Nitzavim, Devarim 30:2. ושבת עד ה'.... בכל לבבך ובכל נפשך ושב ה' אלוקיך את שבותך וריחמך Teshuva on Aveiros and Teshuva on Mitzvos.

Our parsha mentions the concept of Teshuva.  Teshuva might be one of the Taryag Mitzvos (Ramban here), or it might be too fundamental to be called a mitzva (Minchas Chinuch 364 explaining the Rambam in the Yad).  In any case, our pesukim are talking about Teshuva, and they tell us that teshuva can be doubly effective, that it not only ends punishment, but that it can also bring us to a state of grace and love and blessing.

The Mesilas Yesharim (perek 4) says that Middas Hadin, the Divine Attribute of Strict Justice, would not allow for Teshuva.  Under Middas Hadin, the punishment for a sin would be immediate and devastating, and the sin would be irreparable.  It is only through Middas Harachamim that these consequences are ameliorated.  The sinner is given time to repent, the punishment is diminished, and Teshuva  uproots and erases the sin entirely.  This modification of Middas Hadin is only possible through the Chesed, the charity, of Middas Harachamim.  (I've included the Hebrew and English text of the Mesillas Yesharim at the end of the post.  It's Elul, it's time to look at the Mesillas Yesharim.)

Reb Elchanan Vasserman asks the following question from the Gemara in Kiddushin 40b (which is also brought in the Rambam 3 Teshuva 3).

ר"ש בן יוחי אומר אפילו צדיק גמור כל ימיו ומרד באחרונה איבד את הראשונות שנאמר (יחזקאל לג) צדקת הצדיק לא תצילנו ביום פשעו ואפילו רשע גמור כל ימיו ועשה תשובה באחרונה אין מזכירים לו שוב רשעו שנאמר (יחזקאל לג) ורשעת הרשע לא יכשל בה ביום שובו מרשעו וניהוי כמחצה עונות ומחצה זכיות אמר ריש לקיש בתוהא על הראשונות

Briefly:  A life-long perfect tzadik that rebels at the end of his life loses all that he has done in the past.  Reish Lakish explains that this is not true if he sins out of some momentary desire or weakness.  It is true only when he recants and regrets his good deeds-- he is toheh ahl harishonos.  

From this Gemara we see that natural law mandates that regretfulness for past mitzvos erases all the mitzvos.    Reb Elchanan (Kovetz Maamarim, Ahl Hateshuva, p 21) asked the Chafetz Chaim, How then can the Mesillas Yesharim say that the power of Teshuva to erase past sins is a gift arising from Middas Harachamim?  According to the Gemara, regret is a natural and universal solvent: if you regret good acts, the good is erased.  If that's the case where the result is suffering and punishment, then kal vachomer (Meruba middas tova mimidas puranus) the same would naturally be true in the opposite regard- that regret for sin will erase the sins and prevent punishment.  Why does the Mesillas Yesharim say that the ability of Teshuva to erase sin is a singular and unparalleled gift from Hashem?

(Some people answer that only after the gzeiras hakasuv that Teshuva erases sin did it follow that Toheh ahl Harishonos erases mitzvos.  With all due respect, I think that's just infantile, a reflexive ‘lomdus’ that doesn’t make any sense.  The latter does not follow the former at all.  The protocol of Din does not have to echo that of rachamim.  That's the whole point of saying that midda tova is meruba.)

The Chafetz Chaim  answered that while it is true that all regret erases past behavior, Teshuva is unparalleled in two ways.  1. Teshuva brought about by fear of punishment does not mean that the baal teshuva regrets his aveiros like the Toheh, the sinner in Kiddushin, regrets his mitzvos.  A man who is doing Teshuva out of fear only regrets the deadly consequence of his sins.  Despite his lack of true regret, Teshuva meiYira erases his sins.  2. And if the Teshuva was from love of Hashem, Teshuva meiAhava, it doesn't erase the sin- it reconstitutes the sin into a meritorious act, as if it were a mitzva.  This is  unparalleled in the case of one who regrets having done a mitzva, and is the unique result of Middas Harachamim.

