I would hardly call this a mistake. He choose taking smaller option package that would be more likely to be in the money than sticking with his larger option package that would only become valuable if Apple's stock skyrocketed.
There are so many variables that he doesn't have control over that if he took the bigger options he just would have been gambling. It is flawed logic to look at the outcome of an event that has so much variability and hidden factors and say that someone made the wrong choice. I would bet that if he was faced with the same situation now, knowing the outcome of this past event, he would still make the same choice because the smart choice is to not make wild gambles.