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Concern about political ambition in the American polity, particularly surrounding the presidency, stems back to debates surrounding ratification of the Constitution. While presidency scholarship generally anticipates that presidents will be ambitious in office, prior efforts at evaluating presidential ambition tend toward psychoanalytic approaches. This work focuses more on presidents’ latent psychological characteristics than on the actual manifestations of their ambition (what they attempt to accomplish as the nation’s chief executive). Reversing field, I offer a three-dimensional conceptualization of presidential ambition that instead evaluates the ambition of a president’s governing agenda. I define this measure with reference to 1) the salience of -- and polarization surrounding -- the issues presidents elevate, 2) the depth of the change they pursue on these issues, and 3) the pace and structure by which they promote their initiatives. Using this framework, I evaluate the governing agendas advanced by every newly elected, first-term president from John F. Kennedy onward and argue, contrary to existing accounts of presidential agenda construction, that modern presidents advance ambitious agendas regardless of the political environments they confront. In fact, I show that the relationship is more the inverse: presidents who seemingly come into office “less empowered” often pursue more ambitious agendas. I conclude by discussing the implications of this dynamic for democratic elections and suggest institutional remedies.