Issachar is Leah's fifth son, born after the episode of the mandrakes (Genesis 30:14 to 17). Leah says: "G-d has given me my reward, because I gave my maidservant to my husband" (Genesis 30:18). The name carries the word sakhar, wage, reward.
Jacob describes him this way: "Issachar is a strong-boned donkey, lying down between the sheepfolds. He saw that rest was good and that the land was pleasant, and he bent his shoulder to bear" (Genesis 49:14 and 15). One may read in it the image of a strength that accepts the load; the verse itself speaks of a shoulder bent willingly.
Moses blesses him together with Zebulun: "Rejoice, Zebulun, in your going out, and you, Issachar, in your tents" (Deuteronomy 33:18). Chronicles adds: "of the sons of Issachar, men who had understanding of the times, to know what Israel should do" (I Chronicles 12:33).
On the breastplate, according to the Targum attributed to Jonathan, which follows the order of birth, his stone is the last of the third row, the achlamah (Exodus 28:19), often rendered as amethyst; the identification remains uncertain. In the desert Issachar encamps to the east, next to Judah (Numbers 2:5), with Nethanel son of Zuar as prince. The Midrash cited by Ramban explains this neighborhood: in the east whence light comes, next to the king, stands Issachar, who carries the Torah. According to Rashi, his banner had the color of his stone.
According to the order of the banners, Issachar receives Iyar, the month of the letter Vav (Sefer Yetzirah 5:2); in the Vilna Gaon's version, Vav rules over thought. The Bnei Yissaschar, whose very title comes from this verse of Chronicles, links Iyar to Issachar through these men "of understanding," and notes that the month's combination is that of the intellect. The Shem MiShmuel, following the order of the Ari, sees in it the time of Torah after Nissan, the time of deeds. According to the order of birth, Iyar would go to Simeon.
Keep this: Issachar is a mother's reward, and he receives the tent of study. His strength lies in the shoulder that carries and in the understanding that knows what must be done.