The Secession Winter of November 1860-January 1861 represented the most trying time of President James Buchanan’s tumultuous administration. Throughout the crisis, Buchanan leaned heavily on Secretary of War John B. Floyd and Attorney General turned Secretary of State Jeremiah S. Black, both of whom had differing views on the issue of secession. While Black remained fervent in his belief that prompt action was required to combat secession, Floyd remained adamant that peace needed to be maintained between the North and South, even if it meant sacrificing the federal Union. To explain the reasons for Buchanan’s flawed decision-making during secession, this paper highlights the personal nature of the relationships Buchanan shared with Black and Floyd throughout the crisis, which led Buchanan to pursue policies that weakened the federal presence in Charleston, South Carolina, and ensured that, by January 1861, any efforts to avert a conflict had been rendered impossible to implement.