Date: Jan. 10, 2000

Acquired for: $162 Billion

The idea of merging one of the biggest digital content providers with the leading Web portal at the time seemed like the perfect marriage. Well, as we witnessed, the matrimony between AOL and Time Warner would turn out to become arguably the worst corporate takeover ever. Rumors of TimeWarner execs throwing shade toward its inheritor, along with AOL’s refusal to upgrade from its dial-up service were cited as primary reasons for the disastrous acquisition. Throw the dot-com bust into the equation and you have a tech marriage that was destined for massive failure. If there was one lesson to be learned here, it was how not to run a multi-billion-dollar company into the ground.