Launch date: 1987
Fatal flaw(s): Sub-par operating system,
Considered by many to be Apple's first tablet, the Newton was one of the first personal digital assistants to hit the market. The brainchild and personal interest of then CEO John Sculley, it was ate up about $100 million during the course of its creation. While the Newton Message Pads didn't do well commercially, the eMate, a low-powered laptop running the Newton OS aimed at the education market, managed to move a few units. None of that mattered, however, when Steve Jobs was brought back to the company. He promptly cancelled the program.
Fun fact: Two Newton developers went on to start Pixo, the company that wound up developing the software that powered the first iPod.