Times are tough in Motor City. In the largest municipal bankruptcy filing in U.S. history, the emergency manager of Detroit asked a federal judge for permission to put the city into Chapter 9 bankruptcy protection on Thursday afternoon. Gov. Rick Snyder said in a letter authorizing the filing that he understood “many will see this as a low point in the city’s history.” Adding: “If so, I think it will also be the foundation of the city’s future." Detroit has been struggling for years, with a deficit that has hit $18 billion, while losing around a quarter-million residents in the past decade. If the filing is approved, the city will be allowed to liquidate assets to repay creditors and city pensioners who’ve lost money from bad bond investments and unpaid contracts.