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Detroit

Year of filing: 2013

With its bankruptcy filing, the city of Detroit has entered uncharted territory. It's a place that no major U.S. city has ever gone—but that could change.

Despite the uncertainties surrounding what's expected to be a hard-fought legal battle, the outcome promises to inflict more pain on Detroit's already-beleaguered residents, businesses, creditors, investors and city workers, whose pension plans may now be invalidated.

Jeff Kowalsky | Bloomberg | Getty Images