Lee’s Lost Dispatch

Provided below is a copy of a speech I gave to the Civil War Roundtable of North Florida about the Lost Order of the Antietam Campaign.

The Confederacy never came closer to winning its independence than in September 1862.
Only three months earlier in late June, Washington brimmed with expectations of a Confederate collapse. The first six months of the year provided a string of federal victories in the West. They began in January at Mill Springs, Kentucky and continued with the surrender of 14,000 Rebels at Fort Donelson in February, Confederate ejection from Missouri in March at Pea Ridge, and culminated with the repulse of the supreme Confederate counter-offensive at Shiloh in April. Even a Rebel offensive in remote New Mexico was turned back.

In May the South’s largest city, New Orleans, surrendered to a Union fleet that fought past the city’s downstream fortifications. When Memphis was occupied in early June only a single Rebel outpost at Vicksburg prevented Union commerce from flowing down the Ohio, Mississippi and Missouri rivers to export markets through New Orleans.

Union prospects were also favorable in the East where Major General George McClellan commanded the largest army ever assembled in the Western hemisphere. His troops were so close to the Confederate capital at Richmond, Virginia that they could set their watches by the city’s church bells. He planned to smash the Rebel defenses to rubble once he concentrated siege guns at Old Tavern less than six miles from the city, which he would then take by assault. Unless something unexpected happened, Washington’s optimism seemed justified.

But the unexpected did happen.

In about a week of steady fighting beginning on June 26, Robert E. Lee’s smaller army relentlessly drove McClellan back twenty miles to a defensive redoubt on the James River under the protective guns of the federal navy. Lee’s “trick” was to concentrate superior numbers at the attacking points and to demoralize McClellan with persistent assaults. Once ensconced at the James River stronghold, President Lincoln could not persuade McClellan to resume an offensive without meeting the general’s demands for sizeable, and unavailable, reinforcements.

McClellan’s reluctance to move forward enabled Lee to take the initiative and attack a second federal army in northern Virginia, which he routed at the Second Battle of Bull Run on August 30. During a postscript battle at Chantilly the next day in a failed attempt to cut off the enemy’s retreat to Washington, Lee’s men came within twenty miles of the White House. In two months the battlefront switched from the doorstep of the Confederate capital to the front yard of the US capital.

Washington was panicked. President Lincoln told Attorney General Edward Bates that he felt “almost ready to hang himself.” Secretary of War Edwin Stanton considered the city lost and ordered that a steamer be kept ready to evacuate the cabinet and the president.
By late August Confederate armies in the West were also on the offensive. On the same day Lee won at Second Bull Run a smaller Rebel army smashed an opposing 6,000-man Yankee force at Richmond, Kentucky by killing, wounding, or capturing over 5,000 of them. About two weeks later another prong of the Kentucky offensive captured a 4,000-man federal garrison at Munfordville. Cincinnati was nearly as rattled as Washington.

During the previous year or so Europeans were starved for cotton. They were less concerned with which side won the war than that it be quickly ended in order to restore the flow of cotton presently blockaded. Great Britain had the world’s mightiest economy and cotton textiles represented about 20% of it.

In mid-September the British Prime Minister wrote his Foreign Secretary –equivalent to our Secretary of State – suggesting that the cabinet consider intervention. The secretary replied, “the time has come for offering mediation…with a view to recognition…of the Confederates. In case of failure…we ought to ourselves recognize the Southern state.” There it was; a proposal for Confederate diplomatic recognition that could put Great Britain at war with the United States. France would likely follow Great Britain.

General Lee and Confederate President Jefferson Davis reasoned that another decisive victory against the chief eastern Union army – north of the Potomac River on federal soil this time – could win Confederate independence for two reasons. First, it might trigger Northerners into losing the willpower to prevent secession. The Yankees could have peace merely by letting the Southern states depart. Second, it could further encourage Britain and France to side with the Confederacy. Much as France helped thirteen colonies gain liberty in the American Revolution, eighty-six years later the two mightiest European powers could help the Confederates win independence.

