I’ve been reading a bunch of books about the U.S. Civil War lately and ran across a story that boggles my mind. The history of the so-called “Lost Order” is one of those tales that is so improbable that you couldn’t make it up. On top of that, the Lost Order may well have changed the course of history: but for the Lost Order, the South might well have won, i.e., not lost, the Civil War.
By way of background, as of September 1862, the North was staggering. Particularly in the Eastern Theater (Virginia), the Union had suffered an unbroken series of military defeats, often catastrophic: First Bull Run/Manassas in July 1861; Stonewall Jackson’s Shenandoah Valley campaign in mid-1862; McClellan’s Peninsula Campaign in June-August 1862; and, most recently, Second Bull Run/Second Manassas in August 1862, in which Robert E. Lee had come close to destroying the Union Army of Virginia under John Pope. Mid-term elections were approaching, in which it was feared that Northern disaffection with the war would result in significant victories for anti-war Democrats. England and France were seriously considering whether to recognize the Confederacy, which all concerned recognized would probably be fatal to the Union’s war efforts.
After Second Manassas, the Union army was in utter disarray. In despair, Lincoln relieved General Pope and reappointed George McClellan, whom he had effectively relieved of command after the debacle on the Peninsula. Although McClellan had proved that he was grossly insubordinate and unable or unwilling to fight, Lincoln felt he had no choice. Pope had proved himself incompetent, there were no other suitable candidates, and McClellan was extremely popular in some circles and was at least capable of restoring morale and order in the army.
Second Manassas took place in northern Virginia. Following that battle, Lee took his army north, into Maryland, in the hope that a victory there would destroy the last vestiges of Union resolve and produce election results in November that would compel the North to seek peace. McClellan, prodded by Lincoln, followed half-heartedly at a respectful distance.
On September 9, 1862, General Lee and his army were at Frederick, MD. