AOL’s 2000 buyout of Time Warner for $164 billion easily takes the cake as the worst deal of the decade. Inked at the height of the dotcom bubble and the pinnacle of AOL’s business, this attempted marriage of content and distribution fell on its face.
“It’s the mother of all failed mergers. It was the iconic deal from hell,” said Robert Bruner, who wrote Deals From Hell.
By trying to focus on both content and distribution, AOL Time Warner ended up not being very good at either. AOL went from having 30 million members at its peak in 2002 to just six million today. At the time, the companies said the deal would create a company valued at $350 billion. Nine years later and Time Warner is worth barely $37 billion. (REUTERS/Mike Segar)