The theme of Simcha recurs throughout Parshat Re’eh. The notion of Simcha is first introduced regarding Korbanot, which must be eaten in Yerushalayim with one’s family in a festive manner. Similarly, Parshat Re’eh delivers the commandment of Maaser Sheini, which must also be eaten BeSimcha in Yerushalayim. The Parsha concludes with the Chiyuv to rejoice on the Shalosh Regalim.
Rav Soloveitchik points out that there is a connection between Simcha and being “Lifnei Hashem,” in the presence of Hashem. The Chiyuv of Simcha is triggered when one is in the presence of HaKadosh Baruch Hu. Thus, there is an obligation of Simcha on the Shalosh Regalim and when bringing Korbanot and Maaser Sheini, because all three take place in Yerushalayim, in presence of Hashem. However, Simcha does not only stem from being in close physical proximity to the Shechinah; the Chiyuv of Simcha also exists when we are spiritually close to Hashem. For example, because we are spiritually close to Hashem on Rosh Hashanah and Yom Kippur, there is an element of Simcha on those days, as well (as the Rambam states in Hilchot Chanukah).
Although Halacha indicates that the degree of Simcha required is equivalent on all of the Regalim, this does not seem to be true from the Pesukim. The Torah does not even explicitly mention an aspect of Simcha on Pesach, and mentions the word Simcha only once regarding Shavuot. On Sukkot, however, we are emphatically commanded to rejoice, a point highlighted by the words “VeHayita Ach Sameiach,” “and you shall be exceedingly happy” (16:15). In addition, in Parshat Emor, the Torah again commands us to rejoice on Sukkot. Why is it that Sukkot seems to have a greater degree of Simcha than the other Regalim?
Rav Zvi Sobolofsky answers this question based on the Rav’s connection of Simcha to being Lifnei Hashem. As mentioned above, the Yamim Noraim bring us spiritually closer to Hashem. In fact, the Rambam writes (in the seventh chapter of Hilchot Teshuva) that before performing Teshuvah on the Yamim Noraim, we are extremely distant from Hashem. Once we perform Teshuvah, however, Hashem is directly in our presence. Because we are so close to Him after the Yamim Noraim, and being close to Hashem triggers the Chiyuv of Simcha, the holiday of Sukkot, which immediately follows the Yamim Noraim, carries a stronger level of Simcha.
May we all merit to achieve Teshuvah, thereby drawing ourselves spiritually closer to Hashem, and to become close to Him in a physical sense as well with the rebuilding of the Beit HaMikdash BiMeheirah BeYameinu.