Will AOL's new merger go better than the last one?

The shadow of Time Warner hangs over AOL's deal with Verizon

AOL Time Warner

For anyone looking for a takeaway from Verizon's surprise move, announced on Tuesday, to buy AOL, the lesson might be this: Sometimes discretion is the better part of valor.

The deal will go down for the relatively modest sum of $4.4 billion, and should be completed sometime in the summer, assuming all is cool with federal regulators. But compare that price tag to what happened 15 years ago this January, when AOL — then at the peak of its powers — bought Time Warner for a staggering $165 billion, creating a combined company valued at $350 billion. The word "transformational" was bandied about so much to describe the deal that it's now considered something of a wry joke. It remains one of the largest mergers — if not the largest merger — in corporate history.

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Jeff Spross

Jeff Spross was the economics and business correspondent at TheWeek.com. He was previously a reporter at ThinkProgress.