What does Genesis 37:29 mean?
ESV: When Reuben returned to the pit and saw that Joseph was not in the pit, he tore his clothes
NIV: When Reuben returned to the cistern and saw that Joseph was not there, he tore his clothes.
NASB: Now Reuben returned to the pit, and behold, Joseph was not in the pit; so he tore his garments.
CSB: When Reuben returned to the pit and saw that Joseph was not there, he tore his clothes.
NLT: Some time later, Reuben returned to get Joseph out of the cistern. When he discovered that Joseph was missing, he tore his clothes in grief.
KJV: And Reuben returned unto the pit; and, behold, Joseph was not in the pit; and he rent his clothes.
NKJV: Then Reuben returned to the pit, and indeed Joseph was not in the pit; and he tore his clothes.
Verse Commentary:
After securing Joseph in the pit, Reuben seems not to have stayed to eat with his brothers (Genesis 37:18–25). He seems to have missed the exchange recorded in the last few verses, in which Judah talked his brothers into selling Joseph as a slave to passing traders (Genesis 37:26–28).

When Reuben returns to check on Joseph—perhaps to free him and return him to their father—he finds the pit empty. Heartbroken, Reuben tears his clothes in a sign of grief. Unlike the modern era, where people often see clothes as disposable, garments in the ancient world were meant to last. Tearing one's clothes was both an act of sacrifice and a clearly visible sign of mourning. Reuben is deeply upset by what has happened.

Depending on his motives for rescuing Joseph, this might be selfish grief. It's possible Reuben saw rescuing Joseph as a way of redeeming himself, after defiling the family by sleeping with his father's concubine (Genesis 35:22). Now that opportunity is lost (Genesis 37:30).
Verse Context:
Genesis 37:12–36 describes how Joseph's wildly resentful brothers finally get rid of him. They hate Joseph for being Jacob's favorite (Genesis 37:3) and for his grandiose dreams (Genesis 37:5, 9). When Joseph arrives alone at the camp of his brothers, very far from home, they have an opportunity. Only Reuben's intervention keeps them from killing Joseph outright. Instead, while Reuben is absent, the brothers sell Joseph to passing slave traders and later convince their father he has been killed by a wild animal. Joseph becomes a slave in an Egyptian home. Genesis 39 will return to Joseph's story.
Chapter Summary:
Joseph, 17, is deeply loved by his father Jacob and deeply resented by his ten older brothers thanks to Jacob's favoritism. Jacob gives Joseph a princely robe, and Joseph reports dreams that predict his family will one day bow before him. When alone with Joseph in the wilderness, the brothers decide to kill him. Reuben stops them, suggesting they throw him alive into a pit, instead. While Reuben is gone, however, the brothers sell Joseph to slave-traders, later convincing their father Joseph has been killed by a wild animal. Joseph is placed in the home of an Egyptian nobleman.
Chapter Context:
Following the death of Isaac and the story of Esau's people, Genesis begins a section called the "generations of Jacob." The story will focus primarily on Jacob's son Joseph. Joseph is deeply hated by his brothers. While alone with him in the wilderness, they sell him to slave-traders, who take Joseph to Egypt. Chapter 38 details some of the scandals which happened while Joseph was gone. Genesis 39 will resume a focus on Joseph's experiences.
Book Summary:
The book of Genesis establishes fundamental truths about God. Among these are His role as the Creator, His holiness, His hatred of sin, His love for mankind, and His willingness to provide for our redemption. We learn not only where mankind has come from, but why the world is in its present form. The book also presents the establishment of Israel, God's chosen people. Many of the principles given in other parts of Scripture depend on the basic ideas presented here in the book of Genesis. Within the framework of the Bible, Genesis explains the bare-bones history of the universe leading up to the captivity of Israel in Egypt, setting the stage for the book of Exodus.
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