In the parsha of Miketz, the Jacob and the brothers are confronted with a dilemna. Joseph, as the Viceroy is demanding that they bring Benjamin down to Egypt to corroborate the story they told initially upon seeing him. Shimon is kept in prison in Egypt. What to do? Reuven speaks first and says and says to Jacob when trying to convince him to allow them to go back: I will guarantee the safety of Benjamin. If he does not return with, kill my children. Of course, Rashi takes him to task and calls him a fool.
Interesting, later Yehuda also tries to convince Jacob. Here Jacob listens and relents. What is the difference? Yehuda convinces Jacob with these word:s : If I do not bring him back to you and stand him before you, then I will have sinned to you for all time.”
What is this talk of sin? The Shikker Dovid would like to suggest that the sin is his actions from before with Joseph and his failure to act as a brother. THe Shikker Dovid is sure that he is not the first person to say this. To the Shikker Dovid, this is an admission. He acknowledges his prior failure. Jacob sees this in his plea. This is why Yehuda is heeded and not Reuven.