Recently, I led a project called (RE)IMAGINING Cheapside, a one-year placemaking project, sought to build inclusion and healing into a former slave auction site, adjacent to a whipping post. For centuries, enslaved African Americans, were human chattel exploited in capital transactions at Cheapside Market. Described as the epicentre of the slave trade in Kentucky, countless individuals ”granted first names only” were used to settle their owners’ debts, bequeathed to their owners’ family members, and leveraged as living mortgage payments. Notwithstanding the details of each human transaction, all enslaved African Americans were fated to forced labor, unspeakable violence, and what Langston Hughes would describe as “the dream deferred”. I designed and led a site audit, community consultations, place-based storytelling walks, a children’s inclusive-design charrette, community dinners, site specific archival research, and two witnessing circles. This process generated many strategies for making the site more inclusive (both design and social aspects). It also evolved into something none of the lead partners expected it became a living case study on healing people and places with painful histories. I’d like to share the following powerful placemaking lessons derived from this productive, and at times inspired, process: Unpack the ways fraught public spaces can be a power prompt for urban equity conversations; Using Confederate Monuments as a starting point, work with participants to develop a places of pain list; Explore how unacknowledged and/or unresolved painful histories prevent people of colour and other marginalized communities from enjoying public spaces; Highlight placemaking interventions for engaging diverse stakeholders around issues of: intergenerational trauma, emotional safety, inclusion, and healing; Guide participants through a place-based healing ritual.