America's education system is facing daunting challenges of equity, engagement, and excellence. However, due to the increasing demands of being an educational leader, it is evident that no one person can address all the complex roles and responsibilities required of such positions today. Thus, an important component of the response to these challenges is redefining school leadership as a more distributive model. Beyond administrative skills, strong leadership is critical to addressing the disparities in our education system and developing collaborative advocacy (internal and external) for enhancing the quality and rigor of academic studies for all students. This article addresses educational leadership by first considering an earlier transformational period in our school system. It then focuses on some of the cultural, economic, and political challenges that will redefine education and schooling in the 21st century and why we need to develop new models of school leadership. Just as transformative changes were made a half century ago, so they can and must be made now.