It was, and still is, the largest merger in history. In 2000, AOL and Time Warner merged in a business deal valued at $165 billion — about $245 billion today. The deal itself took one year to be approved by regulatory entities and became the biggest disaster in business history. For starters, the two companies hated one another.
“I saw AOL in a much less favorable light [than Time Warner], much more opportunistic, made up of folks who were really trying to merely exploit the market they were in as opposed to developing something that was enduring, and I was very leery about this deal,” Timothy Boggs, then a Time Warner senior VP, told the New York Times.
The dot-com bubble began to burst in mid-2000, slowing financial forecasts for AOL. As the bubble burst in 2001, stockholders pulled out. Later, it would be discovered that AOL had been inflating its advertising revenue by over $1 billion, drawing the ire of the S.E.C. and Department of Justice, resulting in $510 million in fines. By 2009, AOL and Time Warner parted ways. May the 2020s bring us even more schadenfreude.