Much of the narrative of the conclusion of Bereishit is dominated by the struggle between Yehuda and Yosef. Yet a third - and more natural candidate- is discarded without the drama surrounding his brothers. Why is Reuven stripped of his natural license, ceding leadership to his two younger brothers? By closely exploring the characters of Yehuda, Yosef, and Reuven, we can understand why Reuven was deemed unworthy to be a leader, and learn about the importance of failure, guilt, and forgiveness in leadership.