Rashi interprets the metaphor of a strong-boned donkey and the reference to the land as alluding to Yissachar’s relationship with the Torah. Yaakov Avinu points out Yissachar’s spiritual role as bearer of the yoke of Torah and cultivator of the spiritual treasures of our people. Why does the blessing include “his seeing tranquility and it was good”? The significance of the blessing is Yissachar’s relentless commitment to bearing the yoke of Torah, even if it might be a challenging task at times. His ability to rest while standing up, without having to remove his parcels, demonstrates that regardless of the prevailing conditions, Yissachar can be relied upon to study and uphold the Torah. How do tranquility and its benefits relate to the remainder of the blessing?
Horav Matisyahu Solomon, Shlita, quotes Horav Leib Friedman, zl, who heard from one of Yerushalayim’s preeminent tzaddikim (there were many) that the Torah is teaching us the barometer for measuring oneself with regard to his absolute commitment and devotion to avodas Hashem, serving the Almighty. He should question himself: How much am I willing to relinquish to fulfill the ratzon, will, of Hashem? For example, both Kayin and Hevel offered sacrifices to Hashem. The difference was that Hevel offered his finest, his firstborn cattle and sheep. He understood that one gives to Hashem what he normally would want for himself. In fact, he wants to give up the best for Hashem. The Almighty does not play second fiddle to anything or anyone. Only the very best should be for Him. This attitude indicates one’s level of clinging to Hashem. Likewise, in our mundane world everyone wants to rest (not necessarily a vacation, cruise, etc. just to relax in a calm, restful, peaceful setting). When he achieves this goal, finds the opportunity and place for this menuchah, rest, what does he do about it? Yissachar honors Hashem with it. Sure, he, too, would like to throw up his feet and rest without a care in the world. Hashem, however, comes first. This becomes a place in which he can devote himself totally without any disturbance to one thing: to study Torah. Yissachar gives it all to Hashem; even his vacation becomes an opportunity to serve Hashem with greater calm.
Rav Leib added that, upon hearing this pshat, exposition, the Chazon Ish, zl, was pleased to the extent that, two months later, he made a point to tell it over, with great excitement and admiration. Veritably, it makes sense that one should give his “best” to Hashem, but not everything that makes “sense” takes first place in our minds.
Horav Gedalyah Schor, zl, commented that the letters mem and samech (of the Hebrew alphabet) miraculously remained in position on the Luchos, Tablets. (The letters engraved on the Luchos penetrated the entire thickness of the Luchos. Consequently, the middle sections enclosed by the letters samech and mem sofis [final mem] were completely unattached to the body of the Luchos. These middle pieces remained in place by means of a miracle.) Therefore, regarding the tribe of Yissachar, this miracle was alluded to: Vayehi l’mas oveid, mas equals mem samech. Indeed, talmidei chachamim, Torah scholars who devote their entire lives to the study of Torah, who have very little to no outside sustenance, who live on little food and less sleep, should, by all rules of nature, not survive. They do, because Hashem miraculously provides for them. They devote themselves to spiritual ascendency. Thus, they are sustained spiritually.
A rabbinic conference was convened in Vilna to address the difficult challenges confronting the yeshivos during the depression years, when funds from America were coming sporadically to Europe. During one of the keynote sessions, a distinguished askan, communal leader, declared that in view of the material deprivation to which the yeshivos were subjected, it was unrealistic that they would be able to keep their doors open. Chas v’shalom, Heaven forbid, the yeshivos would be forced to close down. When the gadol ha’dor, pre-eminent leader of the generation, Horav Chaim Ozer Grodzenski, zl, heard this, he immediately stood up and, with a raised voice, declared, “The Torah attests the ki lo sishakach mi’ pi zaro, ‘For it (the Torah) will not be forgotten’ – ever.” We will always learn the Torah! We will never forget it.