The short answer is that he doesn't know what he is doing. The $100m loss is way too much, and I believe he is the worst loser in the history of trading. I wonder how greedy and emotional he was to take such a huge risk in trading.
For me, his greediness isn't the main problem. His issue is that he hunts his primary choice without making any prior decision, even if he sees that things are not going as planned. It's as if he placed an order and forgot about it, which isn't the case here. However, his obsession with closing his trades at the levels he was set from the start drove him to a great loss. As for being the worst loser in history, I doubt that he is. Many others lost huge like him but are not known since they don't post their trades. Of course, the same goes for winners.