One of the great principles of teshuva is that it is not a right but a privilege, an act of mercy which defies natural law. Mesillat Yesharim puts it as follows:

According to strict justice, there should be no correction at all for a sin, for in truth, how can a man straighten that which he has made crooked, when the sin is already done? If a man murdered his neighbor ... how can this be corrected? Can he wipe out the act from existence? ... Rather, repentance is granted to sinners as an act of pure lovingkindness, so that the cancellation of the will be considered the cancellation of the act.

In other words, history is history. Even if regret itself is worthy of approval and reward, it should not have the power to erase the actual transgression. In fact, human justice embodies this very principle. Once a crime has been committed, the mere expression of regret and repentance does not suffice to protect the criminal from conviction (though it might be a mitigating factor when meting out punishment). Repentance, then, and its ability to wipe the slate clean and return a man to a state of innocence, belongs not to the realm of justice or law, but to that of mercy. God, in His infinite grace, redeems undeserving man from the results of his own actions, relying on his change of heart ("the cancellation of will") to effect a change in history ("the cancellation of the act").

Rav Elchanan Wasserman (Kovetz Maamarim, p.23) posed the following question to the Chofetz Chaim concerning this principle: The Gemara in Kiddushin (40b) states that even one who was righteous all his life can lose all merit if he rebels at the end. The Gemara asks: Should he not be considered as having a mixed record; i.e., have his mitzvot count, with the sin of his old age added to the record. "Resh Lakish said: This refers to one who doubts the earlier actions (i.e., he regrets the mitzvot he performed)." We see here that regret obliterates the mitzvot performed as though they never occurred. Since mercy and grace are not at work here, does this not indicate that it is justice which demands that regret cancel good deeds? If so, it should surely cancel sins by the same token.

Rav Elchanan records that the Chofetz Chaim answered that it depends on the nature of the teshuva. The Gemara states that teshuva me'ahava (repentance out of love; i.e., heartfelt regret) results in the transgressions being transmuted into merits, whereas teshuva miyir'a (repentance out of fear) results in transgressions being transmuted into shegagot - unintentional lapses. Justice indeed requires that one who genuinely regrets his actions not be held accountable for them; however, that the transgressions be considered as merits is an act of pure mercy. Hence, one who does teshuvah me'ahavah is forgiven out of justice, and mercy is required for him only in order to reach the higher level where his sins are transmuted into merits. On the other hand, one who simply fears imminent punishment but does not genuinely regret his misdeeds, has no claim to justice and the efficacy of his teshuvah is completely dependent on God's mercy.

Rav Elchanan rejects the applicability of this answer to the statement of the Mesillat Yesharim, which indicates that even one who has completely and sincerely regretted his actions requires the attribute of mercy in order for his repentance to be effective. Rav Elchanan therefore suggests another answer, based on a distinction of the author of the Mesillat Yesharim in another section. All mitzvot and all transgressions have two aspects. The first is that they represent obedience or rebellion vis-a-vis the word of God. This is expressed in the Talmudic statement that one who is commanded and performs a mitzva is greater than one who volunteers. The second is the positive or negative influence that the action has on his soul. Every commandment of God has a value and effect for the one who performs it. Rav Elchanan suggests that logically, regret corrects the aspect of sin whereby one has rebelled against God. Having repented, one's relationship with God can return to its earlier pre-rebellion state. However, the actual consequences of the act are unaffected by one's psychological regret. Here, the miraculous mercy of God shines forth, and He repairs the damage to the sinner, to his soul, and to the world, granting him atonement and purification as a response to his repentance.

