2. Hewlett-Packard & Autonomy
Hewlett-Packard CEO Leo Apotheker is not immune to bad deals himself. In October of 2011, he brokered the deal to acquire British software maker Autonomy Corporation for $12 billion. Hewlett CEO Apotheker purchased Autonomy to help move the company away from hardware and into the more lucrative software side of corporate spending. Fast-forward, when Apotheker was replaced by Meg Whitman, the current Hewlett CEO, irregularities were uncovered at Automomy. Eleven months after the purchase, Hewlett took an $8.8 billion charge due to "accounting errors" that resulted in Autonomy revenue being overstated by 54%.