This chapter discusses Franco Basaglia’s anti-institutionalization project in Italian psychiatry during the 1960s alongside the Free School Movement that flourished during the same period across the United States. After analyzing the contradictions in Western societies and how they filtered into the realms of psychiatry and education, the chapter analyzes Basaglia’s proposal and the free school movement not only in relation to each other, but also against a wide panoply of psychiatric and educational alternatives that cropped up during the late 1960s and early 70s: Ronald D. Laing’s community households, Francesc Tosquelles’ extensive psychiatry, Alexander S. Neill’s Summerhill school, Ivan Illich’s and John Holt’s abolitionist position, and Paul Goodman’s experimentalism. Additionally, though distinct from Basaglia’s project, from the free school movement, and from the alternatives with which they are compared, the chapter places John Dewey’s philosophy at the center of the conversation, as a democratic standard that is used to assess the many institutional experiments that are covered.