James Oakes was sitting at the head of a frighteningly tiny conference table when I entered the room for my first graduate course at the CUNY Graduate Center many years ago. A professor of American history, his intensely thoughtful approach to the discipline impressed and, of course, intimidated me. I've since come to know him as a serious and generous scholar, whose work on slavery and abolitionism serves, to me, as a great model for how politics and history can be effectively interwoven. In this conversation, we talk about his focus on slavery and the Civil War, his response to Lincoln's radical critics, and why he prefers to explore his politics, at least publicly, through the study of the 19th century.