The Power Broker, Robert Caro. Biography of Robert Moses, architect of modern New York City who made every important decision about the city's infrastructure for decades. Moses did enormous damage to the city and its people. Jane Jacobs' The Death and Life of Great American Cities is a counterpoint to Moses' ideas of what a city should be like. Caro's controversial books on Lyndon Johnson are also captivating.
Battle Cry of Freedom, James McPherson. Much more than another recounting of battles and generals. McPherson places the war in its economic, social, and political context in American history.
Slavery by Another Name, The Re-Enslavement of Black Americans from the Civil War to World War II, Douglas Blackmon. I can't overstate how fundamentally this book changed my understanding of American history. Throughout the South, blacks were systematically arrested for little or no reason and either sentenced or sold to plantation, mines, factories, and other white businesses and forced to work for years until dead or useless. In many ways this was worse than slavery, since slavers at least had some incentive to maintain their property. Convict slavery continued until changing economics made the system less profitable and Franklin Roosevelt's administration determined it undermined American propaganda against the Nazis and Japanese.
Guns, Germs, and Steel and Collapse, Jared Diamond The first book presents a non-racial explanation for differing patterns of development throughout the world, identifying the distribution of resources as the key factor. The second book traces the failure of different societies with frightening parallels to the 20th century.
W.E.B. DuBois: Biography of A Race 1868-1919 and The Fight for Equality and the American Century, David Levering Lewis
