Detroit is in final preparations to file for federal bankruptcy, according to a Detroit Free Press story. The paper reports, based on unnamed sources, that the filling could be as early as July 19.

The city, which is almost $20 billion in debt, is seeking Chapter Nine protection from its creditors.

The filling would be the largest municipal bankruptcy in U.S. history. Detroit still has more than 700,000 residents, though that’s less than half of its 1960s heyday.

The effort is being directed by Kevyn Orr, the emergency manager appointed by Michigan Gov. Rick Snyder in March. Snyder would have to sign off on the filing.

The filling would add another ignominious chapter to the history of Motor City.

Once one of America’s biggest and most prosperous cities, thanks to the auto industry, it is today one of the country’s most blighted, with soaring crime, decaying infrastructure and a shrinking population.