Yissachar is one of the more obscure of Yaakov’s sons. He never does anything seemingly unique and never appears to be mentioned as an individual. However, despite this unpretentiousness, Yaakov tells Eisav in Parashat VaYishlach, “VaYhi Li Shor VaChamor,” “I have oxen and donkeys” (BeReishit 32:6). The Midrash tells us that the bull is an allusion to Yosef, and the donkey is an allusion to Yissachar. These animal representations are found in the blessings that Yaakov confers to his sons on his deathbed in this week’s Parashah. Why, of all his twelve sons, does Yaakov single out Yissachar? Perhaps Yosef is quite an understandable choice. After all, he is the wonder-child, so to speak. He is highly learned and is the clear favorite of Yaakov. Who better to demonstrate to Eisav that Ya’akov has instilled good values in his children than the learned Yosef? Yet the question remains regarding Yissachar. He is never mentioned as anything more than just another brother. Why show him to Eisav rather than someone else, for example, Yehudah, the natural-born leader?
As Yaakov blesses Yissachar, Yaakov says (BeReishit 49:14), “Yissachar Chamor Garem,” “Yissachar is a strong-boned donkey,” and then the Torah states (BeReishit 49:15), “VaYeit Shichmo Lisbol,” “He bent his shoulder to bear.” As Rashi explains (ad. loc. s.v. LeMas Oveid), Yissachar is the bearer of the spiritual yoke of Torah learning. However, this only scratches the surface of the extent of Yissachar’s ability.
A donkey, the given attribute of Yissachar, is a pack animal that carries things around in the desert, much like a camel or a horse. A donkey is one of the more unfavorable creatures in the animal kingdom; if a donkey is carrying millions upon millions of dollars upon its back, it may be a wealthy donkey, but is still a donkey nonetheless, forced to degradingly carry a massive load on its shoulders. Why would anyone possibly want to be such an inauspicious creature as the donkey? The answer is that a donkey has a unique ability. Consider a different pack animal, a horse, which can carry heavy loads in the same manner as a donkey. When the horse needs to rest or take a drink, everything it was carrying has to be unloaded, and only then can it rest. A donkey, on the other hand, is able to rest with its load on its back, and even sleeps with its load on.
Yissachar is compared to a donkey, and as such has the qualities of a donkey. Like a donkey, he carries a load – Torah. Yissachar, out of all his brothers, has the unique ability to learn Torah and keep this load with him, even while he is relaxing or doing things that are not learning or otherwise religiously oriented. Now, with this information, Yaakov’s mention of Yissachar makes more sense. Eisav exemplifies the secular; he is “a man of the field.” The message of Eisav is to completely forget religion. This is first clearly shown when he trades his Bechorah to Yaakov. Therefore, who better to show to Eisav than Yissachar? Yissachar demonstrates to Eisav that the brothers will live Torah-filled lives (this is shown by Yosef as well). They might take occasional breaks, but the brothers will keep that Torah with them even as they relax. This is what Yaakov wants to imply to Eisav when he says that he has “oxen and donkeys,” and this is what Yaakov, in his blessing, entrusts Yissachar to teach the Jewish people.