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In his first four years as Chief Justice of the United States, William Howard Taft convinced Congress to pass two reform bills that substantially enhanced the power of the federal courts, the Supreme Court, and the Chief Justice. In this article, I explore the causes and the consequences of those reforms. I detail how Taft's political entrepreneurship—specifically the building of reputations, the cultivation of networks, and the pursuit of change through measured action—was instrumental in forging judicial autonomy and, subsequently, how that autonomy was employed to introduce judicial bureaucracy. By asking both how judicial reform was accomplished and what judicial reform accomplished, I offer an analytically grounded and historically rich account of the politics surrounding two of the most substantively important legislative actions relating to the federal judiciary in American history. In the process, I also draw attention to a largely neglected story of political development: the politics surrounding the building of the federal judiciary as an independent and autonomous institution of governance in American politics.