ECW welcomes back guest author Lloyd W. Klein
General Robert E. Lee issued Special Order #191 on September 9, 1862. The order directed his corps commanders’ movements for the start of the Maryland Campaign. Soldiers of the Union army found a copy of the order on September 13, and it has subsequently become known as “The Lost Order”. The Lost Order revealed that each part of the Confederate Army was separated by several miles from the others and that the two largest units were 20 to 25 miles apart on either side of the Potomac River. This military intelligence likely encouraged Major General George McClellan in his planning and to advance his army with confidence, and is traditionally considered to have been an important influence in the Battles of South Mountain and Antietam.
What was Special Order #191?
In Special Order #191, General Lee outlined in detail the routes his army would take during the invasion and the timing for the attack of Harpers Ferry. The crucial aspect of Lee’s plan was to divide his army during the early part of the invasion, and then regroup later. Lieutenant General Thomas “Stonewall” Jackson was to lead the advance and capture Harper’s Ferry while Major General Daniel Harvey Hill was ordered to guard its rear.
Lieutenant Colonel Robert H. Chilton, Lee’s assistant adjutant general (chief of staff), wrote out 8 copies of the order while at Lee’s camp on the Best farm, 3 miles south of Frederick, MD. These copies were transcribed and sent to each of the generals involved and to President Jefferson Davis by courier.
Union troops discovered a copy of the order 4 days later in a farm field about half a mile north of where Lee’s camp was located. The order was in an envelope wrapped around three cigars lying in the grass at a campground that General Hill and his command had recently vacated.
Whose Copy of the Order Was Lost?
Chilton unquestionably wrote the copy of the order found in the field. Hill did receive a copy: but it is in Jackson’s handwriting, not Chilton’s. Hill was adamant for the rest of his life that he only ever received this one copy. The mystery of the loss of the Order centers on the fact that Hill received the copy written by Jackson, which he kept forever, but not the copy from Chilton. That copy is the “Lost Order.”
The presence of duplicate orders to the same general is the foundation of this mystery, and provides some insight into what happened. At the time that Special Order #191 was written, Hill was under the command of Jackson, his brother-in-law. Jackson personally copied the document for Hill, because once the army crossed into Maryland, the order specified that Hill was to exercise independent command as the rear guard. For this reason, Jackson copied and sent Hill the order because he didn’t know if Chilton had done so. But, since Special Order #191 conveyed Hill’s having an independent command once entering Maryland, Chilton had in fact sent Hill a copy.
Chilton did not learn of the order having gone missing until a year later when it was revealed as part of a US Government investigation. He was surprised to learn of it because the envelope should have been returned signed by the receiving staff officer, otherwise an inquiry would have followed. He did not know why this missing envelope was never recognized. Years later, Chilton could not remember which officer he had dispatched as a courier to Hill.
Plausible Candidates for the Culprit
To this day, no one knows who lost the order. There are only three plausible candidates: Chilton’s courier, a member of Hill’s staff, or Hill himself. This order dictates the overall strategy of the Army of Northern Virginia in a major offensive operation. How did such an important document end up in a farmer’s field still in the original envelope?
One obvious clue is that whoever last had possession was a cigar smoker. But it can be deduced that the presence of the cigars, which was not disclosed for 2 decades after the war, is even more meaningful. The detail of personal cigars in the envelope demonstrates that this copy of the order had either been delivered or was never going to be delivered, since the envelope was serving as a humidor. Also, it suggests that it was undoubtedly “lost”; if it had been purposely discarded, the cigars would have been removed.
We can reason that whoever last possessed the order must have known that it was not, at the moment of the loss, of proximate importance to General Hill. This is a logical deduction because otherwise its loss would have caused immediate difficulty and prompted an immediate search. Further, since Jackson had to have received the order (he was in the same field at the time as Lee), written his version, and had it delivered to Hill, its loss can be presumed to have occurred later than the initial deliveries of Chilton’s copies. It was found in Hill’s abandoned camp, which is less than a mile from where Lee was, implying that it did get to the right place.
The most frequently postulated possibility is that Hill did receive both orders, and lost one of them. After the war, this was the standard view, but Hill always denied it. He expected that his orders would come from Jackson, his superior officer, so the fact that none came from Lee did not surprise him. He claimed that he had pinned the version he had received in his pocket, knowing its importance. His chief of staff always maintained that only one version was received. After the war, Hill even sent a letter to Lee detailing the events and asking for clarification. He carried the copy he had received to show to everyone that he, indeed, had kept his copy of the order. Hill was a highly intelligent but cantankerous individual who was an excellent battlefield general; it is hard to imagine someone of his caliber losing such an important document. He was a very religious man who has not been reported to smoke.
