Fortune 500 rank: 457
Loss: $7.9 billion
The cell phone business has been booming, but it was a huge headache in 2008 for Freescale. The company was spun off from Motorola in 2004 and purchased by private equity for a hefty $17.6 billion in 2006, but even last year it remained dependent on its former parent's demand for chips. So when Motorola ditched its agreement to buy a set number of chips, Freescale announced it would sell the handset business, and it took $7 billion in writedowns.
Motorola wasn't the only party pulling back: Automakers, who have their own problems, also reduced their orders of microchips for cars. The debt layered on by the private equity firms is also taking its toll: Freescale said late last year it would make some interest payments by issuing more debt instead of coughing up scarce cash.