Recently, the ‘Smart City’ label has emerged as a popular umbrella term for numerous projects around the world that claim to offer an enhanced urban experience, often provided in collaboration with international companies through private-public partnerships. As smart cities pledge to create long-term economic sustainability and progressive form of urban entrepreneurialism, it is getting important to highlight risks such as the reduced role of the public sector, technological dominance and data privacy.In contrast to more a conventional, long-term, holistic master planning, a technologically pre-determined form of Smart City endangers the emancipator usage of public spaces as spaces of diversity, creativity, inclusive citizen participation and urban sustainability.This research approaches the concept of Smart Cities as a future category and, thus, targets to develop a comprehensive visual analysis based on architectural representations in the form of computer-generated images (CGI’s). The Quayside project, a notable and widely criticized urban development project, by Sidewalk Toronto, a cooperation between Waterfront Toronto and Sidewalk Labs which is a sister subsidiary of Alphabet Inc., has been selected as Smart City case study as. Visual analysis was conducted by using the theoretical frame advocating ‘Coordinating Smart Cities’ in contrast to ‘Prescriptive Smart Cities’ by Richard Sennett. In addition to Sennett’s concept of ‘Incomplete Form’, Jan Gehl’s ‘Twelve Quality Criteria’ was used as coding categories to elaborate the content analysis which was followed by semiological and compositional interpretations. Visuals have been investigated in three sequential sets and analyzed focusing on time-based comparative frequency counts for sets of visuals. Concentrating on how future public spaces are illustrated, the study aims to uncover and to discuss how Smart Cities are being imagined and advertised.