It is clear already from the sale of Yosef, that Yehuda had leadership potential. It was he who convinced the brothers not to murder Yosef, something his older brother Reuven was unable to do. Sadly, this display of leadership was for negative purposes and realizing this Yehudah left the family, married a Canaanite woman – a definite no-no and a one-way ticket to being ousted from the covenant – consorts with whom he thought was a prostitute. His great potential was in danger of being lost to the Jewish people.
Yet gathering up moral courage he admitted his sin and reunited with 10 of his brothers. It was he who convinced his father to allow Binyamin to go to Egypt – something his older brother Reuven was unable to do. And faced with the possibility of Binyamin taken captive in Egypt it is Yehuda who “approaches” Yosef to plead the case as to why he should let Binyamin go. Like a seasoned politician he mixes fact and fiction as he makes his case, hoping to move Yosef emotionally.
“Your servant, my father, said to us, ‘As you know, my wife bore me two sons'” (Breisheet 44:27). This claim is obviously not true. Yaakov had at least 13 children, not two. Yet if one understands isti, my wife, as referring to “my one and only true wife”, Rachel, it may be literally true, but the claim that Yaakov said so must be false. After everything the family has been through is it conceivable that Yaakov would tell his children – born to Leah, Zilpha and Bihah – that the only wife that matters is Rachel and the only children he truly loves are Yosef and Binyamin? Even if that is how Yaakov felt – a big if – would he ever say so?
Sadly, our patriarchs and matriarchs displayed favouritism towards their children, something for which they paid a heavy price for. Putting these words in Yaakov’s mouth makes for a good argument. If Binyamin does not come home alive, father will die. Yehuda understood that if one wants to convince someone of something, if one wants them to change their mind, intellectual arguments, as true as they may be, are unlikely to have much impact. It is the heart, not the mind that moves people. Yaakov is at home worried that he made the wrong decision in allowing Binyamin to go down to Egypt. We might be guilty of stealing, but are you going to let an old man die over a goblet. A broken heart can go a long way.
While we the reader can see the mistruth spoken by Yehuda, perhaps he was expressing the “truth” as he understood it. Of course, everyone – Yosef included – knew that there were 12 brothers and the youngest was at home lest he be harmed. While the others could risk their lives, Binyamin could not. The favouritism shown first to Yosef and now to Binyamin made the other brothers truly feel that Yaakov had but one wife and two children. This claim was truer than even Yaakov realized.
At the same time, Yehuda understood that “one cannot compare hearing to seeing”. There were no pictures of an aged man crying over his losses. Yaakov – or so Yehuda thought – was an abstract, unknown person as far as Yosef was concerned. But I, Yehuda, who is standing right before you, swore that I would bring Binyamin home. “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!”. How, master, can you allow me who stands before you to suffer such?
Yehuda was successful in his mission. And it is success that is the most important measure of a leader. While success is not always within one’s control, great leaders are successful more often than not. That is what makes them great. Those who do not succeed are – or should be – replaced. Such are the demands of leadership.
Yehuda not only convinced Yosef, he also convinced his father, that he would be the leader of the nation. “Judah is a lion’s whelp; on prey, my son, have you grown. He crouches, lies down like a lion. Like a lioness —who dares rouse him? The scepter shall not depart from Judah, Nor the ruler’s staff from between his feet; So that tribute shall come to him. And the homage of peoples be his” (Breisheet 49:9-10).
May we merit the leadership of “Yehuda”, one who learns from their mistakes, takes responsibility and knows how to interact with world powers with the proper mix of deference yet firmness.
 Rav Shimshon Raphael Hirsch goes so far as to claim that had Yitzhak and Rivka not let their respective favouritisms impact on how they raised their children, they likely would have been able to keep Eisav within the covenantal community.