Revenues plunged due to lower prices
2. Energy Future Holdings. Bankrupt April 29, 2014. Assets $36.4 billion
Energy Future Holdings became the largest power producer in Texas in 2007 after a $45 billion buyout of TXU Corp. But the company struggled under the weight of $40 billion in debt after revenues plunged due to lower prices for natural gas and electricity. Energy Future Holdings was broken up in April under the terms of a restructuring deal.
3. Pacific Gas & Electric Company. Bankrupt April 6, 2001. Assets $36.1 billion
California's largest publicly-owned utility went bust after deregulation led the company to incur billions in debt. After selling its gas power plants, the company had to buy power from other energy companies. Buying at fluctuating prices and selling at fixed prices led to losses and eventual bankruptcy. But according to Time, wholesale prices eventually dropped, and the day the company emerged from bankruptcy in 2004, its stock was worth three times as much as when it filed for protection.
4. Texaco. Bankrupt April 12, 1987. Assets $34.9 billion
Texaco started out in 1901 as the Texas Fuel Company and was independent for 100 years before merging with Chevron in 2001. However, in the 1980s, Texaco became embroiled in a legal battle with Pennzoil, and ended up owing the company $10.5 billion. That led to Texaco filing for bankruptcy, which at the time, was the largest in U.S. history.