Year: 2008

Buyout Offer: $44.6 billion from Microsoft

What happened: Before Microsoft launched its Bing search engine, the giant from Redmond, Wash. wanted to buy the ailing search company turned web portal Yahoo! In an unsolicited bid, Microsoft offered to buy the company for $44.6 billion. Yahoo! turned it down saying that it "substantially undervalues" the company. Two years later, after creating its own search engine, Microsoft struck a 10-year deal with Yahoo! that would have Bing powering Yahoo!'s search. Funny how things work out.