You read a lot about failed nation-states these days - e.g., the argument that there's not a country in Africa which "works," as measured by fairly low-level, First World 20th century expectations - but you don't read a lot about failed cities within the U.S.
Maybe that's because no one drawing a paycheck in the domestic "future-of-urbanism" business wants to admit to failure. There's an exception which, you might say, proves the rule: the city of New Haven, Connecticut, as described in the pages of City: The End of Urbanism written by Douglas Rae.
In some 500 pages of charts and text he documents the founding, rise to pre-eminence, decline, and near-collapse of a place which started out as eight squares of buildings around a central common in a 17th century wilderness; rose to regional industrial dominance in the late 19th century; and by the 1920's was beginning to experience serious flight of exactly those middle- and upper-class populations without which urban centers can survive only by constant outside subsidy.
Rae is a member of the professoriat of Yale University, which was a minor contributor to New Haven's rise from minor ag-service and colony-governance center to major manufacturing complex during the first three centuries of its history.
Now all that manufacturing industry is gone. Yale is by default the city's single largest employer and (intellectual) wealth-creator, and he writes with typical academic urban-advocate nostalgia and admiration for what he calls a "sidewalk republic," in which wage-earning factory workers walked back and forth to and from their mill jobs, there were tiny little A&P grocery stores (most in the 1,000 square feet-size range) every few blocks in residential neighborhoods of fairly-tightly packed single- and multi-family housing, and the locals embraced their fraternal organizations, churches, and neighborhood parks for Saturday afternoon outings.