You find insight into playing the races from all walks of life.  One common area of overlap is with the financial world.  Written in 1998 (but still very relevant) Jacob Weisberg profiles then-Treasury secretary Robert Rubin with a focus on his probabilistic way of thinking. Two quotes from this must-read:

“At Harvard and Yale Law School I learned to think about the uncertainties and the ambiguities of life intellectually,” he says. ”When I got to Goldman, Sachs, I learned it was a matter of financial life and death to learn to be probabilistic. If you thought in absolutes and black-and-whites, sooner or later you got wiped out. The odds would catch up with you.”

“What was paradoxical about Rubin’s risk-taking was how reasoned it was. ”Arbitrage is an actuarial business, just like so much of life,” Rubin says. ”Each judgment was probabilistic. What you needed to do was make sure you didn’t get so big in one position, even if the odds were very good, that if it went bad it wiped out everything else. You had to maintain your balance.’

Full NY Times article here

Those looking deeper may also enjoy Rubin’s biography available at Amazon: