An internationally celebrated icon of community planning and grassroots activism, the late American urbanist Jane Jacobs is frequently reduced to a caricature of polite, all-purpose sentiments which obfuscate both the complexity and the political specificity of her work. In the first portion of this paper, I examine the popular representation of Jacobs by prominent urban nonprofits, as well as the ambiguity of her intellectual legacy in both urban scholarship and in recent media about her career. Highlighting Jacobs’s warm reception among libertarian thinkers, I devote the second portion of this paper to exploring the intellectual affinity between Jacobs and the famed Austrian economist Friedrich Hayek. Demonstrating their key points of convergence on mat- ters of social policy, governance, and expertise in relation to watershed moments in planning history, I conclude with an analysis of Jacobs’s little-discussed writing on American public housing, noting the various parallels between her argumentation and the radical reformation of American housing policy during the turn to “advanced liberalism” which occurred in the decades following the publication of her classic 1961 book The Death and Life of Great American Cities.