In the annals of the Civil War, nobody mixed competence with charm quite like JEB Stuart (1833-1864), the legendary Confederate cavalry leader of Robert E. Lee’s Army of Northern Virginia. The quintessential Southern gentleman, Stuart was equal parts great and grandiose, playing the traditional reconnaissance roles masterfully while dressing the part, with capes, sashes, and an ostrich plumed hat, while sporting cologne and a heavy beard (which according to some was grown to hide his weak chin). Stuart reveled in his fame after riding around the entire Union Army of the Potomac twice in 1862, embarrassing the North in the process, but he also proved to have an eye for tactics and strategy, particularly at Fredericksburg and Chancellorsville. However, Stuart’s skills and pomp have long been counterbalanced by his controversial ride before the Battle of Gettysburg. Given great discretion by Lee, who trusted him so much, Stuart led his cavalry in a roundabout operation that sought to embarrass the Union army but instead ended up being too far removed from the Army of Northern Virginia to warn Lee of the Army of the Potomac’s movements. Lee’s army inadvertently marched into the Union army at Gettysburg, touching off the largest battle in the history of North America, and Stuart has long been cited as one of the scapegoats for the loss. With his record, personality traits, and controversy, Stuart has long been one of the most identifiable figures of the Civil War. This short essay by Charles H.L. Johnston covers his entire life.