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HP & Autonomy
In addition to the scuttling of the TouchPad and the WebOS/Palm division at HP, Leo Apotheker's very short term as HP Chairman and CEO will be always known for the company's $11.1 billion acquisition of Autonomy, a European maker of unstructured data analytics software.
At the time the purchase occured many industry observers were keen on figuring out what HP would do with the technology after the acquisition, and well over a year later HP has still not effectively communicated how it fits in to its overall enterprise software strategy.
But the real bombshell came in 2012 when the company announced that after an internal investigation, HP had discovered there were severe accounting improprieties at Autonomy during its acquisition and would have to write down almost a $9 billion loss, sending the company's stock into a tailspin.
This alone probably makes the Autonomy purchase by HP the most infamous and wasteful cash spend for a software assset of all time.