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Genesis 44:29
ESV If you take this one also from me, and harm happens to him, you will bring down my gray hairs in evil to Sheol.’
NIV If you take this one from me too and harm comes to him, you will bring my gray head down to the grave in misery.’
NASB If you also take this one from me, and harm happens to him, you will bring my gray hair down to Sheol in sorrow.’
CSB If you also take this one from me and anything happens to him, you will bring my gray hairs down to Sheol in sorrow.’
NLT Now if you take his brother away from me, and any harm comes to him, you will send this grieving, white-haired man to his grave. ’
KJV And if ye take this also from me, and mischief befall him, ye shall bring down my gray hairs with sorrow to the grave.
NKJV But if you take this one also from me, and calamity befalls him, you shall bring down my gray hair with sorrow to the grave.’

What does Genesis 44:29 mean?

Judah is describing his father's response to risking his youngest and favorite son, Benjamin. This is part of his plea to an Egyptian governor (Genesis 44:18–28), who has demanded Benjamin remain behind as a slave (Genesis 44:17), after finding his personal silver cup in Benjamin's bag (Genesis 44:12–14). Jacob had said that if any harm were to come to Benjamin, his only remaining son by his beloved wife Rachel (Genesis 35:24), Judah and his brothers would be responsible for bringing Jacob's gray hairs "to evil in sheol" (Genesis 42:38).

At this point in Israel's history, sheol was used as a generic term for the afterlife. Judah is making it abundantly clear to that losing his beloved Benjamin would kill their father. He does not know that the man he speaks to is also a son of Jacob (Genesis 42:7–8). This is Joseph, the long-lost one sold into slavery by Judah and the other nine older brothers twenty years prior (Genesis 37:24–28).
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