Background: In the least densely populated residential neighborhood of Chicago, deindustrial brownfields are being repurposed into sites of outdoor recreation and green spaces. This article explores the subjective experience of park development on one of these sites, focusing on how the socioeconomic contexts of the neoliberal city creates complex and ambivalent experiences of green space development. Methods: Data regarding residents' and community leaders' perceptions of park development emerge from digital and in-person participant observation, analysis of Chicago-area newspapers, and two rounds of interviews conducted in 2015–2017 and 2020–2021. Results and Discussion: Due to the continued presence of private-public partnerships and industrial activities on the Southeast Side, I find that park development on the Southeast Side of Chicago produces feelings of ambivalence rather than uninhibited enthusiasm for new parks. I suggest that this ambivalence about deindustrial land uses is characteristic of the neoliberalization of American communities. Given patterns of disinvestment and privatization in deindustrialized cities, certain land use debates summon neither passionate commitment nor vehement resistance simply because they cannot address the accrual of structural problems. Conclusion: Leveraging public–private partnerships to renovate deindustrial landscapes into sites for outdoor recreation nonetheless allows locals to emphasize why certain places near their homes are worth rendering visible once again.