4. Energy Future Holdings
Fortune 500 rank: 292
2010 loss: $2.8 billion
This Dallas, TX-based electric utility company formally known as TXU Corp. was taken private in 2007 and has since been saddled with debt. The $45 billion leveraged buyout remains the biggest recorded in U.S. history and was one of the last big private equity deals before the financial crisis.
Fast-forward to today and the deal has continued to haunt Energy Future Holdings. Texas's largest power provider saw a loss of $2.8 billion in 2010, partly reflecting lower prices for natural gas and wholesale power.
NEXT: 5. Bank of America Corp.
Last updated May 05 2011: 3:06 PM ET
