Abstract: This paper documents Cincinnati抯 development history since its founding, including exploitive land use patterns and unwise engineering practices that resulted in long-term if not perpetual financial responsibilities for the city and its residents. It highlights steps the city has taken over the last 40 years to try to mitigate slope instability, and it suggests additional measures the city can take to be more proactive concerning future hillside development. The paper also documents the work of The Hillside Trust, a non-profit organization created in 1976 to advocate for the thoughtful use and preservation of the Cincinnati region抯 hillsides.