13 of 20
13. Freescale Semiconductor
Freescale Semiconductor
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.

NEXT: Gannett
Last updated April 21 2009: 3:34 PM ET
Top 50 Exxon Mobil pushes Wal-Mart aside to retake the No. 1 slot this year. Which other companies made the top 50 this year? More
They're hiring! As many big companies are announcing mass layoffs, these Fortune 100 employers have at least 150 openings each. More
Best big companies to work for See the 31 companies that made both the Fortune 1000 and Best Companies to Work For lists this year. More