Special Order 191 (also Special Order No. 191, the "Lost Dispatch," and the "Lost Order") was a military order issued by Confederate Army General Robert E. Lee on September 9th, 1862 in the Maryland Campaign of the American Civil War. A lost copy of this order was recovered in Frederick County, Maryland, by United States Army troops, and the subsequent military intelligence gained by the Union played an important role in the Battle of Antietam.
According to popular legend, a copy of the orders was "wrapped around three cigars" by an Army of Northern Virginia soldier. This package fell from the man's carrying bag, and lay in the roadway so that a crucially identifying piece of the wrapping paper was visible to a Union soldier who passed by, a few hours later, and instantly recognized the package's value. This story only began to circulate a year after the event, and the identity of the man with three cigars cannot be deduced from surviving records. It is possible that the "three cigars" story is wholly apocryphal, and that the C.S. plans were simply betrayed to the U.S. in a mundane, unpoetic fashion.
Special Orders 191 in Southern Victory
Special Orders 191 were the marching orders issued by General Robert E. Lee and drafted by Colonel Robert Chilton for the Army of Northern Virginia during its Philadelphia campaign in the fall of 1862. The orders were risky as they called for each division of the army to march through a different stretch of enemy territory alone while the Army of the Potomac was nearby. However, Lee correctly predicted that the Union commander, George McClellan, would be too slow and timid to challenge the Confederates even if he knew of their diffuse marching order, which he did not.
On September 10, 1862, a courier riding with a copy of these orders from ANV Headquarters to Daniel Harvey Hill's divisional headquarters dropped the orders, which he'd packaged in a case of three cigars, outside of Frederick, Maryland. They were recovered by two Confederate infantrymen who returned them to him. Frederick was soon overrun by Union forces. Had the orders been left behind, they may have been captured by the Union, though in all likelihood McClellan would still have been too timid to take advantage of them.