האומר אחטא ואשוב אחטא ואשוב אין מספיקין בידו לעשות תשובה
If one says I will transgress, and then repent; I will transgress and then repent,” Heaven does not afford him the opportunity to repent.
The Gemara (Yoma 87a) asks why one has to repeat the statement that he will transgress a prohibition in order to be denied the opportunity to repent, and the following saying of R. Huna is cited:
Rav Huna said in the name of Rav whoever transgresses a prohibition and repeats the transgression a second time comes to consider the prohibition as if it were permitted.
Rashi comments: Since he has transgressed twice, he is not afforded by Heaven the opportunity to repent, because what is prohibited seems to him as if it were permitted.
This is beyond understanding, because if one actively transgresses, what difference does it make if he said that he will repent of the transgression, or if he did not say he will repent of the transgression? Either way, the prohibition now appears to him as if it were permitted. Moreover, what is meant by the phrase “he is not afforded by Heaven the opportunity to repent”? If the prohibition appears to him as if it were permitted, he would not repent regardless of whether Heaven affords him the opportunity?
Our master explains that, contrary to the words of Rashi, the Gemara understood the Mishna to mean what it appears to be saying that it is only the one who transgresses a prohibition twice with the intention of repenting that is not afforded the opportunity to repent. And the Gemara’s question was how is this different from the statement of another Mishnah that if one says that he will transgress and Yom Kippur will atone, Yom Kippur does not atone for his transgression? Thus, with regard to Yom Kippur, one must make the statement only once. The Gemara therefore asks why it is necessary to repeat that one will transgress and repent before being denied the opportunity to repent.
But in truth there is a great difference between the two cases, inasmuch as Yom Kippur comes automatically. For if we say that one who relies on Yom Kippur to atone for his transgression receives atonement for the first such transgression, then the strap would be untied, and everyone would do what he wants with this assurance of atonement. However, if one transgresses with the intention of repenting, repentance still does not come automatically; it comes only if one resolves to repent and sincerely regrets his transgression. And who knows if he will in fact repent? Therefore, not everyone will dare to sin with the intention of repenting afterwards. But in that case, what is the difference between a person who transgresses one time with the intention of repenting and a person who does so many times? And why is the latter not afforded the opportunity to repent?
The Gemara therefore concludes that the Mishnah was speaking about one who wishes to perpetrate a deception, knowing that by committing a transgression twice he would view the prohibition as if it were permitted and would not repent of such a transgression. Therefore, he cleverly says that he will not transgress twice consecutively without repenting in the interim, because to do so would prevent him from repenting of the transgression. Instead, he will transgress, intending to repent immediately, so that it will be as if he had not transgressed. Only then will he transgress, and it will not appear to him as if the prohibition is permitted, because he will not have transgressed the prohibition twice consecutively, the first transgression having been nullified by his immediate repentance. Then, after the second transgression, he will repent once again, so that he may transgress yet again.
The Mishnah teaches that Heaven does not afford such a person the opportunity to repent the first time, because his planned repentance is intended to enable him to transgress later. But if he is unable to repent for the first transgression, he may be saved from the subsequent transgressions, because, his scheme having been thwarted, he will not feel safe in transgressing a second time.
This is the answer of the Gemara citing the dictum of R. Huna in the name of Rav that one who transgresses a prohibition twice considers the prohibition as if it were permitted. In other words, the Mishnah, contrary to the initial assumption, is not referring to one who transgressed two times with the intention of repenting. Rather, it is referring to one who wishes to circumvent the dictum of R. Huna, so that the prohibition that he intends to transgress should not come to seem to him to be permissible after the second transgression. He therefore says in advance that I will transgress and then I will repent and then I will transgress and then I will repent. Only in that case is he not afforded the opportunity to repent for the first transgression. This clear in the words of the Gemara. (שביבי אש)