Genesis 49:14

Issakar is an ass in the law; a strong tribe, knowing the order of the times; and he lieth down between the limits of his brethren.

יששכר חמור גרם, he is not like Zevulun who engages in voyages with mariners to distant lands to engage in trade and commerce. He stays at home toiling his earth sharing the fate of his donkeys, his beasts of burden.

בין המשפתים at the outer edges of town, where the surrounding fields are under cultivation. We encounter the expression for tilling the soil as applying not only to oxen but also to donkeys in Isaiah 32,20 אשריכם זרעי על כל מים, משלחי רגל השור והחמור, “happy shall you be who sow by the waters, who send out oxen and donkeys to plough and spread the seed.” We find a similar contrast between these two tribes expressed in Moses‘ blessing in Deut. 33,18שמח זבולון בצאתך ויששכר באהליך “enjoy your departures (on voyages) Zevulun, and you, Issachar, enjoy your pursuing your vocation in your tents.”

יששכר חמור, not ready to fight a war. This corresponds to the saying of the sages in Avodah Zarah 17 אי ספרא לא סייפא, “if your vocation is books, it cannot be skill with a sword.”

גרם. A donkey with strong bones. And, due to his strength, רובץ בין המשפמים when he lies down to rest, he does so between two שפיתות, open type of containers able to contain the loads that he will carry. These are placed on either side of him. [the word seems to describe a recessed setting such as on a stove which has holes into which the pots are lowered to be surrounded by the fire underneath. Ed.] The unique nature of this kind of stove is that the pots are not capable of being moved or removed from it until the cooking or boiling is complete and the fire has gone out. Yaakov describes a simile in which Issachar, i.e. the donkey can hold out until he has completed the job assigned to him. The whole verse is a parable symbolising how Issachar accepts the yoke of the Torah and studies Torah with all the energy at his command. He does this in addition to shouldering the burden of derech eretz, i.e. doing justice to the more mundane demands made upon everybody living on this planet.

יששכר חמור גרם, like a strong donkey possessing strong bones. He is able to lie down while carrying his load and to get up again while still having his load on his back.

המשפתים, a reference to the load the donkey carries. Yaakov uses the word in the plural mode, to indicate that Issachar will be loaded with not only one burden but two, carrying one on his right side, the other on his left. His soil will be extremely good, as if to say that he will not join battle formations in war but will belong to the troops bringing the supplies to the front lines. He will pay a special tax to the king to be allowed this arrangement, hence ויהי למס עובד. This is what Yaakov had in mind when he said of Issachar וירא מנוחה כי טוב. Our sages in Bereshit Rabbah 98,12, and 99,10 explain the entire blessing as a prophecy that Issachar would make his primary occupation the study of Torah, and Yaakov depicting such a way of life as something lovely and rewarding for those who pursue it. The more one labours and immerses oneself deeply in Torah study the greater the ultimate sense of serenity, מנוחה, constructive peace of mind one will experience. All the expressions used here such as וירא מנוחה כי טוב ואת הארץ כי נעמה ויט שכמו לסבול ויהי למס עובד, describe, step by step the immersion in Torah study, the difficulties in mastering that discipline, and the eventual satisfaction it yields the person who stays the course. As proof that Yaakov’s blessing for Issachar did indeed come true, consider that the tribe of Issachar sent only 200 representatives to attend the crowning of David as King, whereas all the other tribes sent delegations numbering between 10,000 and 120,000. The 200 men from Issachar however, are described as יודעי בינה לעתים, “knowing how to interpret the signs of the times.” They were all Torah scholars. (compare Chronicles I 12,24-38)

יששכר חמור גרם, “Issachar is a bony donkey;” in the Talmud tractate Niddah, folio 31 this line is understood as Yaakov saying that a bony donkey was the cause of Issachar having been born. How so? When Yaakov came home from the field and Leah heard the donkey he was riding on braying, she went out of her tent to meet him and brought him to her tent. During that night she became pregnant with Issachar. (B’reshit Rabbah 99,10)