The most obvious connection between Tisha b’Av and parshat Vaetchanan—which is always read on the Shabbat following this saddest of days—lies in the opening lines of the parsha, where Moshe pleads to enter the land from which his beloved people would be exiled hundreds of years later.  

The origins of Tisha B’Av stem from the chet hameraglim, the sin of the spies, in which the Jewish people lacked the desire to enter the land. Upon hearing the report of the spies—on the 9th day of Av—the Jewish people cried out, causing G-d to exclaim, “You cried a needless cry; I will establish for you [a reason to] a cry for all generations” (Taanit 29a). And it is that error with which Moshe opens up sefer Devarim—always read the Shabbat before Tisha b’Av—as the Jewish people are once again on the verge of entry into the Land. How tragic when those who are able to attain a gift do not want it, and those who desire that same gift are unable to attain it!  

The connection between Vaetchanan and Tisha b’Av is further highlighted by the fact that the Torah reading chosen by our Sages for Tisha b’Av comes from this parsha. “When you bear children and grandchildren and will have been long in the land, you will grow corrupt…” (Devarim 4:24)  

Yet I would argue that the most important connection between Tisha b’Av and the parsha lies in the verse, “You shall do, hayashar vehatov, what is straight and good in the eyes of G-d, so that it will be good for you; and you will come and inherit the good land that G-d has promised you” (Devarim 6:18). It is this verse which serves as the obligation to act lifnim meshurat hadin, a concept that does not lend itself easily to translation, but incorporates the idea of acting beyond the letter of the law and incorporating the spirit of the law. The Biblical verse itself links the practice of going beyond the law to the inheritance of the land. It is thus no surprise, then, that Rav Yochanan claims that, “Jerusalem was only destroyed… because people insisted on the strict application of the law and did not practice lifnim meshurat hadin” (Baba Metziah 30b). 

As the Ramban explains, the Torah could not possibly legislate all human interaction. The Torah makes mention of a number of various prohibitions, such as slander, revenge, passivity in the face of wrongdoing, and cursing others, as well as obligations such as respecting elders, giving charity, and displaying sensitivity to strangers, and follows up with a general rule to go beyond just what the Torah says. The Ramban notes as an example that of the law of bar metzra, where one who is selling land is obligated to give the right of first refusal to his neighbour - at that same price. The Torah does not allow one to take advantage of the fact that one would generally pay a premium for an abutting property.  

This echoes a similar sentiment expressed by the Ramban on the obligation “to be holy” (Vayikra 19:2), where the Ramban notes that one can follow every technical detail of the Torah and yet still be a scoundrel. Whereas being holy relates to our relation to G-d, the mitzva to do "the straight and the good", refers to our interpersonal relations. 

Law alone does not make one a better person, and no law can ensure basic human decency in each and every situation. The most important “laws” are the ones not directly mentioned. The Talmud (Yoma 86a)—in commenting on another verse from the week’s parsha, “to love the Lord your G-d with all your heart,” (Devarim 6:4)—envisions the tragic situation where one studies Torah, honours Torah scholars and yet is dishonest in his business dealings and does not act with kindness towards others. The “Torah” of this person, the Talmud declares, is actually a desecration of the name of G-d. Better that such people would not involve themselves in Torah study or observance, lest a link be made between ritual observance and unethical conduct.  

We live in a society in which people often fight for their strict legal rights. The word lifnim means “before”, indicating the Torah’s desire that we resolve our differences before the shurat din, before we must appear in court, where “the straightness of the law” must be applied, come what may. Only before we get to court can mitigating circumstances play the important role they should. Once we arrive in court, it is strict justice that must apply, notwithstanding the harm that may cause in any given case.  

At times, sadly, we may have no choice but to go to court. And Jewish law has many laws pertaining to our justice system. Even before Moshe makes mention of the sin of the spies, he reminds the people of the importance of appointing proper judges. Ideally, we would like our judges to have little to judge, but much time to devote to the study and teaching of Torah. If we would only understand the overarching importance of lifnim meshura hadin, we would act in such a way that disputes might be avoided rather than adjudicated.