In response to the hitherto unchallenged assumptions supporting a globalized economy, the Leadership for Sustainability Education (LSE) program, formerly Leadership in Ecology, Culture, and Learning, was developed as part of an emerging sustainability movement. This article highlights the favorable conditions that provided the context for the evolution of the LSE program, including organizational policies and practices at Portland State University, and a commitment to community-university partnerships that conveyed the University’s motto, “Let Knowledge Serve the City.” We discuss the potential that higher education has to transform practices and ways of thinking necessary for ecological sustainability and social justice. Following this overview, we outline the main elements of the LSE Master’s degree program, including the four key learning areas: self-understanding and commitment, systemic view of the world, bio-cultural relationships, and tools for sustainable change. Additionally, we describe the types of learning experiences and assessment strategies employed throughout the program. We conclude by sharing the key authors and thinkers who influence the program and coursework.