GM's Rick Wagoner bought low, then bought out.

In 2000, General Motors paid $2.4 billion for 20 percent of then-struggling automaker Fiat. It looked like a good deal at the time, but someone should’ve read the fine print.

By 2005, the Italian company was in even worse shape. With mounting debt, it was threatening to execute a "put option" in the contract which would have forced GM purchase the rest of the company, and all of the problems that went along with it.

Rather than absorb the company and add to its own problems, Wagoner decided to bite the bullet and pony up another $2 billion in a settlement that let it walk away from the deal with virtually nothing to show for it.

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