Our Gemara on Amud Beis considers the moral and halakhic dilemma of what to do if by violating a minor prohibition, one can accomplish a great merit. Our Gemara discusses the case of an animal found in Yerushalayim, which is assumed to have been dedicated for a sacrifice. Since it is of unknown designation, it cannot be brought as is on the altar, as each sacrifice has different procedures. Redeeming a non-blemished animal is forbidden, but the transaction would be binding. Thus, one might think he could redeem this animal in order to include the money in the purchase of a variety of sacrifices that it might have been, so as to accomplish its original purpose. Even though this would be a great merit to the original owner who has lost his animal, Rabbi Yochanan rules that it is not permitted to commit even a minor violation for the large merit of another.
However, this would seem to contradict a different Gemara (Eiruvin 32b), where Rabbi Yehuda Hanasi states that it is preferable for a sage to commit a minor sin of tithing on non-adjacent produce in order to protect a less observant Am Haaretz, who will buy the produce, and possibly neglect to tithe.
Rashba (Shabbos 4a, and Tosafos Eiruvin 32b) quotes Rabbenu Tam who draws a distinction between the case in Eiruvin and the case in our Gemara. In our Gemara, the person who found the animal had no hand in the mishap, therefore he has no obligation to even commit a minor sin to forestall the other person’s loss. However, in the case of Eiruvin, since the produce originally belonged to the sage, he has more of an obligation to prevent the sin of the Am Haaretz and should tithe even from non-adjacent produce.
Yismach Moshe (Ki Tisa 3) uses this principle to explain Yaakov’s behavior in running away from Esau, via a complex halakhic and moral calculus. He first discusses the halakhic dispute between Rambam and Rabbenu Yerucham as to whether one can voluntarily martyr himself instead of violating a prohibition, even if it is not one of the three sins of idolatry, sexual immorality, and murder. Rambam rules one is not allowed, while Rabbenu Yerucham permits it. He also concludes that an exceedingly pious person is expected to martyr himself even so as not to violate a positive commandment (See Shulkhan Arukh YD 157:1, Rama, and Shach 157:1). Based on this assumption, Yismach Moshe wonders how Yaakov could have abrogated his obligation to honor his parents by running away, even if his life was in danger. A tzaddik of Yaakov’s proportion should have been willing to risk martyrdom in order to not lose out on even a single mitzvah, let alone a major one such as honoring parents.
Yismach Moshe’s answer is that since Yaakov had a hand in Esau’s murderous rage, he also was obligated to commit a relatively minor violation instead of the possibility of Esau committing murder.
This is a clever use of the principles we discussed, but one must wonder why Yismach Moshe didn’t utilize a simpler and more logical argument: If Yaakov would give up his life, ironically to fulfill the mitzvah of honoring his parents, how would this ultimately be his parents’ will? Would they rather a dead son, who might have been able to have a bit more time to honor them, or a live son living safely far away?
The answer to this lies in the depth of legalisms in halakhic and ethical thinking. Do we allow obvious moral considerations to enter into our evaluation of the strict letter of the law? For example, technically Yaakov was obligated in the mitzvah of honoring parents no different than any other mitzvah, such as shaking a Lulav (Assuming the Avos kept the Torah, see Yoma 28b). If so, would he be allowed to reason that paradoxically if he stayed around to fulfill honoring his parents, they would suffer more grief from his death? Or, is that irrelevant to his personal obligation to fulfill the mitzvah? While this thinking seems overly legalistic and counterintuitive, halakha is, in fact, legal, and law is about compliance as much as the spirit of the law.
There is a similar example regarding a tragic Talmudic story of Rabbi Rechumi and his wife (Kesuvos 62b):
כִּי הָא דְּרַב רְחוּמִי הֲוָה שְׁכִיחַ קַמֵּיהּ דְּרָבָא בְּמָחוֹזָא, הֲוָה רְגִיל דַּהֲוָה אָתֵי לְבֵיתֵיהּ כֹּל מַעֲלֵי יוֹמָא דְכִיפּוּרֵי. יוֹמָא חַד מְשַׁכְתֵּיהּ שְׁמַעְתָּא. הֲוָה מְסַכְּיָא דְּבֵיתְהוּ: הַשְׁתָּא אָתֵי, הַשְׁתָּא אָתֵי. לָא אֲתָא. חֲלַשׁ דַּעְתַּהּ, אַחִית דִּמְעֲתָא מֵעֵינַהּ. הֲוָה יָתֵיב בְּאִיגָּרָא, אִפְּחִית אִיגָּרָא מִתּוּתֵיהּ וְנָח נַפְשֵׁיהּ.
This is as it is related about Rav Reḥumi, who would commonly study before Rava in Meḥoza: He was accustomed to come back to his home every year on the eve of Yom Kippur. One day he was particularly engrossed in the halakha he was studying, and so he remained in the study hall and did not go home. His wife was expecting him that day and continually said to herself: Now he is coming, now he is coming. But in the end, he did not come. She was distressed by this, and a tear fell from her eye. At that exact moment, Rav Reḥumi was sitting on the roof. The roof collapsed under him, and he died. This teaches how much one must be careful, as he was punished severely for causing anguish to his wife, even inadvertently.
The ironic and obvious question here is how did this punishment vindicate Rav Rechumi’s wife? Not only did she have no husband for this Yom Kippur, but she now also became a widow? We must consider that despite the illogic of this, Rav Rechumi was punished for the sin of neglecting his wife, and that sin was independent of her own wishes though obviously related in a moral sense.
To understand Torah, one must appreciate that it operates on two levels. There is the law, which is about rules, and then the deeper meanings, purposes, and intentions. Though arguably the most important part of the Torah is the intention and spiritual content, the law is still the law.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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