Stuart graduated from West Point in 1854, and served in Texas and Kansas with the U.S. Army. Stuart was a veteran of the frontier conflicts with Native Americans and the violence of Bleeding Kansas, and he participated in the capture of John Brown at Harpers Ferry. He resigned his commission when his home state of Virginia seceded, to serve in the Confederate Army, first under Stonewall Jackson in the Shenandoah Valley, but then in increasingly important cavalry commands of the Army of Northern Virginia, playing a role in all of that army's campaigns until his death.
He established a reputation as an audacious cavalry commander and on two occasions (during the Peninsula Campaign and the Maryland Campaign) circumnavigated the Union Army of the Potomac, bringing fame to himself and embarrassment to the North. At the Battle of Chancellorsville, he distinguished himself as a temporary commander of the wounded Stonewall Jackson's infantry corps.
Stuart's most famous campaign, the Gettysburg Campaign, was flawed when his long separation from Lee's army left Lee unaware of Union troop movements so that Lee was surprised and almost trapped at the Battle of Gettysburg. Stuart received criticism from the Southern press as well as the proponents of the Lost Cause movement after the war. During the 1864 Overland Campaign, Union Maj. Gen. Philip Sheridan's cavalry launched an offensive to defeat Stuart, who was mortally wounded at the Battle of Yellow Tavern.

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