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CALIFORNIA CHEDDA' Michael Huffington, pictured with then-wife Arianna (Photo: Getty Images)

A House seat isn't usually all that expensive. It was just $545,000 in 1993, Fortune magazine estimated, not long after Michael Huffington spent an impressive $5.6 million in a bid to buy his own. Huffington, a Texas transplant to the central coast of California, was then married to Greek-born columnist Arianna Huffington—at the time she was also a right-winger. Soon after buying the most expensive congressional seat in history, Huffington launched the most expensive senatorial campaign in history.

Huffington spent at least $30 million—about a third of his net worth—against incumbent democrat Diane Feinstein, who had filled the seat via a special election in 1992. Feinstein told the New York Times that she sensed trouble when she saw a one-minute Huffington ad during the winter Olympics in February—more than a little early. She wound up funding some portion of her own $14 million campaign, and edged out Huffington by a scant 1.9 percent. At the end of it all, Huffington, who ran as an upper-management conservative, didn't get a tremendous return on his investment.

In the years that followed Mike's defeat, the Huffingtons both transformed: Arianna into the leftie we know and love, and who founded the Huffington Post, and Michael into an out-of-the-closet bisexual. In an Esquire profile, he said he never wanted to win the election and he was glad he'd lost. Arianna ran for governor in California's 2003 recall election. Michael supported Arnold Schwarzenegger.

Total Amount Spent: $30 million
Cost Per Vote: $7.86