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How can we transform downtowns through civic imagination and engagement? Urban downtowns across the US are falling on hard times: empty shopfronts, vacant offices, and soaring rents. These tough times provide the basis for reimagination and renewal as the world around us enters a new era. Could we face these urban challenges head-on and consider this downfall an opportunity for cities and citizens to flourish for a more sustainable future? What opportunities for fresh imagination and growth does it create? How can emergent technologies like AI support this as a civic practice?