This paper seeks to accomplish three things. First, it contextualizes Ralph Waldo Emerson's political thought by demonstrating that, despite his rhetoric to the contrary and the dominant interpretation within Emersonian scholarship, his political ideas had an intellectual genealogy rooted both in his local New England context and in the broader American culture. Second, it argues that principles and tensions from the Federalist Party lingered long after the demise of the organized group, especially in response to the perceived excesses and extremes of Jacksonian America, and can even be found within a thinker as egalitarian and democratic as Emerson. And finally, the article explores how the ironies of these two previous points flesh out the paradoxical and dynamic nature of America's democratic tradition. By engaging the ironies and paradoxes within Emerson's political thought in microcosm, I argue, one gets a better view of the larger issues at stake within the broader culture.