Boomerang entrepreneurs (practicing and nascent entrepreneurs who return to their declining home cities after years away) may especially be an answer to the brain drain, suppressed innovation, and often tepid entrepreneurial ecosystem condition that plague declining cities such as U.S. Rust Belt cities. This conceptual article addresses how the declining home city’s place image might inform and promote a boomerang entrepreneur’s return migration and venturing decisions and with what implications for the place’s entrepreneurial ecosystem. Even given homesickness, this kind of return migration is unlikely unless prospective boomerang entrepreneurs revise their place images of their old hometowns. We conceptually develop and support propositions on the relationships between place image and brain drain, between affect and both place image revision and entrepreneurial intentions, and between place image revision and both return migration intentions and entrepreneurial opportunity recognition. We also discuss implications for microfoundations of entrepreneurial ecosystems in declining cities, place branding that can encourage boomerang entrepreneurs’ place image revision and return migration to the declining home city, and related research data collection.