On Thursday, October 9, 1862, at Robert E. Lee’s urging, General J.E.B. Stuart left with eighteen hundred Confederate cavalry on a ride which would take him across the Potomac, into the North, and around McClellan’s Army of the Potomac. Stuart had accomplished a similar feat in June during the Seven Days Battle for Richmond.
To antagonize the Northern electorate, Lee sent his boldest cavalry commander to attack the American North once again. It would take Stuart’s command four days to complete its mission. This second raid around the Union army reputedly caused President Abraham Lincoln to remark, "When I was a boy we used to play a game—three times around and out. Stuart has been around him twice. If he goes around him once more, McClellan will be out."