Detroit filed the largest municipal bankruptcy in U.S. history Thursday, marking a new low in a long decline that has left the American automaking capital bleeding residents and revenue, while rendering city services a mess.

The Motor City, which was the nation's fourth-largest in the 1950s with nearly 2 million inhabitants, has seen its population plummet to 700,000 as residents fled increasing crime and deteriorating basic services, taking their tax dollars with them.

As Detroit faced an estimated debt of $19 billion, the state in March appointed an emergency manager vested with extraordinary powers to rewrite contracts and liquidate some of the city's most valuable assets.