Ulysses S. Grant’s views toward slavery before the Civil War have been a point of strong debate among historians. Few letters exist from Grant’s time as a farmer in St. Louis, Missouri (1854–59), leading most scholars to excessively rely on postwar reminisces and Grant’s own memoirs to argue that he consistently opposed slavery. This essay explores Grant’s relationship with slavery when he lived in St. Louis. It also questions conventional wisdom by arguing that Grant did not hold a lifelong aversion to slavery. Rather, his views evolved during his tenure as a U.S. general during the American Civil War. As the contingencies of a prolonged and bloody conflict pushed the Lincoln administration to support emancipation as a war measure to defeat the Confederacy, Grant realized that the end of slavery was necessary for Union victory and as an effective postwar reconstruction.