Reb Elchanan points out that the Ramchal's words do not seem to accord with the Chafetz Chaim's pshat.  The Ramchal said that even the erasure of sin is only possible because of Middas Harachamim, while the Chafetz Chaim said that erasure of any past mitzva or aveira is the natural result of charata, of regret. Also, Charata is Charata. If it works by toheh, it should work by teshuva meiyirah.

Reb Elchonon himself distinguishes between aveiros that are tzivuyim and aveiros that a pogem your neshama. The former are no different than toheh. The chiddush of teshuva is that it works even by the latter. Or, as some say in Reb Elchonon, that changing your identity from Rasha to Tadik or vice versa is not a chiddush. The only chiddush of teshuva is that it changes the past. (That which the Gemara says that Toheh loses schar, that is because a rasha can not get schar for mitzvos that he did.)

Rav Yosef Gavriel Behchhoffer offers a fascinating suggestion to answer the question. Rashi there says 

בתוהא - מתחרט על כל הטובות שעשה. R YG wants to say that Toheh is only where he regrets EVERYTHING good that he has done. This naturally results in losing his schar and his status. The chiddush of teshuva is that it works even when he does teshuva on ONE AVEIRA. That aveira is nimchal and erased and, if mei'ahava, the past becomes mitzvos instead of aveiros.

https://youtu.be/e8_r_YB9AVc?si=rlUi3QVETpJHKrE7&t=616

I'd like to point out that my reading of the pesukim in Yechezkel, both the pasuk brought in Kiddushim from perek 33 and also the passuk in Yechezkel perek 18 brought in Yoma 86, indicates to me that just as Teshuva can change aveiros to mitzvos, exactly so can Toheh ahl Harishonos, regret for past mitzvos, change them into Aveiros.  And it's not only my reading.    The Arvei Nachal (by the author of the Levushei Srad and the Tiv Gittin) on Parshas Va'eschanan Drush II, says exactly that.  This, too, does not seem to accord with the words of the Chafetz Chaim.

Also, I wonder, what kind of Toheh is the Gemara in Kiddushin talking about?  Is it talking about a Toheh that matches the Teshuva we are told to do?  Is a man called a Toheh only if he deliberately and thoughtfully reexamines the mitzvos he did, is deeply ashamed of them, mournfully regrets doing them, and makes a firm conscious decision to never do mitzvos again?  Does he have to re-create himself, as the Rambam says of the Baal Teshuva?  I doubt it.  It means just what it says:   that he regrets having done the mitzvos.  If that's enough to erase mitzvos, why wouldn't similar regret be enough to completely erase aveiros?  Why does teshuva require the wrenching effort of בְּכָל לְבָבְךָ וּבְכָל נַפְשֶׁךָ?

Unfortunately, this all seems to point toward something I've often quoted from a well known and highly respected Mashgiach that I've had business with.

 "Good Comes and Goes, but Bad is Forever."

He didn't put it in those exact words, but pretty close, and I think the aphorism sums up his philosophy, that a spiritual fall generates an indelible change that forever increases the risk of relapse. Spiritual advances, on the other hand, are fragile, easily lost, and effortlessly extirpated. They disappear easily, and when they do, they don't leave a trace.

Reb Yitzchak Hutner in his Pachad Yitzchok answered Reb Elchonon's question along the same lines (minus the cynicism.)  He said that going from life to death is part of the teva, the natural order of Hashem's universe.  Going from death to life is not.  Order requires constant energy, while disorder is the default state.  Anyone can be meimis a chai.  Not everyone can be mechayeh a meis.