Maryland_Campaign copy

Map by Hal Jespersen cwmaps.com

On September 8, only about a week after his Bull Run victory, Lee was concentrating his army at Frederick, Maryland, about forty miles northwest of Washington. His army numbered about 40,000, excluding around 15,000 stragglers that resulted from the blistering marching pace set by the commander in order to hold the strategic initiative. His chief opponent, General McClellan, had 85,000 troops, and an additional 72,500 were defending Washington under Major General Nathaniel Banks. Lee knew Washington fortifications were too strong to attack, but he hoped to lure McClellan into the open, for a fight to the finish north of the Potomac.

McClellan entered the campaign with two handicaps. First, he persistently overestimated the size of Lee’s army. Second, Radical Republican politicians in his rear were among his worst enemies.

When McClellan was originally given command of the Union’s largest army thirteen months earlier, he hired Chicago detective Allan Pinkerton to organize a systematic intelligence network. Although Pinkerton’s methodical reports were authoritative looking they enormously overestimated the size of opposing forces. Thus, when McClellan later captured one of Lee’s orders that identified each Rebel unit, he falsely believed that each Confederate army unit was three times larger than comparable ones in the Union army.

Major General John Pope, who was a favorite of the Radical Republicans, led the Union army routed at Second Bull Run. Since the Radicals applauded his stern treatment of Southern civilians they searched for a culprit to explain Pope’s defeat. They settled on McClellan whom they accused of deliberately withholding reinforcements to Pope’s army.

War Secretary Stanton and Treasury Secretary Chase wrote a condemnation of McClellan, which four of seven cabinet members signed. It was essentially a threat to break up the administration unless Lincoln cashiered McClellan. But before they could present it at a cabinet meeting, Lincoln gave McClellan “command of the fortifications of Washington and all the troops for the defense of the capital.” When he later met with his cabinet, Lincoln implied that McClellan’s selection was only temporary.

Although placating the Radicals, Lincoln’s implication revealed an underlying weakness in the federal command. Specifically, McClellan could not be confident of his authority once he took troops out of Washington. For example, as he moved to challenge Lee he was unsure whether he might draw reinforcements from garrisons such as Harpers Ferry and Washington.

Lee’s problem was to draw part of the Union army out of Washington for an open fight before the Yankees had a chance to recover from the low morale resulting from the recent string of defeats. He could beat a bigger army if it was demoralized, but each day the enemy was given time to recover its confidence lengthened the odds against him. Lee decided to cut the Union’s east-west communications by destroying a Maryland canal and key railroads in Maryland and Pennsylvania. If done quickly such action might compel the federal army to leave its impregnable Washington defenses before their morale had recovered.

But first Lee needed to clear an invasion path into Pennsylvania by eliminating isolated Union forces in the Shenandoah and Cumberland valleys. Among them were 13,000 federals at, or near, Harpers Ferry. On September 9, Lee gathered with his two wing commanders, Major Generals Thomas “Stonewall” Jackson and James Longstreet, to devise a plan. The result became Special Order No. 191.

Lost Dispatch Map copy 2The order directed that Lee’s army be divided into two parts. On September 10 Jackson got two-thirds of it to capture Harpers Ferry eighteen miles to the southwest. Lee was to take the remaining one-third under Longstreet fourteen miles northwest to Boonsboro, Maryland, on the west side of South Mountain. However, once underway, Lee continued ten more miles to Hagerstown just shy of the Pennsylvania line due to reports that Rebel supplies in the town were threatened. Upon arriving at their respective destinations, the two components of the army were separated by twenty-five miles on a north-south axis. Major General Daniel Harvey (D. H.) Hill’s division was to be the rearguard between the two on the west side of South Mountain.

Jackson’s command was further divided into three segments corresponding to the triangular perimeter of Harpers Ferry formed by the conjunction of the Potomac and Shenandoah rivers. If Lee or any of Jackson’s segments required help, each fragment would face at least one difficult river crossing in order to render aid. In sum, Lee’s smaller army would be temporarily divided into five fragments. If informed of Lee’s deployment, McClellan could almost certainly overwhelm the pieces separately. But Lee anticipated the vulnerability would be brief because he expected Harpers Ferry to fall by September 12.

