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Urban form should reflect collective value for place in communities. Urban squares in particular have the potential to serve as the nucleus of communities, urban artefacts that link place to memory and heritage while serving basic needs for everyday life in the city. Civic squares, those linked to governmental institutions, have further potential to facilitate community gatherings for memorialisation, commemoration, celebration and political action. Despite these important functions and potential, the incremental planning of Brooklyn in the early nineteenth century placed little emphasis on squares of any kind, despite the community’s expressed desires. Brooklyn’s first civic square, here referred to as City Hall Square, in fact emerged in the city almost as an afterthought. Despite this lack of clear intent, this square evolved as a unique place in the urban culture of the region, simultaneously a crossroads for everyday life in the city, a commercial and cultural centre and the governmental seat and judicial centre of the city and county. The square was a seamlessly woven and connected place in the larger urban structure. While some discussions in the nineteenth and early twentieth centuries, documented in the local newspaper, provide evidence of appreciation and value for this place, others suggest a resistance to the investment of community heritage and memory as it evolved. This urban space and the larger territory around it, confronted by regional pressures for transformation in the early and mid-twentieth century, was disrupted, leaving the place diminished, no longer serving as a meaningful hub of life in the city. An examination of Brooklyn City Hall Square’s emergence and diminishment reveals a problematic treatment of this place that undermined its potential as a place for civic life, a repository of memory and heritage, but also a living nucleus of the community. It also provides insights for a conceptual framework for future reconstructions or transformations that may facilitate new civic values of place and reinvigorate this urban artefact, relinking it to both the origin of the city and the city’s heritage and memory, but also the square’s future potential as an inclusive, connected and meaningful place of community and civic spirit.