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AOL & Time Warner
Facing challenges from the growing Internet/Web and broadband industry in the late 1990s that was encroaching on its bread and butter dialup services and "walled garden" of content, on-line services provider America Online pursued a strategy of re-invention as a content and broadband giant by purchasing Time Warner in the year 2000 for a whopping $164 billion.
The merger, executed by AOL CEO Steve Case and Time Warner CEO Gerald M Levin, turned out to be a total fiasco, with the new company unable to capitalize on Time Warner's strengths. Total subscribers of AOL went from an estimated 30 million at the height of its popularity to less than just over 5 million in 2007, with no significant quarterly growth since 2002.
The company's market valuation has plunged significantly from a high of $240 billion to $1.73 billion as of February of 2012.
In 2009, shortly after appointing a new CEO, Tim Armstrong, AOL announced it would spin off Time Warner into a separate public company, ending a fruitless eight year relationship.
AOL has since gone on a New Media purchasing spree, including Patch, Techcrunch and The Huffington Post, which joins their other New Media properties such as Engdaget which it acquired as a result of its Weblogs, Inc. purchase in 2005.
The result of these New Media mergers has been something of a disaster in and of itself.
After re-organizing all of its its new media properties under one roof and appointing Arianna Huffington as its leader, TechCrunch became the subject of a highly publicized internal power struggle.
TechCrunch's founder Michael Arrington came into conflict with Huffington over journalistic ethics when he unveiled a plan, with AOL's backing, to start a venture capitalist fund to invest in the very same sort of companies which he writing for Techcrunch chronicled.
After weeks of public blog posts criticizing his employer and the media circus surrounding him, Arrington was terminated. This resulted in the departure of several members of TechCrunch's staff, including Paul Carr, one of its most popular writers, as well as the company's CEO, Heather Harde.