Our parasha tells of the building of Yaakov’s family, one child at a time. We will concentrate on a look at the history of the tribes that emanated from the two last of Leah’s six children, Yissachar and Zevulun. These two, born significantly later than their older four full brothers, went down through history as a pair.
The older of the two, Yissachar, became the symbol for generations of one who earned the "crown of Torah." It is no surprise that in the section that deals with the gifts presented by the tribal leaders for the Mishkan, the leader of Yissachar was the second to bring his offerings. He followed right after Yehuda, the overall leader of the nation. The Midrash states that it was Yissachar’s excellence in Torah study that gave them this distinction (Sifrei Zuta 7). This greatness of Yissachar, which is only hinted at in the Torah, finds explicit mention in the Ketuvim: "From the sons of Yissachar, those who know wisdom of the times …" (Divrei Hayamim I 12:33). The midrash comments that this refers to "200 heads of Sanhedrin who came from the tribe of Yissachar" (Bereishit Rabba, Vayechi 99).
The Torah gives the following hint at the relationship between the tribes of the two brothers: "To Zevulun he [Moshe] said: Be happy, Zevulun, as you go out, and Yissachar in your tents" (Devarim 33:8). Chazal tell us (Bereishit Rabba ibid.) that Zevulun used to be involved in commerce and feed Yissachar. Ostensibly, Yissachar was involved in tzura (form, spirituality), which we consider most important, while Zevulun was involved in chomer (material matters), which is just a means at enabling the more important matters. However, looking at the blessings, both of Yaakov (Bereishit 49:13-14) and of Moshe (Devarim 33:18), we notice that Zevulun is mentioned first, even though Yissachar is older. Why?
The greatness of Yissachar can cause possible negative outcomes. One is that the lofty status of Torah scholars (sometimes referred to as kings – see Gittin 62a) can cause haughtiness. The other is that Yissachar may think that Zevulun needs him (for virtue) and he does not need Zevulun. Yissachar’s job is to close himself in quarters where he can concentrate on his studies and this can cause separation from people, which can be problematic in addition to being useful.
Yaakov and Moshe came to say that despite the importance of their holy activities, Yissachar must remember not to be haughty and not to overly separate themselves. "Despite your greatness, Yissachar, there are areas in which you are number two to Zevulun."
Shai Agnon’s short story, "Yissachar and Zevulun" demonstrates in his incisive mode of expression, how the two found each other in Gan Eden. There they found that Yissachar’s tally of Torah study virtues was less than he had thought and that the tally of Zevulun was greater than he thought. In any case, both were virtuous and complemented each other out for the betterment of the nation.