The 21st century dawned with news that two media megaliths, AOL and Time Warner, were to merge. Critics howled that the vast tentacles of a combined AOL-TW would subsume us all. Today, Time Warner confirmed it's spinning off AOL, ending a business saga that defined whatever you're calling the 2000s.

In retrospect, AOL's deal to acquire — and then be run by — Time Warner marked the end of a century when old media conglomerates were at their peak. The merger, valued at $182 billion when it was announced, was the largest in U.S. history. It is also arguably the most disastrous in history. The combined value of the two companies — both inflated by the dot-com bubble — was $350 billion. Today, before the spin-off goes through, the whole shebang sports a market cap of just under $28 billion.

Now that the struggling old media company is parting ways with its fast-shrinking internet toy, the media's hand-wringing over the deal nine years ago looks absurdly hubristic in retrospect.

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Here are some quotes from early 2000, after the deal was announced (and about a year before it was consummated):

  • New York Times: A "merger of tree-snapping behemoths... the Godzilla of the Internet... wed the King Kong of content. It is a natural time for the other denizens of the jungle to wonder what the future will hold for the colossal couple and the world they inhabit."
  • USA Today: "It's one of those rare events that seems to change the world overnight... We're shocked... "
  • Newsweek: "AOL Time Warner will be unchallenged in its online customer base and hold vast cable-television assets."
  • Regional telco SBC Communications, as quoted in CBS Marketwatch: "The merger will establish, through a web of equity and contractual interests, one interlocking conglomerate with control over both the high-speed pipes consumers use to connect to the Internet and the content they access once they're online."
  • Salon, April Fool's Day: "AOL Time Warner announced Friday that it had acquired France."

There were some pessimists; a columnist named Paul Krugman wrote that only time would tell about the wisdom of the deal, and that it's possible " some big businessmen have just made a very big mistake."

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Instead of fearsome tentacles everywhere, Time Warner is now left with the old-line business it was in before the 2000 deal. Except those assets — cable networks, a movie studio, magazines — now face more obstacles to growth than they did eight years ago.

AOL chief Tim Armstrong, the former Google sales chief, finally has his own company to run; it remains to be seen whether he can reverse AOL's steadily declining advertising revenues. But it's Time Warner that's left with the tougher job: Proving media conglomerates can still post impressive growth amid the rise of online media consumption.