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The “Lost Order” Of General Lee


Portrait of Gen. Robert E. Lee, officer of the Confederate Army, The Library of Congress Prints & Photographs Online Catalog;

The “Lost Order” Of General Lee General Robert E. Lee issued Special Order #191, which has become known as “The Lost Order”, on September 9, 1862, during the Maryland Campaign. 

The order directed his corps commanders’ movements for the campaign. Soldiers of the Union army found a copy of this order on September 13.

The military intelligence gained allowed General McClellan to advance his army with confidence, and thus was a decisive element in the Battles of South Mountain and Antietam.

Battle of South Mountain

What was Special Order #191?

In Special Order #191, General Lee outlined the routes his army would take and the timing for the attack of Harpers Ferry. It provided specific details of the movements for his army during the invasion of Maryland. The crucial aspect of Lee’s plan was to divide his army during the early part of the invasion, and then regroup later.  The order directed Major General Stonewall Jackson to move his corps to Martinsburg while McLaws’s and Walker’s divisions “endeavored to capture Harpers Ferry.” Major General James Longstreet was to move his corps northward to Boonsboro. Major General DH Hill’s division was to act as rearguard on the march from Frederick.

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General Lee wrote the order while camped out in this field on Best’s Farm, 3 miles south of the town of Frederick, Maryland.  Photo by the author.

Robert H. Chilton wrote out the 8 copies of the order and signed them in Lee’s name. He was assistant adjutant general with the rank of lieutenant colonel serving on the staff of General E. Lee, rising later to chief of staff and was promoted to brigadier general.

A copy of the order was sent to each of the generals involved by courier.  A total of 8 copies of the order were transcribed and sent to: Generals Jackson, Longstreet, Walker, Stuart, McLaws, Taylor, DH Hill & President Jefferson Davis.

A copy of the order was found by complete happenstance in a farm field about half a mile north of Best’s Farm. The order was in an envelope wrapped around three cigars lying in the grass at a campground that General Hill had recently vacated. The union soldier who found the order recognized immediately the importance of the document. 

Whose copy of the Order was Lost?

Confederate troops on the march

You might wonder if a copy of the “Lost Order” was lost, who didn’t receive their copy? And how did they know where to go without it? This is where the mystery gets complicated and interesting.

The copy of Special Order191 recovered by Union troops is addressed to General DH Hill. But the strange thing is, Hill received a copy of the order. We know this because it still exists; and actually, both copies do. And both are authentic. 

R.H. Chilton undoubtedly wrote the letter found in the field. The copy Hill actually received is in Stonewall Jackson’s handwriting, not Chilton’s. DH Hill was adamant for the rest of his life that he only ever received this one copy. 

At the time that Special Order 191 was written, DH 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 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. 

The actual Lost Order found in the field by Union Soldiers. It resides today at the Smithsonian Institute in Washington DC

The mystery of the loss of the order centers on the fact that Chilton did send Hill a copy, and that Hill was also sent the order from Jackson. Hill received Jackson’s copy, which he kept forever, but the copy from Chilton he said he never received. That copy is the “Lost Order.”  

Chilton did not learn of the order having gone missing until much later, and was surprised because he was certain that the signed envelope would have been returned or an investigation would have followed. He did not know why that was never recognized. Years later, Chilton could not remember which officer he had dispatched as a courier to Hill.

Siege of Vicksburg

So, why was the letter not delivered to Hill? This order dictates the overall strategy of the Army of Northern Virginia, and therefore is a critical movement order. It should have been delivered directly to DH Hill himself. How did such an important document end up in a field wrapped around three cigars?

As shown in the map, Lee wrote the order in a field on the Best Farm right behind the house and barn. The field it was found in is located less than a half mile up the road, today located in front of the NPS headquarters. The Best Farm is located 3 miles outside of Frederick, Maryland, and coincidentally was a key Confederate artillery position in the 1864 Battle of Monocacy. A historical marker on the Monocacy National Battlefield commemorates the finding of Special Order 191 during the Maryland Campaign.

From the National Park Service https://www.nps.gov/mono/learn/historyculture/an-invitation-to-battle.htm 

Sears in Landscape Turned Red suggests the possibility that Hill did receive both orders. but then misplaced them.  During and after the war, this was the standard thought, but Hill always denied it. He even sent a letter to Lee after the war detailing the events and asking for clarification. He always carried the copy he had received in his pocket to show to everyone that he, indeed, had kept his copy of the order.

Only Chilton’s courier, Hill’s staff, or Hill himself could have been the culprit who lost the order. And the battle turned on its loss. 

