> What are the first principles here?

One of his first principles might have been (example):

"Leaks really work well. I leaked some stuff, it got me good results, and so logically this path is open to me for problem-solving."

This is how subjective logic works for millions of people every day.

Obviously to you and others, if you don't combine that with some wisdom and foresight derived from broader knowledge on the context in question, it might backfire.

But what happens next is probably this: He'll stay in the game and adjust his subjective logical foundations.

"Leaks can also be very risky AND therefore..."

That's a huge difference between him and other people, he is a speculative theorist by nature. Even now he probably won't discard leaking out of hand.

It's not a life lesson about leaking for someone like that, it's a lesson with specific parameters in a specific context.

Is he reinventing the "leaking" wheel in a dumb way? Possibly. But, he's also making the logic his own, which is extremely powerful as experience accrues.

Especially if it turns out that leaking is basically an art one can master, he could probably find a way to master it, because there's no big-picture roadblock in his mind that says "leaking private info to help your case is bad, the end". This is not nuanced enough, i.e. smart enough, for the way his logic operates.

Since he is amenable to working with details, his thinking style has strong long-term flexibility and leverage advantages. Even if it fails hard sometimes.

Just for illustration purposes though. And, once again, I'm not here to talk about his moral character. I also do not believe that he's consciously choosing how to use his personality characteristics. He's working naturally with what he's got, these comfortable, reinforced patterns of good, bad, and everything in between.