The Stuarts were a well-to-do Virginia planter family. The seventh of the ten children, "Jeb," as he was known from the initial letters of his names, grew up at Laurel Hill, the Stuart home place in Patrick County. His father, prominent locally, served a term in the U.S. Congress. Jeb was educated at home, and at Emory and Henry College. He entered West Point in 1850.
Stuart did well at the academy, though he was prone to fighting. Otherwise well-behaved, he was quietly religious and popular with most of his classmates. He graduated a solid 13th in the 1854 class of 46 cadets.
Stuart served in Texas and Kansas before the war. During the Kansas border troubles, he encountered the abolitionist John Brown. In 1859, serving as an unpaid aide to Robert E. Lee while on leave, he identified Brown as the leader of the raid on the Harpers Ferry government arsenal that Lee's command quelled. As early as January 1861, he applied to Confederate president Jefferson Davis for a commission in the Southern army.
As colonel of the 1st Virginia Cavalry, Stuart led a well-timed charge at the first battle of Bull Run (Manassas) that contributed to the Confederate victory on that field. Within a few weeks, he received promotion to command of a cavalry brigade. During the spring of 1862, the brigade performed excellent service screening the army during the withdrawal up the Virginia Peninsula.
On June 11, wit orders to reconnoiter Federal positions, Stuart set out with 1,200 troopers on the first of his famous rides around the Army of the Potomac. Having thoroughly embarrassed the Union forces, he returned four days later with 165 prisoners and 260 captured horses and mules.
The raid won Stuart promotion to major general and command of all the Army of Northern Virginia's cavalry. Rising swiftly to prominence as leader of the "eyes and ears" of Lee's army, he continued his raiding career during the second Bull Run campaign with a visit to the Union Gen. John Pope's headquarters, where he made off with important documents and one of Pope's uniforms. In October, a second ride around Union forces took him to Chambersburg, Pennsylvania. This 126-mile gallop with 1,800 men the final 80 miles without a halt solidified Stuart's reputation for brilliance and dash, and netted the Confederacy another 500 captured horses.
Stuart was a striking, even elegant, figure, solidly built, with a flowing red beard. He wore a handsome gray cape trimmed in red and a cavalier's cocked hat with a gilt star and a lone peacock's plume. He rode a powerful charger. At numerous parties and balls, he cut a fine figure as a dancer. But Stuart led a quietly conventional and sober private life, in spite of his romantic appearance and buccaneering military ways.
His detractors accused him of glory hunting, but Stuart carried out a cavalry commander's routine tasks faithfully. In December 1862, during the Fredericksburg campaign, he launched several strikes against Union communications. His Dumfries Raid at year's end cost the enemy heavily in stolen horses and burned supplies. Stuart kept Lee fully informed of Union movements during the initial phases of the Chancellorsville campaign in late April 1863. When Jackson was wounded on the night of May 2, he handled the II Corps infantry with competence in the final stages of the battle.
As time went on, Stuart found his Federal adversary much improved. His command recovered from an early morning surprise to fight a drawn battle with Union cavalry at Brandy Station in June, the largest mounted engagement of the war. The Confederates inflicted 1,000 casualties on the enemy troopers, double their own losses. After Brandy Station, Stuart effectively screened Lee's flank on the northward march toward Gettysburg, fighting off probing Federal cavalry in skirmishes at Aldie, Middleburg, and Upperville in mid-June.
Only his failure to inform Lee of Union movements during the later stages of the Gettysburg campaign in June 1863 marred an otherwise exemplary war record. He set out on June 24 on another of his long jaunts around the enemy and ruined his military reputation this time. He harassed Union communications in Maryland and Pennsylvania, fought several skirmishes and carried off 125 wagons and 400 prisoners. Lee had little use for wagons and less for prisoners, however. What he wanted was word of his adversary's whereabouts. But Stuart had allowed the Army of the Potomac to get between his cavalry and Lee's main columns. Thus he hovered over the horizon and out of touch for several days, depriving Lee of critical intelligence in the period leading up to the battle of Gettysburg. Lee upbraided him severely the only time in their association the commanding general had ever shown displeasure with Stuart's work.
Stuart's cavalry covered Lee's movements during the opening phases of the Wilderness and Spotsylvania campaigns of May 1864. On May 9, he led out with 4,500 troopers in pursuit of Union Gen. Philip Sheridan's 12,000-strong Cavalry Corps. Stuart reached Yellow Tavern outside Richmond just ahead of Sheridan early on May 11 and took up a position astride the main road to the capital. In an all-day fight, Stuart turned Sheridan away from Richmond, but success cost him his life. Shot in the abdomen late in the afternoon, he died in Richmond the next day.
Stuart's plumed hats, theatrical capes and flowing beard were legendary in the Confederacy. Lee looked past his appearance to assess his military worth in one pithy line: "He never brought me a false piece of information."