This paper uses experiences from a decade-long community-based research project in the Pilsen neighborhood of Chicago, a Mexican-American neighborhood whose residents are both experiencing and resisting gentrification, to show how displacements and contestations evolve in conversation with each other in an iterative process we could call “actually existing” gentrifications. I analyze a series of “moments” in 13 years of research in Pilsen to illustrate the constantly shifting terrain of gentrification politics, covering not just housing affordability, but the nature of identity, democracy, and belonging. As communities develop resistance strategies to gentrification, so too do city planners, policy makers and developers adapt to these community strategies to reframe their vision of the community. In highlighting both the success of community resistance in mitigating some of the worst effects of gentrification and the cooptation of some of these same strategies in the reframing of gentrification, my goal is to show that gentrification is rarely ever done or complete but continuously enacted and resisted, challenging the idea that gentrification is somehow inevitable.