Using Personal Tragedy For Growth
Judah's plea to Joseph is a sign of his personal growth and ability to empathize with his father's grief.
It's not that God took away Judah's children because of what he might have done to Jacob--that would be cruel and capricious on God's part. Rather, the midrash tells us what made their reconciliation possible: Judah's ability (or willingness) to empathize deeply with his father's experience, his "knowing the pain of children." Empathy ideally leads to compassion, and it seems Judah's compassion was so great that he could not let his father again lose a favored younger son.
This begs a further question: why should Jacob be more bereaved at losing Benjamin than at losing Judah, since the whole point of Judah's speech is that he will stay in Egypt as a substitute?
Whether it was because Benjamin was the youngest, or because he was a son of the beloved wife Rachel, Judah knew that Jacob had a special relationship with him, as he had once had with Joseph. (Cf. 44:30) This fact is what makes Judah's compassion so extraordinary--not only was he able to empathize with a bereaved father, but he was even able to overcome his previous resentments to do so, perhaps even forgiving his father for loving his sons unequally.
This is the measure ofJudah's greatness: that he didn't remain mired in his pain but grew spiritually out of it, taking tragedy and using it as the soil for empathy, compassion, forgiveness, and self-sacrifice. He was the one to step forward when the hour demanded it because he was the one who knew that to redeem himself out of his own past mistakes and accumulated grief, he had to extend himself for the redemption of others.
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