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Gentrification and its displacement of residents in poverty and racially minoritized communities have sparked battles over school choice, school belonging, and the right to space (Davis & Oakley, 2013). However, we need to learn more about how gentrification and neoliberal education restructuring (Lipman, 2011) contribute to the displacement and weakening of community-based educational spaces (CBES) (e.g., afterschool programs, youth centers) and those that uphold these spaces — youth workers. This paper asks: How and in what ways are community-based educational spaces shaped by city change? How and in what ways do gentrification, education restructuring, and housing insecurity inform youth workers’ professional stability? How do youth workers understand and respond to gentrification and education restructuring? Findings reveal that parents are displaced by gentrification and forced to live hours from their jobs, leading to long commutes and insufficient rest for students. Aligned with growing work on the precarious lives of youth workers, findings also show that youth workers are housing-insecure. Finally, findings show that a collaborative, multi-sector community-based resistance among school and community-based education spaces, community health partners, employment, and housing activists generates a more sustainable fight against the threat of gentrification and housing insecurity.