Back to Ego, again, but doesn't that define life?

Rabbi explores the next step in the Judah/King David journey, wondering why it is that Yaakov entrusts Benjamin with Yehuda and not Ruben?

Responsibility is the foundation for leadership.

What makes Judah the most trustworthy son of his father Jacob?

It is because he submits his entire being under that responsibility, he becomes the vessel to succeed in the mission he’s entrusted with because he negates himself so powerfully.

Jacob can’t bring himself to trust Ruben with the dangerous and consequential mission, as he is worried that Ruben will mix himself into the picture, and fail to bring his entire self to bear on the problems that the Egyptians will surely throw their way.

Under fire, fears of failure, even legitimate ones, will hinder one's ability to focus everything they’ve got, and under fire you’d better have access to all your strength and focus.

Juda, with no self in the picture, is able to decide exactly when to push Yaakov to part with Benjamin. He isn’t rash. He has no need to act if it won’t be 100% useful, and so he waits, patiently, for the perfect opportunity, and he gets one when the food supplies run dry.