Another way to put this: Middos Ra'os take root much more easily than middos tovos.  Uprooting them is much harder than uprooting good middos.  What is true for Middos is also true for the effect of mitzvos and aveiros.  That alone would serve to explain why Toheh is derech hateva, while Teshuva is lema'ala miderech hateva.  Besides being painfully obvious, the Beis Yosef in the beginning of Orach Chaim says this about Azus Panim. Bad behavior is dyo, an indelible dye, while good behavior is sikra, faint and superficial.  One would think that observing disgusting behavior is not likely to influence you to emulate that behavior.  But in our parsha, in 29:16, it says that if you observe the disgusting pagan rites, beware of the effect on you, and know that you might be influenced by it.  Similarly, the Gemara (beginning of Sotah, brought by Rashi in Ki Sisa) says "haro'eh sotah b'kilkula, yazir atzmo min hayayin."  If you see a Sotah ugly disheveled and publicly disgraced, be on guard!  You are in danger of following her example.  Avoid wine!  Thus, we see that the result of Toheh is natural, while Teshuva is practically a miracle.

But one can say another mehalach.  And do me a favor: after reading it, the teretz is obvious.  But it wasn't obvious before you read it, so don't give me a hard time.  Hakol b'chezkas sumin....

Toheh works like Kavana misnagedes in mitzvos (Rosh Hashanna 28).  Even if you hold Mitzvos einan tzrichos kavana, that is because (as Reb Moshe says in the Darash on Ushmartem es hamatzos, Shmos 12:17) stama lishma , or because if the person realized that he had done the mitzva he would be pleased, or because of the Rambam in the second perek of Hilchos Geirushin.  But certainly, the desire to do Hashem's will is fundamental to all mitzvos, and if you do the mitzva intending that it not be a mitzva, you have done nothing at all.  For aveiros, on the other hand, even if you do an aveira with kavana misnagedes, for example, you do the aveira because you enjoy it but have kavana davka not to transgress Hashem's will, it doesn't make a bit of a difference, you're still punished for the aveira.  And worse than that: when one does a mitzva and davka doesn't want to be mekayeim Hashem's will, the act of doing the mitzva is the biggest moreid bemalchus.  Of course his mitzvos turn into aveiros.

With these teirutzim we can answer a kashe on a Tosfos in Sanhedrin 37b.  The Gemara says that even though our courts are no longer empowered to administer capital punishment, Hashem makes sure that the appropriate punishment occurs.  Tosfos asks, but we see many people who deny the entire Torah who live and prosper?  Tosfos answers that perhaps their Bris Milah suspends their punishment and they are given the reward for that mitzva before they die.  The problem is that obviously these people are Toheh.  If so, then according to the Gemara in Kiddushin they should get nothing at all for their mitzvos!  But according to our teirutzim, there is no kashe.  Tosfos chose the mitzva of Millah very carefully, because Millah is different than all other mitzvos.  The din of Toheh only applies to mitzvos that a person does and whose effect derive from the intention to do Hashem's will, or whose effect is the positive result of the act.  But Millah is neither.  It is done on one person by another person, and its effects are absolute, no matter what the mahul wants or thinks, as David Hamelech pointed out.  That's why Avraham Avinu saves mehulim from Gehinom, but Moshe Rabbeinu doesn't do so for people who've done the other Taryab.  So while all other mitzvos can be erased through Toheh, davka Millah can not.  And now you see why Tosfos mentioned Millah davka.

I suppose I should write Reb Elchanan's teretz better, but that will have to wait.  Anyway, I like these teirutzim more, and they also answer the other kashes I mentioned above, about changing the mitzvos to aveiros and the ease of toheh compared to the difficulty of teshuva, and Tosfos in Chulin.

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Cited text of Mesillas Yesharim

, וזה, כי לפי שורת הדין ממש, היה ראוי שהחוטא יענש מיד תיכף לחטאו בלי המתנה כלל, וגם שהעונש עצמו יהיה בחרון אף, כראוי למי שממרה פי הבורא יתברך שמו, ושלא יהיה תיקון לחטא כלל, כי הנה באמת, איך יתקן האדם את אשר עיות והחטא כבר נעשה? הרי שרצח האדם את חברו, הרי שנאף, איך יוכל לתקן הדבר הזה? היוכל להסיר המעשה העשוי מן המציאות.

