I have nothing that looks like an answer, but I wanted to put the question out to start a discussion. I especially hope that this leads to someone here researching the question well. I also have almost nothing to back up the claims below.
I became curious about this from thinking about how to find people who can make progress in MIRI's Agent Foundations questions. It seems to require very high levels of both math and philosophy, and I want to know how to select for both of these skills simultaneously.
It seems like many of the great mathematicians at least had enough of an interest in philosophy to share their philosophical opinions. Also it appears that the people who substantial progress in philosophy often use math. (There are of course disagreements about what makes good philosophy, and I am biased in favor of the mathematical flavored philosophy.)
I am especially surprised by the fact that the tails seem to come together rather than apart. It seems like mediocre mathematicians and philosophers are much less likely to be interested in the other field.
Some possible theories:
1) I am noticing a pattern that is not there.
2) This is a consequence of the fact that all intelligence is correlated, and you will notice a similar pattern between many pairs of fields.
3) Mathematics and Philosophy are very old fields. Historically, fields did not really exist, and people were more interdisciplinary. If you look at modern mathematicians and philosophers, the trend goes away.
4) The skill to produce great math and skill to produce great philosophy are secretly the same thing. Many people in either field do not have this skill and are not interested in the other field, but the people who shape the fields do.
Thoughts?
Training in different disciplines will teach you different skills. Maths is great for leaning to think precisely as if you mess up, someone will be able to show you a formal proof of why you are wrong. In contrast, it is much harder to learn to think precisely purely by studying philosophy as the claims and arguments are less well defined. It's very hard to get the logic flow clear enough that someone could formally prove that your argument is either logically sound or logically unsound. Without the same feedback loop, your ability to think precisely simply won't advance as fast.
However, someone who has trained extensively in maths might face the opposite problem of being stuck in that paradigm. Perhaps they want ever claim to be put into a formal model before they are willing to consider it, without understanding that this is too much of a burden for some areas of philosophy and that they would be missing out on valuable lessons.
So I expect this would lead to a bipolar distribution where some mathematical philosophers crash and burn, whilst others soar.