Just wanted to flag that the works of Ian Hacking, especially The Emergence of Probability (1975) and The Taming of Chance (1990) are excellent on this. Dense and challenging at times but also well written and the product of a very original mind.

The latter book has a Wikipedia page with some more info - was surprised to see Hacking not mentioned here since the featured article is partly based on his work: https://en.wikipedia.org/wiki/The_Taming_of_Chance