The Mishnah at end of Yoma teaches that one who says: "I will transgress, and then I will repent; I will transgress, and then I will repent" is not afforded by Heaven the opportunity to repent.
The Gemara asks why one has to say this twice and as an answer the following saying of R. Huna is cited: R. 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 explains: Since he transgressed twice, he is not afforded by Heaven the opportunity to repent, because the prohibition seems to him as if it were permitted.
This is difficult to understand, because if one actively transgresses, what difference does it make if he said that he will repent of if he did not say he would repent? 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?
It appears to our master that despite the words of Rashi that the Gemara understood the Mishna to mean what it appears to be saying that one who transgresses a prohibition twice with the intention of repenting is only then 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 has to make the statement only once. The Gemara therefore asks why it is necessary to say twice that one will transgress and repent before he is denied the opportunity to repent.
But in truth there is a big 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, but only if one resolves to repent and to sincerely regret 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, because he knows 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, inasmuch as by doing so would prevent him from subsequently repenting of the transgression. Instead, he will transgress and will then 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 having been nullified by his 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 him the opportunity to repent the first time, since if he repents, he will transgress again. But if he is unable to repent for the first transgression, he will be saved from the subsequent transgressions.
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. And this clear in the words of the Gemara.
The same Mishnah teaches that if one who says: "I will transgress and Yom Kippur will atone," then Yom Kippur does not atone for him.
The Gemara raises the question whether this Mishnah conflicts with the opinion of Rebi who holds that Yom Kippur atones both for those who repent and for those who do not repent. But the Gemara concludes that the Mishnah need not conflict with the opinion of Rebi, because "reliance is different." Rashi explains that if one actually commits a transgression in the expectation that Yom Kippur will atone, Yom Kippur does not atone in that case.
Now a scholar once asked our master why the Gemara did not use this reasoning in the tractate of Shavuot (13) to answer the question how, according to Rebi, it one could ever be subject to the punishment of כרת for eating on Yom Kippur. The Gemara in Shavuot is hard pressed to find an answer, but why did it not answer simply that, even according to Rebi, one could be subject to כרת for eating on Yom Kippur in the expectation that Yom Kippur would atone for the transgression? And our master answered correctly that the question is not compelling. For if we said that only one who ate on Yom Kippur in the expectation that Yom Kippur would atone for the transgression, then there would have been no point in mentioning that the punishment for eating on Yom Kippur is כרת. Instead, the Scripture should have mentioned only the positive commandment to fast (וְעִנִּיתֶם אֶת נַפְשֹׁתֵיכֶם). And if the individual would not be aware of the punishment of כרת, he would not come to the point of saying "I will transgress and Yom Kippur will atone for the כרת," since he would be unaware that eating on Yom Kippur subjected him to a penalty for which he required atonement. Thus, if the individual did eat on Yom Kippur, he would not be subject to the penalty of כרת, because Yom Kippur would indeed atone for his transgression. But it is surely impossible to say that the Scripture mentioned the penalty of כרת for eating on Yom Kippur for no other purpose than to impose it upon one who eats on Yom Kippur with the expectation that Yom Kippur would atone.
In the Mishnah at the end of Yoma, R. Akiva says, "how fortunate are
you, oh, Israel. Before whom are you being purified? Who is purifying
you? Your Father in Heaven, as it is written, 'and I will pour pure
water upon you, and you will become pure. From all your contaminations
and from all your abominations I will purify
(וְזָרַקְתִּי עֲלֵיכֶם מַיִם טְהוֹרִים וּטְהַרְתֶּם מִכֹּל טֻמְאוֹתֵיכֶם וּמִכָּל גִּלּוּלֵיכֶם אֲטַהֵר אֶתְכֶם).'"
Behold R. Akiva, after the Temple was destroyed and the Sanctuary of the Eternal was burnt, sought to comfort Israel for the loss of the Yom ha-Kippurim service which brought atonement through the sin-offering (פַּר הַחַטָּאת) and the two goats (שְׁנֵי הַשְּׂעִירִם).
Behold there are two forces that upset our souls and, like a serpent, wait along the way of the Eternal to cause us to do evil. First, desire, the first sin, which leads us astray to do evil. Second, sustenance for our lives, the burden of which is too heavy to bear and forces us to depart from the way of the Eternal. Now when Israel dwelled upon its land, the Holy Land, upon which the eyes of the Eternal are always set, the desire to sin was not aroused to the highest degree. Nor did the evil inclination exercise complete control over the Children of Israel to push them away from the Eternal, because they dwelled in a place consecrated to the Eternal. Moreover, "the atmosphere of the land makes one wise" (ואוירא דארעא מחכים) and "the beginning of wisdom is the fear of the Eternal" (רֵאשִׁית חָכְמָה, יִרְאַת ה׳). They also found it possible to support themselves more than adequately without excessive effort and toil, because they dwelt securely in peace, each man under his vine and fig tree. But in that ideal situation, any transgression, any departure from the way of the Eternal to stand on the path of evil, was very grave. It was therefore essential for them to perform on the Fast Day both the sin-offering (חטאת) and the guilt offering (אשם) to atone for their guilt, which was great.
