There is an episode[1] of NPR's Throughline that covers some of this. That episode was excerpted into a Planet Money episode[2] as well.

[1]: https://www.npr.org/2022/06/29/1108728257/do-not-pass-go

[2]: https://www.npr.org/2023/01/25/1151367036/story-monopoly-ame...