“It was the best of times, it was the worst of times” could easily capture the “simultaneous utopia and dystopia”(1) of today’s digital landscape. Smart Cities, cities that employ modern sensor, networking, and big data technologies to “manage and control urban environments in real-time”(2) are quickly evolving from the theoretical musings of technologists and sci-fi writers to reality. Yet they have been greeted with a mix of public optimism and trepidation. The opportunity for digital transformation is great, but so are the privacy and other risks in the absence of robust governance structures and thoughtful policy decisions. While privacy laws have the potential to provide a helpful framework for grappling with these issues, they need to be understood in their broader social context. Smart cities are, after all, populated by (smart) people who are concerned about a range of social issues. Such is one of the valuable lessons to be gleaned from Sidewalk Labs’ 2017 entry and May 2020 departure from Toronto’s Quayside Smart City initiative. Toronto’s experience stands in contrast to that of the ongoing Smarter London Together initiative (Smart London), which launched in 2018. In this article, we examine the two initiatives through a privacy lens but with a view to broader issues privacy professionals should consider when advising on Smart City initiatives.