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Yahoo turns down payday
Yahoo turns down payday
Outgoing Yahoo CEO Jerry Yang
If Microsoft's offer for Yahoo was wrong-headed, Yahoo's opposition to it was downright bone-headed. It took until July, when Microsoft finally throws up its hands and walks away, for Yahoo CEO Jerry Yang to fumble a deal that would have rewarded shareholders with a payday that was three times what Yahoo shares were fetching at year-end.

Along the way, Yahoo flirts with Google - only to see any potential deal scuttled by antitrust regulators. As 2009 approaches, Yahoo's chances of turning itself around look slim. -- By Adam Lashinsky, Fortune editor at large

What do you think was the year's Dumbest Moment in Business?Join the discussion now.

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