I am reading a 2003 book by editor and journalist Fareed Zakaria about democratic transitions. His thesis is relatively simple: usually it’s better to have a strong free market and constitutional liberties before a country transitions to democracy. There are lots of caveats (resource-rich countries that don’t need to tax their people), but it holds up pretty well. Poor, less-educated populations can be less liberal than autocratic rulers who wish to modernize. It’s a simple book, but Zakaria is even-handed with the historical cases and references some statistical analysis as well.
He quotes a 13 century Turkish poet, Yusuf:
To keep the realm needs many soldiers, horse and foot;
To keep these soldiers needs much money;
To get this money, the people must be rich;
For the people to be rich, the laws must be just.
Here’s the book: The Future of Freedom: Illiberal Democracy at Home and Abroad