The prevailing argument for school choice in metropolitan cities has been that children from economically disadvantaged communities need opportunities to access better quality schools than the traditional public schools assigned to them based on their address. However, as these cities experience gentrification, more economically advantaged parents are taking advantage of school choice policies for their children -- despite already living in the catchment zones for highly desirable traditional public schools. This study explores the intersection of community and school gentrification and the motivations for supporting and participating in the school choice process for parents in Washington, D.C., a highly gentrified city with a robust school choice landscape. Leveraging a relatively robust school choice system, the author interviewed 25 professional-class, low-income, and working-class parents in Washington, D.C. who completed applications for the citywide school lottery. The findings show that parents have vastly different priorities when choosing schools, depending largely on race, class, and whether they are a gentrifier or native Washingtonian. The findings reveal contradictions between the stated values and the actions among White professional-class parents, a pursuit of equality of conditions for low-income and working-class Black parents, and tensions between gentrifying and native parents in communities as gentrification changes the complexion and culture of schools.