"Presumably he thought he could get away with it because he wasn't named or being actively monitored."
On the other hand, I'd not be surprised to learn that ANY large transaction during a "blackout period" is looked at more closely than usual. After all, look how many insider traders have been caught getting others to do the trades for them, eg friends and/or family. I'd imagine even with a company the size and value of Apple, $10m trades don't happen all that frequently, especially close to an earnings/performance announcement.