אמנם, מדת הרחמים היא הנותנת הפך השלשה דברים שזכרנו: דהינו, שיתן זמן לחוטא ולא יכחד מן הארץ מיד כשחטא, ושהעונש עצמו לא יהיה עד לכלה, ושהתשובה תנתן לחוטאים בחסד גמור, שתחשב עקירת הרצון כעקירת המעשה, דהיינו, שבהיות השב מכיר את חטאו ומודה בו ומתבונן על רעתו ושב ומתחרט עליו חרטה גמורה דמעיקרא כחרטת הנדר ממש שהוא מתנחם לגמרי והיה חפץ ומשתוקק שמעולם לא היה נעשה הדבר ההוא ומצטער בלבו צער חזק על שכבר נעשה הדבר ועוזב אותו להבא ובורח ממנו, הנה עקירת הדבר מרצונו, יחשב לו כעקירת הנדר ומתכפר לו. והוא מה שאמר הכתוב (ישעיה ו): וסר עונך וחטאתך תכפר, שהעון סר ממש מהמציאות ונעקר במה שעכשיו מצטער ומתנחם על מה שהיה למפרע.

וזה חסד ודאי שאינה משורת הדין, אך על כל פנים הנה הוא חסד שאינו מכחיש הדין לגמרי, שהרי יש צד לתלות בו, שתחת הרצון שנתרצה בחטא וההנאה שנהנה ממנו בא עתה הנחמה והצער. וכן אריכות הזמן איננו ויתרון על החטא, אלא סבלנות קצת לפתוח לו פתח תקון. וכן כל שאר דרכי חסד: כענין ברא מזכה אבא (סנהדרין קד), או מקצת נפש ככל הנפש (קהלת רבה ז כז), המוזכרים בדברי החכמים, דרכי חסד הם לקבל את המעט כמרובה, אך לא מתנגדים ומכחישים ממש מדת הדין, כי כבר יש בהם טעם הגון להחשיב אותם. אך שיותרו עבירות בלא כלום או שלא ישגיח עליהם, זה היה נגד הדין לגמרי, כי כבר לא היה משפט ודין אמיתי בדברים, על כן זה אי אפשר להמצא כלל. ואם אחד מן הדרכים שזכרנו לא ימצא לחוטא להמלט, ודאי שמדת הדין לא תשוב ריקם.

For on the basis of justice alone it would be dictated that the sinner be punished immediately upon sinning, without the least delay; that the punishment itself be a wrathful one, as befits one who rebels against the word of the Creator, blessed be His Name; and that there be no correction whatsoever for the sin. For in truth, how can a man straighten what has been made crooked after the commission of the sin? If a man killed his neighbor; if he committed adultery-how can he correct this? Can he remove the accomplished fact from actuality?


It is the attribute of mercy which causes the reverse of the three things we have mentioned. That is, it provides that the sinner be given time, and not be wiped out as soon as he sins; that the punishment itself not involve utter destruction; and that the gift of repentance be given to sinners with absolute lovingkindness, so that the rooting out of the will which prompted the deed be considered a rooting out of the deed itself. That is, when he who is repenting recognizes his sin, and admits it, and reflects upon his evil, and repents, and wishes that the sin had never been committed, as he would wish that a certain vow had never been made, in which case there is complete regret, and he desires and yearns that the deed had never been done, and suffers great anguish in his heart because of its already having been done, and departs from it for the future, and flees from it then the uprooting of the act from his will is accredited to him as the uprooting of a vow, and he gains atonement. As Scripture states (Isaiah 6:7), "Your wrong will depart, and your sin will be forgiven." The wrong actually departs from existence and is uprooted because of his suffering for and regretting now what had taken place in the past. 


This is certainly a function of lovingkindness and not of justice. In any event, however, it is a type of lovingkindness which does not entirely negate the attribute of justice. It can be seen as according with justice in that in place of the act of will from which the sin arose and the pleasure that it afforded, there is now regret and suffering. So, too, the time extension constitutes not a pardoning of the sin, but rather God's bearing with the sinner for a while to open the door of repentance to him.