Biggest Acquisition Failures Of All Time

But in the last decade, a dizzying series of scandals and a rapid churn of chief executive officers have left Hewlett-Packard wondering where it went wrong. One instance would be the $10.2 billion acquisition of Autonomy, a U.K.-based enterprise software company.

Autonomy's absorption into its parent company was uneventful. However, after a few months, HP management argued that Autonomy was overpriced. CEO Meg Whitman said Autonomy was "smaller and less profitable than we had thought," leaving open the question of how convincingly a company could overstate its size to a sophisticated bidder. Legal threats notwithstanding – and as you can imagine, Autonomy's founders said they didn't do anything wrong and that HP was just covering up its own ineptitude – Hewlett-Packard ending up taking a gargantuan $8.8 billion write-off. The transition into a software company was indeed a rocky one.

Before Chrysler became a privately held company, it was a publicly held giant of American industry. It was a consistent third place among the three Detroit auto manufacturers, but still among the largest corporations in the country in absolute terms.

In 1998, it became the subject of an infamous international acquisition. That year, German carmaker Daimler, maker of Mercedes-Benz, merged with Chrysler via a $39 billion stock swap. Shortly thereafter, disgruntled Chrysler shareholders filed a class-action suit. It cost DaimlerChrysler's German CEO his job. By 2006, Daimler was actively looking to rid itself of an expensive tentacle.

The Chrysler division was eventually sold to a private equity firm, Cerberus Capital Management, in 2007. Officially, it was a $7.4 billion exchange. Two years later, Chrysler's new owners filed for bankruptcy and were rewarded with a taxpayer-funded bailout.