doing anything wrong.

While the psychological hypothesis has a certain appeal, it is lacking in that it does not adequately address the second case in the Mishnah, the person who sins with the assumption that Yom Kippur will atone for his sins. There is no self-deception here – this person knows full well that he is sinning. Further, our sinner is standing on solid halachic ground: The Talmud in Tractate Yoma [85b] teaches that Yom Kippur has the power to negate sins even for one who does not repent. Moreover, our sinner knows that Yom Kippur is the most cathartic day of the year. He knows that very few people can step into a synagogue on Yom Kippur and not feel pangs of guilt that have the power to elicit a real, albeit ephemeral, desire to change. So if he knows that when Yom Kippur comes he will truly be remorseful for his deeds, why is he not forgiven when the remorse actually comes?

The Rambam makes our life more difficult. Writing in Hilchot Teshuva [4:1], he rules “There are twenty-four deeds which hold back repentance… d) One who says: ‘I will sin and then I will repent.’ Included in this category is one who says: ‘I will sin and Yom Kippur will atone [for me].’” Notice that the Rambam has taken the person who says “I will repent sometime in the future” and the person who says “I will have a cathartic Yom Kippur” and has lumped them into one example, essentially stating that these two people suffer from the same flaw. Worse, the Rambam seemingly misquotes the Mishnah, repeating the words “I will sin and then I will repent” only one time, refuting the Talmud’s psychological explanation. It must mean that the Rambam has a different understanding as to why these two people do not merit expiation of their sins[1].

The explanation that follows sprouted from a shiur by Rav Ezra Bick on Parashat Nitzavim. Parashat Nitzavim begins with Hashem making a covenant with Am Yisrael. Rav Bick, noting that a covenant – the tochecha (admonition) – has already been entered only one chapter earlier, asks why it is necessary to enter yet another covenant. Basing himself on the explanation of “the finely tuned ear” of the Netziv of Volozhn, Rav Bick explains that there is a seminal difference between the covenant entered in Parashat Nitzavim and the tochecha. The tochecha is simple: Do good and you will be rewarded, do bad and you will be destroyed. The covenant in Parashat Nitzavim is different: it asks for commitment, it asks for love. The tochecha speaks to the mind. This covenant speaks to the heart. It is an entirely different covenant.

Between 1685 and 1686, Sir Isaac Newton wrote Principia Mathematica, a ground-breaking book that became the Bible for the Laws of Motion. Without Principia Mathematica the Industrial Revolution could never have transpired. The laws introduced by Newton remained unchallenged for more than two hundred years until Albert Einstein came along with his Theory of Special Relativity and changed everything. Einstein took Newton’s Laws of Motion and added one constraint: The speed of light in a vacuum is the same for all observers, regardless of the motion of the light source[2]. If a spaceship flying half the speed of light turns on its headlights, the speed of the light coming from the headlights is still 3.0 x 108 meters per second, same as for a stationary spaceship. I remember sitting in my first Physics class in the Technion, watching with amazement as the professor used something called the “Lorentz Transformation” to roll this constraint into Newton’s Laws of Motion and out came Einstein’s Laws of Motion. The two look very similar, except that Einstein’s are littered with a symbol called β, defined as v/c, the velocity of an object in motion divided by the speed of light. For an object travelling much slower than the speed of light, β is very close to zero and Einstein’s equations morph into Newton’s. But when the velocity of an object nears the speed of light, weird things begin to happen: things get bigger and heavier and time slows down. For instance, if an astronaut flies off to visit a nearby star at ninety percent the speed of light, he will return to earth nearly ten years later but he will have aged by less than half that much. Special relativity is an indispensable tool of modern physics and its predictions have been experimentally tested repeatedly without discrepancies.

A midrash in Tractate Makkot of the Jerusalem Talmud [2:6] tells how “Wisdom was asked what should be the punishment of the sinner? It answered: ‘Let evil pursue the sinners.’ Prophecy was asked what should happen to the sinner? It answered: ‘The person who sinned should die’. The Torah was asked what should be the punishment of the sinner? It answered: ‘Let the sinner bring an offering and be forgiven’. Finally, Hashem was asked what should be the punishment of the sinner. He said, ‘Let the sinner repent and he will be forgiven.” The midrash is teaching us that repentance defies the rules of morality as defined by the Torah. There should be no way that a person can undo, either physically of spiritually, his misdeeds. What happened cannot be changed. And yet, Hashem has devised a legal system in which repentance is not only possible, it has been proven highly effective.

The Rambam rules that the problem with the person who says “I will sin and then I will repent” is the same problem with the person who says “I will sin and Yom Kippur will atone for me”. The problem is not psychological, it is procedural: both of these people are attempting to implement laws of morality where they are not applicable. If the topic at hand were damages or Kashrut or Shabbat, then logical halachic constructs might contain a certain amount of validity. But repentance operates by a different set of rules and by a different kind of logic. To paraphrase the Netziv, repentance operates from the heart and not from the mind. Rules that apply for the other six hundred and twelve mitzvot do not apply when it comes to repentance. To paraphrase Einstein, if someone tries using Newtonian physics fly a spaceship near the speed of light, that spaceship is going to crash because this person is using the wrong set of equations.

Hashem has blessed us with the supernatural ability to throw away our past and to start over again. The only caveat is that if we want repentance, then we have to gain it on His terms.


Shabbat Shalom and Gmar Chatima Tova,

Ari Sacher, Moreshet, 5778

Please daven for a Refu’a Shelema for Yechiel ben Shprintza and Tzvi ben Freida.

[1] See the Lechem Mishna and the Yad Peshuta for an explanation of the Rambam.

[2] “3.0 x 10 8 meters per second: it’s not just a good idea – it’s the law”.