Real-World Probability Books: Philosophy of Probability
I have never gained any insight from reading the philosophy of probability,
so am somewhat prejudiced against the whole enterprise.
Hacking, I.
An Introduction to Probability and Inductive Logic.
Cambridge University Press, 2001.
See my amazon.com review.
Kyburg, Henry E. and Thalos, Mariam (Eds.)
Probability Is the Very Guide of Life: The Philosophical Uses of Chance.
Open Court, 2003.
16 articles provide a sampling of modern scholarly activity in the topic.
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