Where did he get his rationalist training then? If he's in a rational community that's not LW, I'd consider him a reason to check that community out.
He's a smart guy who's spent a lot of time around other smart people.
Around here people tend to overestimate how much "rationality training" lesswrong provides and underestimate the level of rationality present in the rest of society.
http://mentalfloss.com/article/54853/our-interview-jeopardy-champion-arthur-chu
I'm not sure I've ever seen such a compelling "rationality success story". There's so much that's right here.
The part that really grabs me about this is that there's no indication that his success has depended on "natural" skill or talent. And none of the strategies he's using are from novel research. He just studied the "literature" and took the results seriously. He didn't arbitrarily deviate from the known best practice based on aesthetics or intuition. And he kept a simple, single-minded focus on his goal. No lost purposes here --- just win as much money as possible, bank the winnings, and use it to self-insure. It's rationality-as-winning, plain and simple.