This essay examines the first three terms of the Roberts Court and assesses John Roberts' leadership as Chief Justice. It begins by examining Roberts' appointment to the Court, his constitutional views, and his leadership style. It then turns to examine the Court's major decisions and decision-making trends during its first three terms. It concludes by considering the impact of the recent presidential election on the Court and Roberts' leadership going forward. It contends that although John Roberts has impressive skills as a jurist and a leader of the Court, he is likely to find himself (and thus his ability to lead the Court) increasingly at odds with broader developments in the American politics.