This article examines the architectural thought of Louis Sullivan, commonly regarded as the prophet of architectural modernism and the inspiration for the stark Chicago-style skyscraper. Sullivan regarded sociology to he the most urgent of the disciplines as America sought to realize its democratic promise. Animated by certain understandings of self and community that would later define the Chicago School of Sociology, Sullivan saw himself as a kind of social engineer whose architecture would generate democratic space and encourage authentic interaction. Chicago was his laboratory where he fervently called for the escape from the fetters of tradition in order to give form to a democratic present. While the movement he helped inspire reshaped the landscapes where humans labored and lived, few today would confuse the architectural space of a skyscraper, or architectural modernism in general, with the cultivation of authenticity; even fewer would confuse modernism and the sky-scraper with the fulfillment of democracy. Sullivan’s unbridled hopes lor the future have been quelled by postmodern criticisms of the spatial dynamics he espoused. It is argued that this dramatic sea change was a function of a fundamental Haw in Sullivan’s social theory. Following Leo Strauss, it is argued that implicit in Sullivan’s famous dictum“form follows function” was the collapse of the distinction between the real and the ideal. This undermined Sullivan’s voice while framing his sense ol democracy in strictly processional terms. In the end, Sullivan sought an architecture according to which control over circumstance served no higher purpose save control, an architecture whose escape from the past concealed from view the kind of direction that could lend meaning to the control Sullivan was desperate to secure. It is suggested that sociologists are not unlike Sullivan, and that their calls for autonomy and empowerment speak to process and movement rather than ends or destinations.