This was a banner decade for big bankruptcy.

Of the 20 largest corporate bankruptcy filings in history, all but three of them occurred in the last decade.

The 2000s featured three businesses with more than $100 billion in assets filing for bankruptcy. All the companies in the list here held more than $30 billion in assets.

Combined size of the biggest companies filing bankruptcy this decade: $1.5 trillion. That would make them the 10th richest country in the world with a greater GDP than Canada, India, Mexico, Australia and most of Europe.

The Biggest Business Bankruptcies of Decade

Pacific Gas and Electric: $36.1 billion
April 2001
The story: After California deregulated the state’s energy industry, the state entered an energy crisis as companies couldn’t sell energy for more than they paid for it. Pacific Gas and Electric began taking on debt as Californians experienced rolling blackouts across the state. The company was bailed out by the state government, which provided cash for the company during its reorganization. While this move saved the company, it did add to the long list of budget problems still plaguing the state.

Enron: $65.5 billion
December 2001
The story: At one time Enron was one of the world’s leading energy companies, a blue-chip stock, and regularly lauded by the business world. But all of that began to unravel in the late 1990s as a massive accounting fraud and insider trading scandal was unveiled. Enron had been hiding losses in offshore companies for years, and falsely inflating their stock. When this knowledge became public, the company was forced to file what was then the largest bankruptcy filing in history.

WorldCom: $107 billion
July 2002
The story: In 2002, WorldCom was the second largest long distance phone company, but nearly $4 billion in billing fraud led to what was then the largest bankruptcy in US history. Following bankruptcy, the company changed its name to MCI and was later purchased by Verizon in 2005.

Conseco: $61.4 billion
December 2002
The story: A large insurance company based in Indiana, Conseco launched a financial arm of the company in the late 1990s with the purchase of a leader in the mobile home financing industry. The move proved costly, and led to bankruptcy reorganization early this decade. The plan worked in the short-term, and Conseco emerged ready to do business again, although late this year new financial concerns may be appearing.

Lehman Brothers: $691 billion
September 2008
The story: The Lehman Brothers bankruptcy filing is far and away the largest by an American corporation in history. Founded more than 150 year ago, it eventually grew into the third largest brokerage firm in the country, and the largest mortgage underwriter. The firm made a fortune during the housing boom earlier this decade, but was at the center of the subprime mortgage collapse. After a frantic search for buyers that turned up empty, and no help from the US government, Lehman collapsed. The company has continued to be in the news as bonus paychecks for executives at the firm have triggered outrage and scrutiny.

Washington Mutual: $327.0 billion
September 2008
The story: Another victim subprime mortgage victim in September of 2008, WaMu burst as quickly as the housing bubble that helped it grow into one of the largest banks in the country. But after the Lehman Brothers collapse, customers made massive withdrawals at WaMu for fears it would soon fold, too. The government quickly took over, and forced a sale to JP Morgan Chase, marking WaMu’s fate as the largest bank failure ever in the US.

Chrysler: $39.3 billion
April 2009
The story: Though not the first car company hit by weak sales and high loses, Chrysler was the first American automaker to file bankruptcy since Studebaker in 1933. The company was reorganized through bankruptcy and government invervention that led part of the company to be acquired by the United Auto Workers Union and another portion to be sold to Italian company Fiat.

Thornburg Mortgage: $36.56 billion
May 2009
The story: Thornburg specialized in “jumbo” adjustable rate mortgages: Those worth more than $400,000. But, as the value of these mortgages fell along with mortgage values across the board in the middle part of this decade, Thornburg was one of many mortgage companies with a bankruptcy case in the $30 billion range. Although the company officially entered Chapter 11, it sold its assets and was officially closed.

General Motors Corporation: $91 billion
June 2009
The story: The beleaguered car company was forced into bankruptcy earlier this year as the federal government poured in billions of dollars to keep the company afloat. The auto-maker’s executives had asked the government for financial help and declared they were close to insolvency. But in exchange for financial support, the feds wanted GM to be reorganized in Chapter 11. The bankruptcy led to the closing of brands Saturn and Pontiac; Hummer was sold to a Chinese company; and the future of Saab is still up in the air.

CIT Group: $71 billion
November 2009
The story: CIT Group is one of the largest commercial lenders in the country, specializing in loans to small and mid-size businesses. But they lost $3 billion over two years, and continued to struggle despite receiving billions in cash and loans from the federal government and other lenders. Despite plans to emerge quickly, their bankruptcy raises questions on how small businesses, including 2,000 vendors supplying goods to 300,000 stores, will be affected.