Here are some of the largest municipal bankruptcies in America, ranked by the amount of debt:
City of Detroit, Michigan (2013) - Debt: $18.5 billion
Jefferson County, Alabama (2011) - Debt: $4.2 billion
Orange County, California (1994) - Debt: $1.7 billion
Stockton, California (2012) - Debt: $1 billion
San Bernardino, California (2012) - Debt: $900 million
Harrisburg, Pennsylvania (2011) - Debt: $600 million
Central Falls, Rhode Island (2011) - Debt: $21 million
It is worth noting that municipal bankruptcies are relatively rare, and most municipalities are able to manage their finances without declaring bankruptcy.
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