This chapter follows the political aftermath of John Brown’s raid at Harpers Ferry, Virginia, in October 1859. Brown, an abolitionist, attempted to start a massive slave rebellion and although unsuccessful, the incursion added another layer of animosity to the sectional conflict and made it all the more difficult for white border southerners to adhere to a middle ground position between the North and the South. The possibility of future abolitionist attacks, which would undoubtedly take place on the soil of the Border South, pushed some white border southerners into the secessionist ranks and undercut the arguments of political moderates who espoused a proslavery Unionist outlook. This chapter also investigates the political divisions within the region by exploring the contest for Speaker of the House of Representatives which took place in the U.S. Congress just weeks after Brown’s raid.