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6. Western Refining
6. Western Refining
Fortune 500 rank: 330
2009 revenue: $6.8 billion
2009 total shareholder return: -39.3%

It's been a long road down for Western Refining, whose stock peaked in the heady days of the summer of 2007, when both crude oil and gasoline prices soared. Both eventually fell when the weak economy suppressed demand.

But the cost of crude bounced back faster than the price at the gas pump -- squashing margins for refiners. Western Refining issued 20 million new shares in June, a move that spurred its stock to fall further.

NEXT: 7. Winn-Dixie Stores

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Last updated April 15 2010: 7:08 AM ET
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