On September 13, McClellan’s army marched into Frederick, which was only fifteen miles east of the midpoint in the north-south line separating Lee from Jackson. Sometime before or around noon, a Union solider found a bulky envelope at a former Rebel campsite. Inside was an official-looking paper wrapped around three cigars. The document concluded “By command of General Robert E. Lee” and was signed “R. H. Chilton, Assistant Adjutant General.” It was quickly passed up to a corps commander who included Colonel Samuel Pitman among his staff officers. Before the war, Pitman worked at a Detroit bank, where he frequently paid drafts with Chilton’s signature because Chilton was paymaster at a nearby army post. Pitman verified that the captured copy of Special Order 191 was authentic.

It was soon given to McClellan while he was meeting with a group of local citizens. He quickly dismissed the group and wired Lincoln, “I have all the Rebel plans and will catch them in their own trap.”

A Confederate sympathizer was among the citizens meeting with McClellan when the order arrived. Although he did not know the specifics, he could judge from McClellan’s reaction that the federals had unexpectedly learned something significant. The unknown Rebel eventually passed the news along an intelligence chain that reached to Lee.

Upon examining the order, McClellan decided that the two most vulnerable components of Lee’s army were (1) the command of Major General Lafayette McLaws besieging Harpers Ferry from Maryland Heights and (2) Longstreet’s truncated wing, presumed to be at Boonsboro based on the Lost Dispatch. McLaws had about 8,000 men while Longstreet had about 12,500 men.

McClellan instructed Major General William Franklin to attack McLaws with his 13,000-man corps on the morning of September 14. Franklin would march through Crampton’s Gap of South Mountain and assault McLaws from the north while the Confederates faced south toward Harper’s Ferry. But Franklin did not attack the gap until mid–afternoon, despite having a fifteen-to-one numerical advantage over the few defenders McLaws sent to guard the gap. Essentially, September 14 was a wasted opportunity in Franklin’s sector. But if the Union defenders at Harpers Ferry could hold out another day, Franklin would have a second chance on September 15 because McLaws would still be trapped between Franklin in his rear and a combination of the Potomac River and the Harpers Ferry garrison to his front.

Meanwhile, not realizing that Lee sensed something amiss, McClellan expected that Longstreet’s truncated wing and Hill’s rearguard would be together at Boonsboro as indicated in the Lost Dispatch. Thus, he expected only light cavalry resistance at the intervening South Mountain gaps before descending upon Longstreet and Hill with an overwhelming force of 65,000 Union veterans.

But on the night of September 13–14, Lee responded to the warning given by the sympathetic Frederick resident. He instructed Longstreet to return to Boonsboro from Hagerstown and directed that Hill defend Fox and Turner’s gaps, which were the mountain passes that McClellan would need to pierce in order to get between Jackson and Lee. Thus, on the morning of September 14 McClellan met Hill’s rearguard instead of mere cavalry when he tried to force his way through the gaps. Despite being outnumbered six-to-one, Hill blocked the federals until nightfall partly because McClellan characteristically overestimated the size of the enemy force.

Thus, in addition to Franklin’s failure to overwhelm McLaws, McClellan’s efforts to get at Longstreet were thwarted. Although the federals won tactical victories at the South Mountain passes, they failed to either destroy McLaws’s isolated command or get their 85,000-man army between Lee’s 14,000 and Jackson’s 26,000. Nonetheless, Lee’s army remained scattered and vulnerable.

By nightfall September 14 Lee realized that McClellan’s discovery of an unknown Confederate order made the Union commander uncharacteristically aggressive. He immediately perceived that McLaws was most vulnerable. At 8:00 PM he sent couriers to Jackson and McLaws, directing that they abandon the Harpers Ferry siege and ordered the Maryland components of the Army of Northern Virginia to concentrate at Sharpsburg in preparation for crossing the Potomac River ford at Shepherdstown where all would combine with Jackson on the Virginia side. McLaws attempted to reply with several couriers, but none got through. Nonetheless, he did not believe that he could escape and decided to defend his position against a likely renewal of Franklin’s attack on his rear the next morning.

