This thesis is interested in understanding the multiple expressions of speculative housing ownership under a right-sizing policy-planning experiment, which was designed to resolve Detroit’s fiscal crisis after decades of anti-radical politics and neoliberal retrenchment. Understanding that question would be incomplete without an inquiry into how the city became fiscally constrained and why the city suffered from urban decline for more than a half century, where we can begin to discern the consequences of such material deterioration today. Alongside an analysis of neighborhood-scale socioeconomic variables, I analyze data on demolition, building permits, blight violations, vacancy, and housing speculation in Detroit from 2015 to 2023 to investigate the relationship between housing speculation and right-sizing. Through a cluster analysis of this data, I demonstrate the different relationships between these indicators, detailing broader processes of uneven development and their manifestation as differing strategies of speculative investment taking place in Detroit, which are ultimately deployed as subterfuge to rebuild and hegemonize Detroit according to neoliberal market rationalities.