This study argues that the movement of enslaved people toward Union Army positions during the U.S. Civil War hastened the political process of emancipation by creating facts on the ground for the Lincoln White House and the Republican Congress to act upon. The study further argues that the shambling and improvised task of 19th century emancipation was a compressed reflection of the disordered process of the adoption of legalized slavery in the Virginia Colony during the 17th century. As it happens, both initiated at the same piece of land: Old Point Comfort at the eastern end of the Virginia Peninsula. The study examines the sociology of the “contraband camps” that first formed near Fort Monroe, Virginia and later spread to hundreds of other places across the South, followed by an analysis of their effect on the speed of political emancipation. The subject of Lincoln’s evolving thinking on the subject and a discussion of his decision-making process is also key to understanding how the movement of up to 800,000 enslaved people to the contraband camps became a major driver of the turn toward emancipation as a higher moral cause for the Union side in the Civil War, as well as the formation of the U.S. Colored Troops and the eventual Constitutional amendment abolishing slavery.