However, when the Children of Israel left their land and were exiled to foreign lands, the evil inclination arose like an adversary to push them off the way of the Eternal, because outside Israel his strength is mighty and from his grasp none can be saved. As the Sages said, "whoever lives outside Israel is like one with no G-d." Also their livelihood provided them only with bitter herbs, for they had to devote their whole lives to earn their bread. And it became very difficult for them to observe the commandments of the Eternal. So for a loaf of bread a man would sin against G-d and desecrate the Sabbath and His festivals and would bear false witness against his friend. For who could bear the shame of hunger and poverty? But for just that reason, their sins were not too great to be forgiven, and the Eternal, in His goodness, would forgive them when they returned to Him. But if we have neither Priest nor altar to provide atonement, upon whom can we rely? On our Father in Heaven Who acts toward us with kindness and truth.
This is what R. Akiva meant when he said "how fortunate are you, Oh, Israel." Even though our city is desolate and our Temple destroyed, we still have upon Whom to rely -- upon our Father in Heaven. In other words, there is an atonement for our sins in that the Restorer of our souls is now far away from us and has ascended to Heaven and does not pour His spirit upon us -- "the blessings of Heaven above" (בִּרְכֹת שָׁמַיִם מֵעָל), by which we could understand and become wise and avoid sin. Nor do we have the temporal blessings below, "the blessings of the deep that coucheth beneath" (בִּרְכֹת תְּהוֹם רֹבֶצֶת תָּחַת), because all we have left but is our bodies, and we eat bread only through the sweat of our brow. But this withdrawal of the blessings, in itself, is an excellent excuse for us, through which our sins are forgiven as if through the service of Yom ha-Kippurim. And to reinforce his words, R. Akiva quotes the words of the prophet Yehezkeil who, referring to the bitter days of exile, said "And I will pour pure waters upon you, and you will be purified. From all your contaminations and all your abominations I will purify you." For the difference between contamination (טומאה) and abomination (גלל) is that contamination is invisible whereas an abomination is a disgusting thing that is visible. These two words suggest the two types of transgressions mentioned above. One who defiles his soul by eating food unfit to be consumed or by having illicit relations is considered revolting in his person and his soul as Tosaphot write in Hulin that it is exceedingly disgraceful to eat something that is forbidden, because it disfigures his person. Thus, our Sages say that an animal that was fed forbidden foodstuffs is considered blemished and is unfit to be brought as a sacrifice. Such transgressions are therefore represented by the word "גלל." But those transgressions that, like the desecration of the Sabbath or swearing falsely that are committed because of financial pressure, have an advantage over the former class of transgressions in not defiling the person of the transgressor. And the second group of transgressions are represented by the word "טומאה" which suggests that these transgressions have a less conspicuous physical effect. The words "and I will pour pure water upon you" suggest that water will be poured from afar, from a high place, "for I am in Heaven and you are in the land of your enemies. And this itself is an excuse for you and therefore you will be purified of all your impurities and from all your abominations."
And R. Akiva mentions another advantage of the exile that did not exist at the time of the Temple. "And it says again, 'the hope (מִקְוֵה) of Israel, the Eternal, will save you in a time of peril,' just as the ritual bath (מִקְוֵה) cleanses the unclean, so does the Holy One Blessed Be He cleanse Israel." For the very fact that we have no one upon whom to depend except our Heavenly Father will create the proper spirit within us and will direct our hearts toward Him to serve Him, and all the while Israel will look upward and subjugate their hearts to Heaven. Now the purification of the ritual bath occurs when a person immerses himself completely beneath the water and is completely separated from anything else. So, too, Israel, when they have no one upon whom to rely and no one to support them, and they just look toward G-d for mercy, then will they be purified and their souls will be cleansed more than by the guilt offering or the Scapegoat. For the Merciful One desires the heart. And this is how the verse "Israel is saved by the Eternal, an everlasting salvation." "Everlasting salvation" salvation means that we may be saved in every generation even when Mount Zion is desolate without worshipers to bring sacrifices their. In such times, Israel is saved by the Eternal, and it is an everlasting salvation. That is what is meant by "the hope of Israel is G-d" (מִקְוֵה יִשְׂרָאֵל ה'). Just as a ritual bath cleanses when one immerses his entire body and is completely surrounded by water, so the Holy One Blessed Be He cleanses Israel when they look heavenward and their eyes are focused only on Him.