Confederate General J.E.B. Stuart begins his ride around the Army of the Potomac during the Peninsular campaign in Virginia, after being sent on a reconnaissance of Union positions by Robert E. Lee. Four days later, Stuart had circled the entire Yankee force, 105,000 strong, and provided Lee with crucial information.
General George McClellan spent the spring of 1862 preparing the Union army for a campaign against Richmond up the James Peninsula. By late May, McClellan had inched up the James with relatively light fighting. But after Joseph Johnston was wounded at the Battle of Seven Pines on May 31, Robert E. Lee assumed command of the Army of Northern Virginia. In the next month, Lee began to show the gambling spirit that eventually earned him a reputation as one of history's greatest generals.
Lee dispatched Stuart, his dashing cavalry leader, and 1,200 troopers to investigate the position of McClellan's right flank. Stuart soon discovered that McClellan's right flank did not have any natural topographic features to protect it, so he continued to ride around the rest of the army in a bold display that exceeded Lee's orders. His troopers took prisoners and harassed Federal supply lines. They rode 100 miles, pursued by Union cavalry that was commanded, coincidentally, by Stuart's father-in-law, Philip St. George Cooke. The Confederate cavalry was far superior to their Yankee counterparts, and the expedition became legendary when Stuart arrived back to Richmond on June 15. The information provided to Lee helped the Confederates begin an attack that eventually drove McClellan from Richmond's doorstep.