Parashat Va-Yigash begins with a plea by Yehudah to the ruler of Egypt, in which he offers to substitute as a slave for Benjamin. He openly tells the ruler of Benjamin’s special place in Jacobs’s affections, fully validating it.

My lord asked his servants “Have you a father or another brother?” We told my lord, “we have an old father, and there is a child of his old age, the youngest; his full brother is dead, so that he alone is left of his mother , and his father dotes on him (Genesis 44:19-20).

Yehudah goes on to describe how they were compelled to bring Benjamin to Egypt, for they would have starved otherwise, and openly recall as well their father’s mention of his unbearable pain at the apparent demise of Joseph.

As you know, my wife bore me two sons. But one is gone from me, and I said: “Alas, he was torn by a beast! Nor have I seen him since. If you take this one from me too, and he meets with disaster, you will send my white head down to Sheol in grief” (Genesis 44:27-28).

Yehudah concludes: “Now, if I come to our servant my father and the boy is not with us- since his own life is so bound up with his- when he sees that the boy is not with us, he will die, and your servants will send the white head of your servant our father down to Sheol in grief. Now, your servant has pledged himself for the boy to my father, saying, ‘If I do not bring him back to you, I shall stand guilty before my father forever.’ Therefore, please let your servant remain as a slave to my lord instead of the boy, and let the boy go back with his brothers. For how can I go back to my father unless the boy is with me? Let me not be witness to the woe that would overtake my father!” (Genesis 44:30-34).

Yehudah was willing to undergo personally the exact same type of fate that he had inflicted upon Joseph. He was willing to be all alone as a slave in a foreign country, separated from the rest of his brothers. When he made this remark, he had indicated that he truly realized how horrible his previous behavior as a “bully” to Joseph was and was prepared to undergo full penance. One is reminded of the doctrine of the medieval Hasidei Ashkenaz called teshuvat ha-mishqal. According to this doctrine, when one repents of a sin, one must not only repent of the deed, but of the feelings of lustful pleasure that accompanied the deed. Carrying the analogy to the case at hand, Yehudah was offering to undergo teshuvat ha-mishqal for the bullying that he had participated in.

Of course, the ruler of Egypt now identifies himself as…Joseph! And of course, he does not demand that Yehudah actually undergo the pain. His intent from the outset was
to see that his brothers had repented from their previous behavior towards him. After he saw that the brothers had indeed changed, he could joyfully say, “Now hurry back to my father…you will dwell in the region of Goshen, where you will be near me- you and your children and grandchildren, your flocks and herds, and all that is yours.” (Genesis 45:9-10).

The Rambam in Shemoneh Peraqim, the introduction to his commentary on Pirqei Abot, distinguishes between the man who is naturally righteous on the one hand, and the man who must struggle to overcome his inclination for sin on the other.

Maran Ha-Rav Joseph B. Soloveitchik, zatzal, utilized these categories to draw contrasting pictures of Joseph, the natural tzaddiq, on the one hand, as opposed to Yehudah, who had to struggle with his nature to achieve moral purity, on the other. But Yehudah does not fail. On the contrary, he emerges victorious in his battle with himself! The proof text that the Rav gave for Yehudah, was Genesis 38, which depicts his original behavior towards Tamar and his subsequent repentance.

For my part, I would fortify this with the aforementioned passage from the beginning of Parashat Va-Yigash. This Parashah provides the quintessential example of Yehudah’s ability to transform himself as a human being. Originally, as part of the gang of bullies that had hurt their younger brother, he had been responsible for the sale of Joseph. But in his final plea to the ruler of Egypt, he offered himself to be the slave. (And for the reader of the parashah, who knows beforehand what the brothers are about to discover, there is another deeply ironic point: Yehudah is offering to be the slave of his own victim!) Judah completes a magnificent transformation of his character. From a moral/religious point of view, it is indeed appropriate that one with such character traits should be blessed with progeny that will be Kings of Israel.