This book bridges media, technocultural, urban and journalism studies to examine the role of journalism in relation to a smart city project on Toronto's waterfront. From the announcement of the public-private partnership called Sidewalk Toronto to the project's termination, a mediatized controversy unfolded. Through an assemblage approach to this project and a case study of the Globe and Mail and the Toronto Star, it follows the actors and chronicles the Quayside project story as a conversation about the promise and perils of a future "smart" neighbourhood. In addition to news of Waterfront Toronto, Sidewalk Labs, other actors, events and developments, there were multiple voices, views, interpretations and arguments, that manifested conflicting interests and values. As a situated actor, journalism produced a porous discourse where the prognostic value of the project to come could be expressed. The Quayside story not only clarified the nature of the project and the process with an active propose-and-public pushback movement but articulated relations of transparency and trust, governance and accountability. Journalist's work of mediation conditioned the project's emergence and dissolution within asymmetrical relations of power. In the public debate, Sidewalk Lab's bid for legitimacy would face an oppositional dimension that indented the project's enactment and modified its scope. Moreover, a time lag between project time and governmental policymaking made the mediatized controversy intractable. With their residual symbolic power, quality journalism added to the stock of public knowledge and contributed to dialogical urban learning. After the project ended, some reassembly of Quayside would be required.