
The Shadow of the Sun by Ryszard Kapuściński. Kapuściński was a Polish journalist who traveled around the (mostly developing) world, reporting on civil wars, coups, revolutions, and other tumultuous events. This book recounts many of his experiences in Africa over several decades and is interesting in its insight into the lives of ordinary people. Someone told me Kapuściński had the most interesting life of anyone in the 20th century and I'm inclined to agree with that.
Congo: An Epic History of a People by David Van Reybrouck. Congo is one of the richest countries in the world in terms of natural resources, but one of the poorest and least functional in terms of economics and institutions. This book gives a good overview of the history of Congo and explains why the problems are so deeply rooted.
The Rise and Decline of Nations and Power and Prosperity: Outgrowing Communist and Capitalist Dictatorships, both by Mancur Olson. Why do some nations develop into relatively free, relatively rich countries, while others stagnate in perpetual conflict and poverty? How can countries transition from one of these states to the other? Why is it so hard to get obviously beneficial changes to occur in developed countries? These books try to answer these questions. I don't think they have the entire answer, and they don't have much in the way of easy solutions, but they get a lot of it right.
Civilization and Its Discontents by Sigmund Freud. I thought Freud was largely discredited and his theories superseded by better ones, but reading this book showed me how insightful Freud really was. He is one of the greatest thinkers of the 20th century. This book helps you answer questions like: Why are most people unhappy? Why do our societies have so many problems? How can we simultaneously satisfy our desire to live in a community with our desire to be independent?
Spring by Knausgaard. I don't think I can do justice to this by summarizing it. It's a beautiful, sad, and short book. Definitely worth reading.
Against Bosses, Against Oligarchies and Contingency, Irony, and Solidarity by Richard Rorty. I'd been hearing a lot about postmodernism, mostly in a derogatory way, over the past year, but I had a hard time believing many of the criticisms of it were true. These two books do a pretty good job of articulating a postmodern worldview and you realize postmodernism isn't the boogeyman it's been made out to be. In fact, it seems like a fairly obvious step from the Enlightenment ideals of rational inquiry to postmodernisms primary project of questioning where the truths that this rational inquiry finds come from and whether they are valuable or not.
The Burden of Responsibility by Tony Judt. Only worth reading if you are interested in French politics. Profiles three French public intellectuals who stood apart from the mainstream in their opposition to totalitarian communism. Not a hagiography; this book offers criticism of these figures at times, though is largely admiring.
As for Winters' book, which I haven't read, it sounds like a more pessimistic version of Olson's Power and Prosperity, which essentially argued that all forms of security arrangement involved those with power extracting money from people, but kings had less incentive to pillage and more incentive to protect than bandits, and democracies more interest in using extracted wealth for public benefit than kings. I doubt Winter would disagree with my characterisation of campaigns for flat taxes as being one of oligarchs' wealth defence strategies in a democracy.