Initially, Lee decided to move Longstreet and Hill only part way to Sharpsburg, to a place where they could protect McLaws’s flank. But when Jackson replied that he believed the Harpers Ferry garrison would surrender the next morning, Lee told Hill and Longstreet to proceed to Sharpsburg and deploy defensively behind Antietam Creek. If Jackson and McLaws forced Harpers Ferry to surrender, Lee would concentrate his reunited army at Sharpsburg to battle McClellan’s entire army on Maryland soil.

As Jackson predicted, Harpers Ferry capitulated the following morning, September 15. When Union General Franklin heard cheering from the Rebel lines he decided against renewing his attack of the preceding day, falsely believing McLaws outnumbered him. At sundown, Lee had 15,000 Confederates deployed in a battle line near Sharpsburg. As McClellan examined them through field glasses, he already had four times their number on the scene.

Due to morning fog, McClellan declined to attack at Antietam the next day, September 16. Lee’s army gained strength to 27,000 as reinforcements arrived from Harpers Ferry. McClellan finally attacked at first light on September 17 triggering the Battle of Antietam that became the bloodiest single day of the Civil War. McClellan had 72,000 troops on hand, whereas Lee had fewer than 35,000 until late in the afternoon. By nightfall, McClellan suffered 12,400 casualties, while inflicting 10,300. The armies glared at one another the following day before Lee withdrew to Virginia on September 19. McClellan is generally faulted for failing to use his superior numbers effectively. Instead he attacked different segments of the Rebel line sequentially, thereby enabling Lee to rush reinforcements to threatened points from units that were temporarily idle.

Although historians know how Special Order 191 was discovered and authenticated it is not known how it got lost, or perhaps even stolen.

Three copies survive. One was delivered to Richmond and now is in the National Archives. A second addressed to D. H. Hill is in Stonewall Jackson’s handwriting and was held by Hill until his death in 1889. It is presently in the North Carolina State Archives. A third copy, also addressed to Hill, originated in Lee’s headquarters and was the one found by the Union soldier. The third copy is in the Library of Congress.

Hill was sent two copies because of his ambiguous reporting status. His division was a late reinforcement to the campaign and upon arrival reported to Lee. Before Lee crossed the Potomac, Jackson was the senior commander on the river’s north bank and Hill reported to him after the latter crossed to the left bank. But once Lee arrived on the left bank, Hill was once again expected to report to Lee.

As noted, Special Order 191 was written at Frederick on September 9. Colonel Chilton, who was Lee’s adjutant, signed the copies for delivery to the seven generals designated in the order: Jackson, Longstreet, D. H. Hill, McLaws, John Walker, J. E. B. Stuart, and William Pendleton, who commanded the artillery reserve. Brigadier General Walker was included because his division formed the third side of the planned triangle to surround Harpers Ferry, while the other two sides were to be formed by the commands of McLaws and Jackson.

Hill was among the recipients designated by Chilton because his division was to act independently as a rearguard. However, when Jackson received his copy, he wrote a second copy for Hill, presumably because he felt that Hill’s division remained part of his command. The confusion was tragic because Hill claimed his brother-in-law Jackson’s copy was the only one he ever received and the other one addressed to Hill from Lee was the one that fell into enemy hands.

Over the years, Hill went to great trouble to document that it was not his fault that Union soldiers captured one of the copies addressed to him. After the war, his chief of staff swore an affidavit stating the dispatch from Lee’s headquarters never arrived. Similarly, in postwar correspondence with McClellan, Hill learned that the Lost Dispatch was found inside an envelope, which Hill presumed was the one it was delivered in. He also obtained letters from two former Union officers stating that the Lost Dispatch was found two miles from Hill’s campsite. But even if the order were discovered miles away, it could have been dropped as Hill’s unit marched out of Frederick the next day.

