Jacob has a problem. Sent on a mission to Egypt to procure provisions, his sons have returned minus a brother, and the price of Shimon's release is the presentation of Binyamin to the vizier of Egypt. Jacob has already lost a son - Joseph - to wild animals and Binyamin is all that remains to him of his beloved Rachel. Should he keep Binyamin at home, thereby consigning Shimon to a life of imprisonment in Egypt, or risk losing Binyamin in a ploy for Shimon's release?
Reuven, his first born, thinks he has a surefire way of reassuring Jacob of Binyamin's safe return:
Then Reuben said to his father, "You may kill my two sons if I do not bring him back to you. Put him in my care, and I will return him to you."
Unsurprisingly, Jacob does not respond well to this reassurance.
Faced with imminent starvation, Judah takes a stab at an argument to convince Jacob that he will do everything in his power to keep the youngest brother safe:
Then Judah said to his father Israel, "Send the boy in my care, and let us be on our way, that we may live and not die-you and we and our children. I myself will be surety for him; you may hold me responsible: if I do not bring him back to you and set him before you, I shall stand guilty before you forever."
Why is Judah's offer of eternal guilt more compelling than the lives of Reuven's children? Reuven assumes that vengeance would be Jacob's response to the loss of another son; Judah knows that eternal remorse is what a parent would feel, and he is willing to share in that remorse.
In Hebrew, the verb shakhol has a very limited meaning: to be bereft of a child. The language understands that there is no grief quite like the grief of a parent for a lost child, and Reuven has seen that grief in Jacob ever since the disappearance of Joseph was reported to him. He knows that empathy - not anger - is the key to convincing Jacob.
When we encounter people in pain, sometimes we respond with rationalizations, hoping to make the pain go away. But the pain will never go away, and the better response is to try to experience that pain, to share in its burden, and convey our empathy, friendship, and love: I see that you are in pain, and I will honor it and you.