Robert H. Chilton, Confederate general

The Order Found

Around 12 noon on September 13, a Union soldier on a skirmish line found an envelope. On opening it, Corporal Barton W. Mitchell of the 27th Indiana Volunteers, part of the Union XII Corps, found 3 cigars wrapped inside a note. Mitchell did not read every word, but he noticed that it concluded with the phrase “By command of General Robert E. Lee” and was signed “R.H. Chilton, Assistant Adjutant General”.

Mitchell recognized the significance of the document and showed it immediately to Sergeant John M. Bloss. The note was elevated up the 27th Indiana’s chain of command: to Captain Peter Kop, Colonel Silas Colgrove, then to Brigadier General Alpheus Starkey Williams, commander of the XII Corps. 

An aide to General Williams recognized the signature of R. H. Chilton as authentic.  Williams’s aide, Colonel Samuel Pittman, recognized Chilton’s signature as authentic.   By complete coincidence, Pittman had worked for a Detroit bank before the war during a time when Chilton was paymaster at a nearby army post. Pittman recognized Chilton’s signature because he often paid drafts signed by him. 

Implications of the Lost Order

General McClellan

Consequently, when General McClellan came into its possession, he had an accurate and timely picture of exactly where the components of the Confederate army were located and what routes they were going to be using in the next several days. He knew that the confederate army was divided and he knew exactly where they were.

McClellan received the order that afternoon. Upon receiving Lee’s “Lost Order”, McClellan said: “Here is a paper with which, if I cannot whip Bobby Lee, I will be willing to go home.”  Nevertheless, he delayed troop movements for a critical 18-hour period. Furthermore, had he moved more rapidly, he might well have caught Lee and trapped him. His intention was to cut the Confederate Army in two.

The Battle of Shiloh

At 3PM, McClellan sent the order to his cavalry chief, General Alfred Pleasanton and told him to find out if the Confederate movements in the order had been followed. In a 6:20 p.m. message to VI Corps commander General William Franklin, McClellan informed him about the order and what he was able to discern about how closely they had been followed. Still, he did not move his troops until the next morning, losing valuable time. 

McClellan told Lincoln, “I have the whole rebel force in front of me, but am confident, and no time shall be lost…I think Lee has made a gross mistake and that he will be severely punished for it … Furthermore, I hope for a great success if the plans of the Rebels remain unchanged… I have all the plans of the Rebels and will catch them in their own trap if my men are equal to the emergency…”. In fact, he had already lost 18 hours.

Lee was surprised that the Union army was moving quicker than anticipated.

And by McClellan’s sudden change in tactics after the Union Army arrived in Frederick. When Lee learned sometime after the Maryland Campaign about the lost order he understood the change, saying, “to discover my whereabouts . . . and caused him to act as to force a battle on me before I was ready for it…I would have had all my troops reconcentrated . . . stragglers up, men rested and intended then to attack.”

The importance of finding Order 191 was increased by the delay in the fall of Harpers Ferry. Jackson’s operation in Harpers Ferry was three days behind schedule. If Jackson had been on schedule, the finding of the order would have been of limited value to McClellan. Since Jackson was behind schedule and the operation still active made the order invaluable information. 

Sherman’s March To The Sea

Lee was able to gather some of his corps, hold the passes at South Mountain long enough to converge more of his troops, and concentrate near Sharpsburg MD on Antietam Creek. The Battle of Antietam would be the result. Lee was forced to fight on that ground rather than having the opportunity to choose his own location and time.

So, Who Lost The Order?

To this day, no one really knows. Hill always denied receiving them and his chief of staff did as well, saying that had they arrived at his staff, they would have been handled carefully and with documentation. 

The only other possible culprit would be the courier. Who else would wrap such a critical order in cigars?  Perhaps Chilton always knew who that courier was and wouldn’t say to protect him. 

If that were the case, a very serious candidate would be Henry Kyd Douglas. He was an officer on Jackson’s staff at that time. It’s not a stretch to think he was at Lee’s HQ having just delivered dispatches, and Chilton asked him to drop off a copy on the way past Hill’s encampment.  Whether he lost them or saw that Hill had received the copy and discarded them is speculative. He commanded troops in action later in the war. Douglas wrote a memoir called I Rode With Stonewall, which was highly regarded. He was a very popular speaker and was active in veterans groups. 

Incidentally, he smoked cigars. My conjecture is that he is the man.

The “Lost Order” Of General Lee by Dr Lloyd W Klein

The “Lost Order” Of General Lee by Dr Lloyd W Klein

Further Reading For The “Lost Order” Of General Lee by Dr Lloyd W Klein : 

Sears, Stephen W. (1983). Landscape Turned Red: The Battle of Antietam. Boston: Houghton Mifflin.

https://www.battlefields.org/learn/primary-sources/general-robert-e-lees-lost-order-no-191

https://www.joeryancivilwar.com/Special-Order-191/Ruse-of-War.html

The “Lost Order” Of General Lee by Dr Lloyd W Klein