#2 – Apple Newton
Newton was a platform for the MessagePad, a Personal Digital Assistant (PDA) released by Apple Computer in 1993. The PDA category didn’t even exist until Apple brought Newton and the MessagePad to market. It provided applications such as Notes, Names and a Calculator, and it was the first device capable of handwriting recognition. However, it proved to be too big and bulky to be used as a pocket PDA. Attempts to make it smaller (by iPhone designer Jonny Ive) failed, and Apple discontinued the project in February 1998. It was the failure of this project that prompted the Apple Board of Directors to fire their CEO, and bring back Steve Jobs.