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Issachar Chose the Simple Life and Called It Wisdom

While his brothers sought power, Issachar farmed. His testament reveals why singleness of heart was the most radical choice a patriarch could make.

Curated by Arthur · Told by Maggid ·
Table of Contents
  1. The Son Born From a Deal
  2. Singleness of Heart
  3. A Life Without Complications
  4. What He Offered His Sons

The Son Born From a Deal

Issachar entered the world as the result of a transaction. His mother Leah had traded his father Jacob to his other mother Rachel for a night, exchanging mandrakes she had found in the fields in return for the right to sleep with her own husband. The Book of Genesis records this with the flatness of a ledger entry. Issachar's name is understood in the tradition to mean reward, the fruit of what Leah had paid. He was the dividend of a negotiation over fertility between two women who shared a tent and a husband and almost nothing else.

He spent his life refusing to negotiate.

Singleness of Heart

The testimonies his brothers left to their children were full of the texture of experience: Reuben and his seven years of fasting, Judah and the lions he had killed and the staff he had surrendered, Levi and the vision over Abel-Meholah, Dan and the sword he had held over his brother's head. These were men who had been tested by power and desire and guilt and vision. They had suffered and failed and recovered and suffered again. They had things to confess.

Issachar's testament is almost without drama. He farmed. He gave the firstfruits of his labor to the priest, then gave to his father, then kept what remained for himself. He did not marry until he was thirty years old, not from ascetic principle but from exhaustion: the fields consumed him during the day and sleep took him at night before desire could find him. His father blessed the simplicity of this. He understood it as a form of strength, not a form of passivity.

A Life Without Complications

He did not know envy. This is not a claim the other patriarchs made for themselves. Dan confessed that he had held a sword over Joseph's head from envy. Reuben confessed that guilt over his own transgressions had lived in him for years like a bone under the skin. Judah catalogued the ways that desire had bent his judgment. Issachar said: I did not know envy. He said it plainly, as a man reports weather.

He did not deceive anyone. He did not set himself against a neighbor for gain. He did not allow his eyes to collect the things that belonged to other people. He kept his heart pointed in one direction at a time, which is what the tradition means by singleness of heart, and the simplicity of that practice meant that he almost never found himself in a situation where he had to choose between competing obligations or manage the consequences of a desire he had fed too long.

In a family where nearly every major story is a story about what happens when a person's interior becomes complicated, Issachar's refusal to become complicated was itself a kind of achievement. It was not an absence of character. It was a specific choice about what to put in the center of a life and what to leave at the edge.

What He Offered His Sons

On his deathbed Issachar told his sons to love the land. He told them to labor in it until their backs bent and their hands cracked, and not to feel ashamed of the work. He told them to offer the firstfruits before they ate. He told them to keep the law of Moses, to fear the Lord, to love their neighbor. He said that the one who lived this way would have no enemies in the world, because a man who wants nothing from anyone else has nothing that can be used against him.

This is the radical claim buried inside the testimony of the simplest patriarch: that singleness of heart is not the absence of ambition but the form of ambition that leaves you the least exposed. The brothers who had hungered for more had found themselves in complicated situations requiring complicated choices. Issachar had farmed, given the firstfruits, gone to sleep, and woken up without new enemies. He was not unintelligent. He was disciplined about what he allowed himself to want.


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The texts this telling draws on, in full. Open a card to read inline, or expand it for a wider, quieter read.

Legends of the Jews, II. The Sons Of Jacob, Issachar's Singleness Of HeartLegends of the Jews

The familiar telling remembers the big names – Abraham, Moses, David. But what about the seemingly quieter figures, the ones whose stories whisper rather than shout? the life of Issachar, one of Jacob's twelve sons.

His story, as recounted in Ginzberg’s Legends of the Jews, isn’t one of dramatic battles or prophetic pronouncements. Instead, it’s a story of simplicity, of integrity, and of a "singleness of heart" that earned him divine favor.

Issachar’s very birth is intertwined with a fascinating tale. Remember the dudaim? Those "fragrant apples" (some say mandrakes) that Reuben, Leah's son, found in the field? The story goes that Rachel, Jacob's beloved but barren wife, desperately wanted them. Leah, in exchange for letting Rachel have them, bargained for a night with Jacob. As the story goes, she felt that since she was already married to Jacob, she was entitled to his attention. "Jacob is mine, and I am the wife of his youth!" she exclaimed (Ginzberg referencing the Midrash (rabbinic interpretive commentary)). And so, Leah conceived Issachar.

In Ginzberg's retelling, an angel appeared to Jacob and explained that Rachel would only have two sons, because she chose continence, while Leah would bear six, because she desired to be with her husband, not because of evil inclination, but for the sake of children. Rachel did not even eat the dudaim, but put them in the house of the Lord, and gave them to the priest.

