This book presents a provocative account of James Madison's political thought by focusing on Madison's lifelong encounter with the enduring problem of constitutional imperfection. In particular, it emphasizes Madison's alliance with Thomas Jefferson, liberating it from those long-standing accounts of Madisonian constitutionalism that emphasize deliberation by elites and constitutional veneration. Contrary to much of the scholarship, this book shows that Madison was aware of the limits of the inventions of political science and held a far more subtle understanding of the possibility of constitutional government than has been recognized. By repositioning Madison as closer to Jefferson and the Revolution of 1800, this book offers a reinterpretation of one of the central figures of the early republic.