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5. Citigroup
Citigroup
Fortune 500 rank: 12
Loss: $27.7 billion

The unwieldy banking supermarket built by Sandy Weill finally came undone, losing money in every quarter of 2008. The headliner was a $14 billion loss in subprime mortgages, but the bank also took a $10 billion writedown on the value of companies it acquired during its long corporate shopping spree. CEO Vikram Pandit has begun the process of divorcing Citi's bank and brokerage businesses by placing Smith Barney in a joint venture with Morgan Stanley.

In February 2009, the government took took up to a 36%stake in exchange for its third capital infusion and a big asset guarantee. And in April, Citi surprised Wall Street with its first quarterly profit in more than a year, helped by strength within its investment banking division.

NEXT: Merrill Lynch
Last updated April 21 2009: 3:34 PM ET
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