Before his death, Jacob gathered his sons to him and gave them each a blessing that specifically reflected their personalities and their futures. To Issachar, Leah’s fifth son, Jacob said: “Issachar is a strong-boned donkey, crouching between the saddlebags. When he saw how good security was, how pleasant the country was, he bent his shoulder to the burden."
The sages have interpreted this verse to be an allusion to the tribe of Issachar’s future scholarly role. The “security” alluded to in the verse was the partnership that the tribe of Issachar had with the tribe of Zevulun, who supported the tribe of Issachar and shared in the spiritual reward of their Torah study.
Although we don’t find any descriptive elements about Issachar’s life in the Torah, the story of his conception is well-known.
One fine day during harvesting season, Reuben brought his mother a bouquet of dudaim (mandrake) a flower reputed to aid fertility. When Rachel. who was childless, saw the dudaim, she immediately requested some from Leah, her sister.
“Was your taking my husband insignificant? Now you want my son’s dudaim as well?” Leah responded, underscoring how much more Jacob loved Rachel than Leah, and that Jacob maintained his bed in Rachel’s tent even though Leah had borne him children.
Rachel hated to see her sister so unhappy. “In return for your son’s dudaim, he [Jacob] shall lie with you tonight,” she offered. That evening, Leah heard the braying of Jacob’s donkey (Genesis Rabbah 99:10) and went out to meet Jacob and told him that he was to come to her tent that night.
Leah’s zealousness to be with Jacob was rewarded, and she found herself pregnant once again. Leah called her fifth son Issachar, saying “God has granted me my reward because I gave my maidservant (Zilpah) to my husband.”
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