Luck is not a zero sum game. Yes, he was partially lucky and yes, he earned every dollar. There're so many lucky people in the world and so few Allens.

I also have experience anchoring in the Caribbean, among reefs as well (abeit in a much smaller yacht, like, kind of order of magnitude smaller :-)). And no, you can't predict where your anchor chain will go, especially if your common sense contradicts what "local authority" says. Sometimes they're right (most of the time, they were born there and spent the whole life) but sometimes they are just plain drunk and do not care. Island time.