2 of 20
2. Fannie Mae
Fannie Mae
Fortune 500 rank: 112
Loss: $58.7 billion

It wasn't long ago that business was easy for a quasi-governmental entity with a mandate to expand home ownership. Washington-based Fannie borrowed money at low rates, then used it to buy or guarantee roughly 20 million mortgages. A big lobbying budget meant execs were welcome in just about any congressional office.

But these days, Fannie is more like the government's punching bag. As the delinquency rate on the single-family home loans it guarantees more than doubled last year, the company was taken over by Treasury, which is now using it to absorb an endless stream of housing market losses. Last year Fannie lost a staggering $30 billion on its mortgage guarantees alone. By now, execs will be lucky to get a congressional Christmas card.

NEXT: Freddie Mac
Last updated April 21 2009: 3:34 PM ET
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