Later in life, Issachar followed a simple path: tilling the land, bringing the first fruits to the priest, and then sharing the rest with his family and the needy. He married late, at thirty years old, because his hard work consumed his strength. His father, Jacob, recognized his yosher lev – his "singleness of heart" – and blessed him. Why? Because Issachar’s sincerity was so complete that God aided him.

As Issachar felt his end approaching, he gathered his sons and imparted his wisdom. His message? Embrace simplicity. Shun greed. Avoid envy and lust. Focus on honest labor and acts of kindness. "Walk in singleness of heart," he urged them, "for upon it resteth the favor of the Lord at all times." He contrasts this with a warning about the future. A future where his descendants would abandon probity, pursue craftiness, and forsake the commandments of the Lord, as Ginzberg draws from tradition.

Issachar's final testament is a powerful declaration of his own blamelessness. "I am one hundred and twenty-two years old," he proclaims, "and I can discern no sin in myself." He had no relations with a woman save his wife, he avoided wine to prevent being led astray, and he never coveted what belonged to another. He loved the Lord with all his might and loved mankind as well.

He instructed his sons to bury him in the Cave of Machpelah in Hebron, alongside his forefathers. He then passed away peacefully, full of years and in possession of all his faculties.

What can we learn from Issachar's life? Perhaps it's a reminder that holiness isn't always about grand gestures or extraordinary feats. Sometimes, it's found in the quiet moments, in the simple acts of kindness, and in the unwavering commitment to integrity.

Issachar’s life challenges us to examine our own hearts. Are we striving for that "singleness of heart?" Are we cultivating simplicity in a world that constantly demands complexity? It’s a question worth pondering, isn’t it? A question that might just lead us closer to the divine favor that Issachar so beautifully embodied.

Full source
Legends of the Jews 2:47Legends of the Jews

The tradition is rich with details, offering us glimpses into their lives and legacies.

The scene: Issachar, nearing the end of his long life, gathers his children. He instructs them to carry him to Hebron, that ancient and sacred city. He wants to be buried alongside his fathers in the Cave of Machpelah, the resting place of Abraham, Isaac, and Jacob – a place of immense significance in Jewish tradition.

Then, the verse tells us, "he stretched out his feet, and fell into the sleep of eternity, full of years, healthy of limb, and in the possession of all his faculties.” What a beautiful image of a peaceful passing, a life lived fully and completely.

Let's shift our focus to Zebulon. He lived to the ripe old age of one hundred and fourteen, passing away just two years after Joseph, the brother they had once betrayed. Before his death, Zebulon calls his sons together, just as his brother Issachar had done. But instead of burial instructions, he imparts a powerful moral lesson.

According to Legends of the Jews, a compilation of rabbinic lore collected by Louis Ginzberg, Zebulon reminds his sons of his name’s significance. "I am Zebulon," he says, "a precious gift for my parents, for when I was born, my father became very rich." He’s referring back to the story of Jacob's clever use of streaked rods to increase his flocks while working for his father-in-law, Laban (Genesis 30:37-43). Zebulon’s birth was a turning point, a moment of prosperity.

Zebulon then makes a striking declaration: "I am conscious of no sin in me, and I remember no wrong done by me…" That's a bold statement! But immediately, he qualifies it, acknowledging a deep regret: “unless it be the unwitting sin committed against Joseph."

Here, Zebulon grapples with the weight of the past. He admits that he didn’t reveal to Jacob what had happened to Joseph, even though he mourned in secret. Why? Because he feared his brothers. “They had agreed,” he says, “that he who betrayed the secret should be slain with the sword.” Imagine the fear and the moral conflict! He knew what they had done was wrong, but he was afraid to speak out.

He continues, "When they planned to kill Joseph, I besought them amid tears not to sin thus." So, he wasn't entirely complicit. He tried to stop them. He pleaded with them. But ultimately, he was unable to prevent the tragedy.

Zebulon's final words to his sons are a poignant reminder of the complexities of family, the burden of secrets, and the enduring power of regret. He acknowledges his failings, not to wallow in them, but to teach his sons a valuable lesson: to live a life of piety, a life free from the kind of moral compromises he was forced to make.

These small glimpses into the lives of Issachar and Zebulon, drawn from the tradition of Jewish legend, offer us a deeper understanding of these biblical figures. They remind us that even the sons of Jacob were flawed, human beings confronting difficult choices and living with the consequences of their actions. Their stories, passed down through generations, continue to resonate with us today, inviting us to reflect on our own lives and the choices we make.

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