This paper examines the sensitivity of Stafford Beer’s Viable System Model of organization to the concept of human freedom. The paper notes the many critics who have suggested that the Viable System Model is inimical to human freedom and their especial reference to its application to the social economy of Chile in the early 1970s. Drawing on the work of philosophers, a conceptual analysis of freedom is provided that suggests a complex ordinary language usage of the term. At least three determinants of freedom, that are logically independent of one another, are identified as being of relevance to its ordinary usage. The paper finds that these determinants are implicitly addressed and acknowledged within Beer’s own writings, but that they are ignored by the critics of the Viable System Model and that this makes for a lack of clarity and precision in the debate. The paper also applies a further criterion, formulated in political philosophy, to judge whether the leadership of the government that applied the Viable System Model to the Chilean social economy was itself hostile to political freedom or democracy. This application of the criterion suggests that they were not.