5. Microsoft and aQuantive: This acquisition went down just like the other buy Microsoft made of Danger—the company’s executives left two years after the deal closed, and the acquisition of $6 billion never really worked out.

4. Yahoo bought Broadcast.com for $5 billion: Back in 1999, in the middle of the dotcom boom, Yahoo gave the CEO of Broadcast.com a whopping $5 billion for the acquisition—and Cuban went out to buy out an American Basketball team (the Mavericks) for the money. The incident was all over the news, and implanted itself deep in the ‘national landscape’, as according to the Business Insider report.