Between 1768 and 1834 Harvard College’s “Rebellion Tree” stood as a totem of liberty for students, whose acts of rebellion against Harvard mirrored the nation’s cultural and ideological schisms in foreshadowing the Civil War. Contrary to historiographical arguments that these boys stood aloof to slavery, this dissertation argues that the institution was singularly important in shaping their worldviews. Indeed, the generation that saw combat in the Civil War played a minimal role in its onset. By positioning Harvard students within the broader contexts of societal and political developments, this dissertation sheds light on higher education’s role in laying the intellectual and cultural foundations of the Civil War. It explores the connections between student ideologies, familial legacies, and intellectual and emotional paradigms in explaining the origins of the nation’s bloody rupture. In doing so, it delves into the politics of race, class, and gender in shaping the worldviews of the nation’s patriarchal elites, from both Northern and Southern sections. Furthermore, it critically assesses the efficacy of Harvard’s republican education amidst escalating campus divisions, revealing how republicanism’s principles waned against the rising tide of civil religion as the College transitioned from a place of unity to a microcosm of national discord. This research contributes to the “long history” school of Civil War causation and the historiography of higher education by assessing Harvard’s role in shaping youth worldviews. It also adds to scholarship about the history of emotions in exploring the interconnectedness of politics, knowledge, and feeling in American democracy. The ultimate purpose of this study is to elucidate societal expectations of masculinity and higher education amid ideological polarization. Particularly, the ways colleges and universities can be instrumental in mitigating—or exacerbating—civil conflict. This study serves as a cautionary tale about enduring battles within American society for cultural dominance and how these battles prefigure the culture wars that extend into posterity.