Born in Virginia and a graduate of West Point (class of 1854), Stuart was already a first lieutenant in the United States Army 1st Cavalry and a veteran of Indian fighting on the plains and of Bleeding Kansas when, he carried orders for Robert E. Lee to proceed to Harpers Ferry to crush John Brown's raid. Stuart volunteered to be Lee's aide-de-camp, and read the ultimatum to Brown before the final assault. Promoted to captain on April 22, 1861, Stuart resigned on May 14, 1861 to join the Confederate States Army.
His later appointments included:
The following May at the Battle of Chancellorsville, Stuart was appointed by Lee to take command of the 2nd Army Corps for a few days after Stonewall Jackson had been wounded. Returning to the cavalry, he commanded the Southern horsemen at Brandy Station, the largest cavalry engagement on the American continent, on June 9, 1863. Although the battle was a draw, the Confederates did hold the field. However, the fight represented the rise of the Union cavalry and foreshadowed the decline of the formerly invincible Southern mounted arm. During the Gettysburg Campaign, Stuart, acting under ambiguous orders, again circled the Union army, but in the process deprived Lee of his eyes and ears while in enemy territory. Arriving late on the second day of the battle, Stuart failed the next day to get into the enemy's rear flank, being defeated by Generals Gregg and Custer.
During Grant's drive on Richmond in the spring of 1864, Stuart halted Sheridan's cavalry at Yellow Tavern on the outskirts of Richmond on May 11. A Union sharpshooter (at a distance of thirty feet) shot him; he died the next day in the rebel capital. He is buried in Hollywood Cemetery there.
Like his intimate friend, Stonewall Jackson, General Stuart was a legendary figure, ranking as one of the greatest cavalry commanders of all time. Stuart was a son-in-law of Brigadier General Philip St George Cooke of the Federal service; his wife's brother was Brigadier General John Rogers Cooke of the Confederacy.