Detroit has filed for bankruptcy, making it the largest municipality in the history of the United States to do so, the Associated Press reports.

Kevyn Orr, the state-appointed emergency manager for the city, has asked a federal judge to place the city into Chapter 9 bankruptcy protection.

Orr was appointed by Michigan’s Republican governor, Rick Snyder, back in March, a move that placed the city under his management. Orr previously worked on Chrysler’s 2009 bankruptcy.