2. Failure to buy Sun Microsystems, 2009

The tech industry today is driven not be ceaseless innovation, but rather stringent litigation. The world's largest mobile handset makers and software companies are currently embroiled in a massive lawsuit over patents and copyright infringement. In 2009, Oracle purchased Sun for $7.4 billion. Along with the company came the rights to Java, a technology used heavily in a number of devices and software including Google's Android. Oracle immediately took Google to court to siphon out some dough for the use of its technology. If Oracle wins it could get more way more than $7.4 billion out of Google…