Once known as the “Paris of the West” and home to America’s bustling auto industry, Detroit filed for bankruptcy after fighting steady decline for half a century.

A man walks past graffiti in Detroit. The city is eligible for the biggest municipal bankruptcy in U.S. history because it is broke and negotiations with its thousands of creditors were unfeasible, a federal judge said on Tuesday. The wide-ranging ruling also said the city could cut retiree pensions. Joshua Lott/Reuters