Sale price: $165 billion
We all owe a debt of gratitude to America Online ( AOL). In its day, it was how almost all Americans discovered the Internet. And it was great and powerful in its day, until it got too big for its own good. Cue the .WAV file: "You've got hubris." In what many consider to be the worst business deal of all time, AOL -- jacked up on the dot-com bubble like a wrestler on steroids -- brokered a $165 billion deal (or, in a lack of consensus with an intensity peculiar to this case, $284 billion or any of several other valuations) to buy the traditional media giant Time Warner ( TWX). Then a funny thing happened. People stopped using modems, discovered that the Web was for more than just arguing Kirk vs. Picard in a Star Trek chat room and new, better and cheaper ISPs emerged. Worst of all, the gold rush of the dot-com era imploded. The vision of new and old media joining forces to conquer the world proved a very expensive pipe dream. The companies are now back to being separate entities, and AOL continues to seek its niche in a rapidly changing world. It still hasn't given up its media aspirations, though, and has gone on to buy sites such as the Huffington Post and build a national network of community news sites branded as Patch. -- Written by Joe Mont in Boston. >To contact the writer of this article, click here: Joe Mont. >To follow the writer on Twitter, go to http://twitter.com/josephmont. >To submit a news tip, send an email to: firstname.lastname@example.org.