The distinction on which Rav Elchanan bases his answer is central to the idea of repentance, and is in fact implied by the answer of the Chofetz Chaim. Sin is not merely the cause of God's displeasure with the sinner. It is a stain, a corruption, in the soul of the sinner. Repentance is not merely mending one's fences with God, but, in the similes used by Tanakh and Chazal, it is cleansing, purification, catharsis, and healing for the sinner who is defiled, impure, corrupt, diseased. It is precisely this aspect of sin which requires the transformation into merits mentioned in the answer of the Chofetz Chaim. Shegagot - unintentional acts - are not deserving of punishment. God forgives them. But they nonetheless leave their mark. Ramban, for instance, states that apparently undeserved suffering is intended to cleanse man of the impurities in his soul caused by unintentional transgressions. This idea is also portrayed in a midrash about Avraham Avinu:

Your people come forward willingly on the day of your battle; in majestic holiness, from the womb, from the dawn, yours was the dew of youth (Ps. 110:3)".... Yours was the the dew of youth - For Avraham Avinu was anxious, saying: Do I bear a sin, since I was an idol worshipper all those years? God said to him: Yours was the dew of youth - just as the dew evaporates, so your sins evaporate. (Bereishit Rabba 39:8)

Avraham knew that since he had repented, he had no reason to fear being punished for his early sins. The idolatry of Avraham's youth was, in any event, the result of his upbringing. Halachically, he was the classic tinok shenishbah, literally brought up among the heathens, whose status is that of shogeg. But Avraham was anxious about the residual stain upon his soul; he felt a heaviness which weighed him down. Hence the promise, not of forgiveness in the usual sense, but evaporation, returning Avraham to the unsullied state of his youth. This Avraham did not expect,for it is not a logical, natural process, but rather one of grace and mercy.

Presenting this aspect of teshuva in the character of Avraham is important, for Avraham is Avinu, the archetype of a Jew. Rejuvenation is hence the hallmark of our relationship with God. The Midrash depicts rejuvenation as the central symbol of Avraham: "Avraham's 'coin' was circulated in the world. What was his coin? An old man and woman on one side, a young man and woman on the other" (Bereishit Rabba 39:11). The aspiration to freshness and purity is much more than a desire to escape punishment or rejection. This everlasting hope to return to the dew of one's youth even after years of weary toil and defeat is an integral part of the Jewish experience from its inception.

Rav Hutner (Pachad Yitchak, Rosh Hashana, 74) advances a different answer to the question. He explains that the Gemara in Kiddushin does not support the conclusion that regret can cancel sin in any sense, for the paths leading from evil to good and that leading from good to evil are not analogous. The Torah teaches us that the dichotomy of good and evil is equivalent to that of life and death. The evolution of life into death is a natural, universal phenomenon. However, the opposite is unknown, so much so that techiyat hameitim, the resurrection, is considered the greatest of all miracles. Life must be constantly supported with food, water, and air, whereas death is a self-sufficient state which requires no effort to maintain. The same is true of good and evil. Good, even after it has come into being, must be sustained, else it loses its vitality and progressively decays. The food, the sustenance, of good, Rav Hutner teaches, is the faith of man in its value. A man who regrets the good he has done, who no longer believes in it, destroys its foundation of existence in this world of natural law. The opposite is not true, however. Like death, evil, once it comes into existence, will continue to exist by means of inertia, and there is no natural way to transform it. Only God's infinite power and mercy can restore life where once it has been removed, and replace evil with good. Hence, teshuva depends totally on God's grace.

Rav Hutner's explanation highlights the extraordinarily precarious nature of good. True, we believe that good comes from God and that ultimately evil has no basis in reality. In this world, however, a world of natural law separate from God, good can only exist where man, the image of God, struggles to give it life by investing reality with his faith, his effort, and his commitment. One of the attributes of God (for instance in the conclusion of Yishtabach), is "chai" - life, meaning that God is life itself and all life requires the presence of God to support it. Sin is death because it drives a wedge between God and the sinner. It is not difficult to cut off something from life; hence the tzaddik can negate a lifetime of virtue in an instant. To recreate a connection to life, transcendance is required. "Great is teshuva," state Chazal, "for it reaches up until the throne of glory." It must reach up until the throne of God or else it will be ineffective in resurrecting the tired souls, the dying and the dead. On the other hand, even inattention, apathy, or loss of faith is sufficient to undo the good that already exists. It is a law of nature that any system left uncared for will become chaotic and any organism left unfed will tend toward death. Even great accomplishments of the past will stagnate and decay if they are not continually supported by the faith and the efforts of man. In God's world, all is life; in this world, life can only exist where man brings the name of God.

May it be His will that we be inscribed for a year of life and redemption, for us and all Yisrael.