Henry David Thoreau, Susan B. Anthony, W. E. B. DuBois, and Lyndon B. Johnson are just a few of the famous Americans who taught. They resisted the fantasy of educators as saints or saviors, and understood teaching as a job in which the potential for children’s intellectual transcendence and social mobility, though always present, is limited by real-world concerns such as poor training, low pay, inadequate supplies, inept administration, and impoverished students and families. These teachers’ stories, and those of less well-known teachers, propel this history forward and help us understand why American teaching has evolved into such a peculiar profession, one attacked and admired in equal proportion.