Our Gemara on amud aleph discusses a case where one stated the claim that a thief stole the deposit and took an oath and then witnesses came and testified that he had taken it, and he returned and again stated the claim that a thief stole the same deposit and again took an oath and then witnesses came and again testified that he had taken it. More notably, Rambam (Hilchos Geneiva, 4:5) rules that even if this occurred 100 times, if he makes the oath and then is discredited by witnesses, he will have to pay double for each oath made.
Chashukei Chemed suggests this case as a possible proof to the ruling that even if one has been shown to lie several times, if he has demonstrated appropriate and credible repentance, that might be believed once again. Otherwise, how would the judges of the court allow this man to repeatedly make this oath when he is a proven liar.
What are we to make of someone who repeatedly repents, breaks our trust, and then repeats it again? A sinner who repeatedly sins, and then repents?
The Gemara Yoma (85b) warns:
One who says, “I will sin and then I will repent, I will sin and I will repent”, Heaven does not provide him the opportunity to repent.
The Gemara 87a notes the repetition, and therefore states that it specifically means repetition, because with the repetition, I would say through habit and rationalization, “it becomes to him as though it were permitted to him”, and therefore more difficult to repent.
Many commentaries understand that this is not an absolute refusal to accept his teshuva, it just requires extra effort and mindfulness to overcome the loss of sincerity (see Likute Amarim Tanya (25:4). He also says in (Iggeres HaTeshuva 11:1) that this rule only applies if he has the ability to resist the temptation but nonetheless decides to “put it on the tab”, and figure, “I’ll buy now, repent later.” Bas Ayin (Derushim Leshabbos Teshuva Shabbos 4) offers a clever analysis. It is difficult to do teshuva on the sin because he must first repent on the sin of abusing God’s patience and kindness, that is he must repent for thinking he could get away with sinning and repenting. After that repentence, his repentence for the actual sin can now be accepted.
This is not a perfect comparison to our case, as we do not know the state of mind of the person who made the false oath, repented, and falsely swore again. However, we can say, it should not be no worse than the person who cynically decided to sin and repent later. The person in our example, might have said that, or might have been fooling himself and genuinely meant to repent.
There is a fascinating Rambam which caused many commentaries to stretch to fit various answers, but I believe can be explained by understanding something I discovered about the Rambam’s approach, leshitaso, when it comes to an attitude of sin.
The Rambam (Laws of Teshuva 4:1) seemingly codifies this halacha, but neglects to add the repetition clause. He states a number of examples where God will not grant the person assistance in repenting, including: “One who says, I will sin and then repent." Included in this category is one who says: "I will sin and Yom Kippur will atone [for me]."
The Lechem Mishna and other commentaries wonder why the Rambam doesn’t include the repetition, even though it is very clear from the context and discussion of the Gemara it is referring specifically to a repeat offender. Some offer the answer that Rambam is basing his ruling on a different beraisa, which does not have the repetition.
This is similar to another Rambam found in Hilchos Deos (2:3) which states: “Whoever gets into a rage is considered as if he committed idolatry.” Over there as well, the commentaries ask that the Rambam diverges from the Gemara (Shabbos 105b), which states “One who destroys his vessels in a rage is as if he is committing idolatry.” The Gemara requires more specific action, and instead the Rambam codifies it as a mode of thought without action.
Various answers and distinctions are given. However, I believe the answer to both of these apparent divergences between the Gemara and the Rambam’s codification is that according to the Rambam it is not about the sin alone, but about the state of the mind and soul. According to the Rambam the human intellect is the link from God to Man. The greater the person elevates his thinking, and his modes of thought and resultant behavior, the more his intellect becomes in harmony and resonates with God. This is a divine pipeline between God and man. (To understand more about this Maimonidean philosophy, study the poetically sweeping and climactic chapter of the Moreh Nevuchim III:51. Also see what I wrote on my blog Psychology of the Daf, Bava Kamma 104.) Therefore, Rambam interpreted both cases not as actually breaking something, nor sinning repeatedly. Instead, he interprets the Gemara to be discussing a state of mind which predisposes one to repeated sin, and a state of mind where rage is so strong that somebody is out of control and could break vessels. It’s not about the action. It’s about the state of mind that has become animalistic, and no longer connected to God. And I believe you can see this reflected in the Rambam’s words, “I will sin and recant is in the same category as somebody who says I will sin, and Yom Kippur will attain forgiveness.” Because, to the Rambam’s thinking, it is all the same. It is reflective of an inner attitude of disregard and being given over to sin, a sign of an inner state. It is a symptom, not the disease. The disease is the loss of intellectual spiritual capacities, that is rational and God – focused mentality.
Regardless, Teshuva is always possible. But that is between God and Man. There are certain personalities that are so distorted, that it is foolhardy to trust, as sincere as they may sound. For example, persons in the throes of addictions, will say and do anything to get away from the pain of the moment. Also, some, (but not all,) kinds of sexual predators may feel true remorse but still be under strong compulsions that are not easily redirected. In the past, certain rabbinic authorities were found to have erroneously turn a blind eye or even participated in covering up crimes because of a well meaning belief that the person did teshuva. I believe misapplication of halakhic technical thinking and misguided halakhic rationales, such as the concept of accepting the Baal Teshuva have been incorrectly applied to dangerous and unmanageable compulsive behavior. We have come to understand that sexual abuse is not merely a moral lapse, but rather comes from more complex psychological dynamics that cannot be remediated by remorse alone.
Teshuvah is fine for God but it doesn’t necessarily make the potential offender safe.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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