Our Gemara on Amud Beis discusses an incident where Rabban Gamliel blinded the eye of his Canaanite slave Tavi, and he experienced great joy as a result. Rabban Gamliel always wanted to free Tavi, because he was considered an extraordinarily learned and pious individual (see Mishna Succah 2:1, Mishna Berachos 2:7.) Yet, it is generally prohibited to emancipate a Canaanite slave, as discussed in Gittin (38b). The injury provided a perfect opportunity for Rabban Gamliel to free his slave, as blinding the eye of one’s slave results in his emancipation (see Exodus 21:27).
However, assuming it is forbidden to free a slave, is it really acceptable to then be joyous? A commandment is the opportunity to perform in accordance with the will of God, if we unable to do so, we should appear despondent, not pleased, even if Tavi was a special case and deserving to be free. As the Gemara in Avodah Zara (3b) rhetorically declares in regard to those who were happy to leave the Succah: “Granted that one is exempt from performing the mitzva and is permitted to leave his Succah, but should one kick it?”
A possible answer is that the prohibition of freeing a slave is not absolute, as we find Rabbi Eliezer freed his slave in order that he become a full Jew so that he could be the tenth man for his minyan. The Gemara (Gittin ibid) records a dispute and not all hold that this is a commandment, so perhaps Rabbi Gamliel followed that position. Ritva (Megillah 28a) holds that the prohibition, though based on a verse, is rabbinic. If so, that also indicates an idea that if one becomes exempt from a rabbinic commandment, it is not considered disrespectful to seem pleased about it. Other Rishonim hold the prohibition is De’oraysa, with certain built in leniencies (Chinuch 347.)
However, this may also involve a more nuanced idea about how to relate to the commandments and individual experiences. One might argue that since Tavi was an exception, and would make good use of his freedom to accomplish mitzvos, Rabban Gamliel did not feel it was improper to be happy about his freedom. This is not considered disrespectful as Rabban Gamliel supported the ethos of the commandment; he just didn’t believe it applied to Tavi. He could not use such reasoning to deliberately usurp the law, but if somehow Tavi becomes free, it can be seen as a good thing. If this idea is correct, it gives us another reason to speculate about reasons for the commandments. The Gemara Sanhedrin (21a) records a dispute between Rabbi Shimon and Rabbi Yehuda, whether the apparent reason for a commandment can influence the application of the halakha; and we rule in accordance with Rabbi Yehuda, that presumed reasons do not influence the halakha. But, even according to Rabbi Yehuda, it might still affect how you are supposed to feel when you are unable to fulfill the commandment.
This raises another question: Why is this not considered heretical to believe that a divine and perfect Torah does not apply to all situations. The Rambam provides us a framework and answer. He says Torah is com[pared to other matters in nature, which can be generally good and reflect divine wisdom, but in specific situations, be quite the opposite. For example, we can all agree that “Gravity” is a vital force in the world, and praise God for his wondrous works. At the same time, none of us would be pleased about gravity when falling from a balcony.
In the Guide for the Perplexed (III:34), Rambam explains that the commandments are generally for one of three purposes: To promote physical health, spiritual health, or the smooth running of society. But just as the general welfare and survival is provided by natural processes, yet individuals may have diseases or defects that nature does not protect them from, so too the Torah is designed to help the majority. There may be times, or individuals, that suffer and are hurt by a particular Torah requirement. Caution is required here in understanding Rambam’s idea. He is not advocating that an individual customize his Torah obligations even if he could verify with absolute certainty that this aspect of the Torah holds him back from experiencing “shleimus”. This person must still follow the laws. This is similar to civil law: One is not exempt from obeying the law that is designed to promote the greatest good and common welfare, even if he can offer a strong argument why it does not promote his personal welfare. The Torah is still a legal system aside from a spiritual system. So even though Rambam states firmly that it is indeed possible for a Torah requirement to be in some way unhelpful and even destructive to an individual at a certain point in time or in life, the legal obligations remain unchanged. (For more discussion about the Torah as both a legal system and religious system, see our Blogpost Psychology of the Daf, Bava Kama 71 https://nefesh.org/SimchaFeuerman/punishment-or-consequence-bava-kamma--psychology-of-the-daf-yomi.html )
Rabban Gamliel had no problem with feeling that the Torah law preventing him from freeing his slave was not good for Tavi, as he may have held like the Rambam. The Rambam holds that there is no guarantee that a Torah rule that is generally positive has to be good for every individual at every time. This does not lessen the requirement to obey, but if circumstances caused an objection, it does not require any regrets.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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