68. The Historical Merger of AOL and Time Warner

Year: 2000

Location: New York City, New York (AOL HQ)

Company: AOL, Time Warner

Estimated Damage Value: $98.7 billion*

In 2000, in a landmark event marking the peak of the dot-com bubble, AOL, headquartered in New York, announced the acquisition of Time Warner for $182 billion. This event registered as the largest merger in corporate history, valued at an estimated loss of $98.7 billion, establishing a cautionary tale in corporate America.

The merger between AOL and Time Warner is a textbook example of a failure due to mismatched expectations, often cited as a ‘corporate culture clash’. Despite visions of gaining vast numbers of cable customers and subscribers, both companies fell short of their ambitious goals.