Abstract: Of the various facets of Smart City design, the one that receives the most attention is the technological. The one that receives the least is that of physical design. From a city-making point of view, the reality should really be the exact inverse. Successful smart cities must fundamentally first uphold the basic conditions that have always characterized great cities. They must be the tablet upon which the richness and complexity of human life can be written and rewritten a thousand times over. Intelligent digital networks in cities are of course now essential; their incorporation should be a given, and from there, focus should be on excellence of actual urban place-making. Toronto is perhaps the most interesting test-bed for Smart City ideas in the world right now, here we look at two case studies by Sasaki in the Metro region.