Corporate reversal: AOL Time Warner Merger

The blunder: In a $164 billion deal during the 2000 dotcom frenzy, old line media company Time Warner merged with portal AOL—at one point the door to the Internet for 30 million consumers. The idea was to cross-market Time Warner content, like movies and magazines, to AOL subscribers, and deliver it all using Time Warner’s cable pipes. The timing was terrible—just months before the bursting of the dotcom bubble. Time Warner veterans dragged their feet about working with AOL, and the expected synergies never materialized.

What might have been: Time Warner and Yahoo were discussing a merger in 1999. Yahoo decided not to pursue it.

The reversal: In May 2009, Time Warner said it would spin off AOL . The divorce became official in December that year.(Reuters)