With the concept of the “embedded artist,” Frances Whitehead developed urban design projects of varying scales, generating a series of linked civic initiatives that model a whole-systems, place-based approach. Artists were “embedded” in municipal workgroups to bring new perspectives to the daily work of the city, and artistic research and working methods were allowed to operate within and alongside the highly structured public planning processes. The chapter focuses on the cases of “Slow Cleanup” (Chicago, 2008–2012), the “606” (Chicago (2012–2016), “Diaspore” (Lima, Peru, 2009–2012), and Fruit Futures Initiative Gary (Gary, Indiana, since 2015).