Real-World Probability Books: History of Probability
Many books in the
Popular Science section,
in particular Bernstein and Kaplan-Kaplan,
provide easy to read historical sketches.
David, F.N.
Games, Gods and Gambling: a history of probability and statistical
ideas.
Dover, 1998 (original 1962).
After recounting uses of dice and knucklebones in ancient times,
focuses on development of mathematical probability by mathematicians
from Cardano (1500s) through Galileo, Fermat, Pascal, Graunt,
Huygens, James Bernoulli, Montmort to de Moivre (early 1700s).
A serious scholar writing in serious but readable style, focusing
on specific mathematical contributions and brief biographies rather than the background color
of more popular works.
Devlin, K.
The Unfinished Game: Pascal, Fermat, and the Seventeenth-Century Letter
that Made the World Modern.
Basic Books, 2008.
See my amazon.com review.
Scholarly books
The scholarly works below
are non-technical in the mathematical sense, but too erudite for the general reader;
I merely list the books I own.
Gigerenzer, Gerd et al
The Empire of Chance.
Cambridge University Press, 1989.