The Biggest Acquisition Failure In Recent History With so much talk about $TSLA maven Elon Musk taking over $TWTR, it’s a fun opportunity to look back at other headline-grabbing acquisitions. Acquisitions are an essential part of big business. Many of them are successful, but the ones that really stand out are those colossal failures. Let’s turn the clock back some twenty years and go down memory lane of one of the most impressively disastrous acquisitions. Back when AOL was still a thing, it spent $165 billion to acquire Time Warner. This was peak dotcom era and AOL was seeking to become a fully-rounded conglomerate—combining their internet dominance with Time Warner’s publishing, entertainment and news outlets. However, the integration caused clashes. Managerial differences amassed. Then the dotcom bubble came and caused AOL stock to plummet. The two parted ways, spinning off into separate companies. That’s the story of a $165 billion divorce.