Hills’ chief of staff also denied receiving two copies, saying that had an order from General Lee arrived at headquarters, it would have been handled carefully and with documentation: it would have been stamped and the return envelope signed and returned to the courier. Certainly, no cigars would have been placed in the envelope. Major James W Richford was Hill’s adjutant general, who gave sworn testimony that it was his duty to receive such orders and the only one he ever saw was that from Jackson. The fact that the envelope was not signed by him is strong supporting evidence that it was never formally received.
Another possibility to consider is that the culprit was the courier, who accidentally dropped the envelope while on his way to deliver it to Hill. But the distance from Lee’s headquarters to Hill is less than a mile, a few minutes ride by horse, and no courier would have found that an opportune time to open a dispatch from General Lee and place his cigars in the envelope. Moreover, the orders were found near Hill’s camp, not along a road or in the bushes.
Having discarded the simple explanations, a more complicated story must be hypothesized. One key question is: why was Chilton lax about checking whether the envelope was returned signed, as was the standard practice?. He was a highly conscientious officer and his subsequent activities during and after the war demonstrate a decidedly competent, detail-oriented man. His denial of remembering who was the courier was made in a letter to Jefferson Davis in 1874. It is at least as credible that Chilton knew exactly who he had sent with the orders and was covering up the identity years later. Doing that would be surprising if the man didn’t survive the war or had descended to obscurity, but would be exactly the honorable thing to do if the man was prominent and still alive, and whose reputation would be harmed.
So, Who Lost The Order?
If that were the case, a very serious candidate would be Henry Kyd Douglas. He has been considered a potential culprit, though there is no direct evidence.
Kyd Douglas was a young lieutenant on Jackson’s staff at the time of Antietam, often serving as courier. It is not a stretch to conjecture he was at Lee’s HQ having just delivered dispatches, and that Chilton asked him to drop off the order at Hill’s encampment, just up the road. Douglas might have recognized on his arrival that Hill had already received orders from Jackson and never formally delivered them, or tried to but was told it had already been received. Perhaps before returning he stopped for refreshment in the camp and the envelope fell from his pocket. He could have returned to Jackson without the envelope without any alarm, since the orders called for advancing early the next morning.
He was a great asset to the Confederate leadership at Antietam because he grew up about four miles from the battlefield. He left Jackson’s staff in October – 1 month later – a fact that some have speculated was retribution for losing the order. He was appointed Captain of Co. C of the 2nd Virginia Infantry and later appointed Inspector General of the “Stonewall” Brigade. Afterwards, he joined the staff of General Edward Johnson, and was promoted to Major. He was wounded and captured at Gettysburg, and held as a prisoner at Johnson’s Island, Ohio, until exchanged in March 1864. He was later staff officer to Generals Gordon and Early, and saw action in the Overland, Shenandoah Valley and Petersburg campaigns. He commanded a Virginia brigade at Appomattox. He was involved as a witness in the investigation of the assassination of President Lincoln, but he was not implicated.
Wounded six times, Henry Kyd Douglas returned to the practice of law in Maryland after the war. He was a very popular speaker and a respected trial lawyer. He also was prominent in veterans affairs; he helped to establish a permanent cemetery in Hagerstown, Maryland, for Confederate soldiers killed at Antietam. He was involved in local politics, running unsuccessfully for Congress and serving briefly as a justice on the Maryland Court of Appeals. Why would Chilton damage his reputation unnecessarily after the war by identifying him?
Douglas’s memoirs, I Rode with Stonewall: The War Experiences of the Youngest Member of Jackson’s Staff, are not considered reliable; they are said to be filled with exaggerations. They do not relate where he was at the critical time on September 9th.
Incidentally, he smoked cigars.
Dr. Lloyd W. Klein is Clinical Professor of Medicine, University of California, San Francisco. He is a nationally recognized cardiologist with over thirty-five years’ experience and expertise. He is also an amateur historian who has read extensively and published previously on the Civil War, with a particular interest in political and military leadership and their economic ramifications.
- Stephen W. Sears, Landscape Turned Red: The Battle of Antietam. Boston: Houghton Mifflin.
- James McPherson, Battle Cry of Freedom. The Civil War Era. Oxford University Press, 1988.
- General Robert E. Lee’s “Lost Order” No. 191 https://www.battlefields.org/learn/primary-sources/general-robert-e-lees-lost-order-no-191
- Joe Ryan. “Special Order 191: Ruse of War”. Joe Ryan Civl War.com. https://www.joeryancivilwar.com/Special-Order-191/Ruse-of-War.html
- Wilbur D Jones. “Who Lost the Lost Order? Stonewall Jackson, His Courier, and Special Orders No. 191.” Civil War Regiments: A Journal of the American Civil War, Volume 5, No. 3, 1997; and http://www.geocities.ws/Pentagon/Barracks/3627/loser.html