This book explores the evolution of community college leadership imaginaries. Drawing insights from cultural political economy and critical discourse studies, it defines leadership imaginaries as constellations of meanings used to navigate a complex institutional reality. The main thesis of the book is that during the second half of the 20th century, leadership imaginaries evolved in relation to ideological contests and political-economic crises. Chapters on topics such as leadership, mission, vision, and crisis interrogate the unwritten rules about what administrators must do to be "good" leaders. Once these unwritten rules are made explicit and connected to ideological processes, it becomes apparent that leadership work does not have to be the way it is. Problematizing the status quo, we call for community college leaders, mentors, researchers, and other stakeholders to reimagine leadership and leadership work.