Despite the popularity of leadership education on college campuses, little is known about what individual participants learn and remember. This longitudinal study examines the impact of a leadership education retreat through the eyes of six undergraduate college men. Entry and exit interviews, along with intensive one and two year follow-up interviews, were conducted. Cross case analysis reveals that leadership identity was reshaped by perceived personal failure during crisis. Longitudinal analysis suggests that students attribute improved leadership capabilities less to leadership education than to their own development and leadership experiences. This study questions the value of stand-alone or short-term leadership education models and suggests new curricular approaches to leadership education that incorporate potential future crucible experiences.