This book shows how Henry Adams (grandson of President John Quincy Adams and great-grandson of President John Adams) looked at the South during various phases of his life. It explores the cultural and familial impulses behind those views and locates them in US intellectual history.

O'Brien then covers a number of topics relevant to Adams's outlook on the South, including his residency in that deceptively "southern" city, Washington, D.C. his journalism on the Reconstruction-era South; his biographical or historical works on the Virginians John Randolph, Thomas Jefferson, and James Madison; and his two novels, especially Democracy. Finally, O'Brien ponders the vein of southern self-criticism - exemplified by Wilbur J. Cash's Mind of the South - that embraces the notorious slur so often quoted from The Education of Henry Adams.