Confederate leaders were only certain about the identity of the captured document six months later, when McClellan testified before Congress in March 1863. Partly because of the delay, Lee never had a formal investigation, although General Stuart and other officers became indignant with Hill when they learned his name was on the captured copy.

It seems logical that Chilton, Hill, or their staffs were likely responsible for losing the copy from Lee to Hill. Since it was half a year before Chilton learned which dispatch copy was lost, he claimed he could not recall the name of the selected courier. Although he did not maintain a log of couriers chosen and receipts returned, upon inquiry from Jefferson Davis after the war, he replied that failure to receive a receipt would undoubtedly have prompted a follow up. Yet nobody from Hill’s staff admitted signing one.

At one point Hill suggested the variances between his and Chilton’s accounts could be reconciled if the courier were a spy. But it seems implausible that a spy would leave the order in an open field where it might only be discovered by accident.

Since it was customary for delivery envelopes to also function as stock for signed receipts, some historians argue that the discovery of the order inside an envelope is convincing evidence that the copy from Chilton never reached Hill. But that scenario has problems.
For one thing, there’s no evidence the envelope was sealed when discovered. In fact the finder’s first sergeant claimed it was discovered unsealed. Yet the order was probably originally sealed so it could not easily be secretly examined and replaced by unauthorized readers. Moreover, it is unlikely Chilton would have wrapped the order around three cigars before sealing it in an envelope.

The differing Chilton and Hill accounts cannot be reconciled. But if responsibility for losing Lee’s order can’t be affixed to one officer or the other, it remains possible, at least circumstantially, that they share the blame. Both men had other incidents of bad judgment and unwillingness to accept the consequences of their actions.

Just before the Battle of Chickamauga the following year, Hill was at least partly responsible for the lost opportunity at McLemore’s Cove. His commander, General Braxton Bragg, had set one of the best traps of the war to crush an isolated Yankee division, but Hill failed to attack as ordered. Similarly, Chilton prepared and delivered ambiguous orders during the Peninsula Campaign and the Battle of Chancellorsville.

Ultimately it seems likely the Lost Dispatch was an unlucky consequence of a statistically predictable increase in the probability of errors resulting from Lee’s hurried movements following Second Bull Run. In order to hold the initiative, his marches challenged the hardiest soldiers to keep up. Many simply could not. Straggling became epidemic. Evidently, administrative officers were also hard pressed to keep up with demands.
Perhaps when Chilton’s courier arrived, he learned that Hill had already received the orders and assumed his copy was merely a duplicate. With no need to leave the orders and believing them to be superfluous he may simply have obtained a perfunctory receipt and kept the envelope and enclosure to hold his own cigars. It is the sort of thing anyone might do, and if he were one of the 1,500 Rebels killed at Antietam, his story would never be heard.

Alternatively, upon realizing his copy was lost, a surviving culprit may have felt too ashamed or fearful of punishment to reveal his guilt. A tale about Robert E. Lee famously repeated in the PBS Civil War film documentary illustrates the point:

“Once a soldier was brought before Lee for a rule infraction. The young man was trembling and Lee said, ‘You need not be afraid. You’ll get justice here.’ And the young man said, ‘I know it general, that’s what I’m scared of.’

Only the ghosts of those involved know the truth of how the Lost Dispatch was misplaced. But given burgeoning access to historical information on the Internet, more theories are surfacing. Perhaps one of you shall discover the truth.

Gainesville, Florida…July 9, 2015…Philip Leigh

If you liked the narrative above consider buying one of my books.

Lee’s Lost Dispatch and Other Civil War Controversies
Trading With the Enemy
Co. Aytch: Illustrated and Annotated


2 thoughts on “Lee’s Lost Dispatch

  1. monaeagle

    Enjoyed the read. My family is from Central WV. I was raised in the Eastern Panhandle and now live back in Central. The Civil War is very intriguing to me. Thanks for sharing.


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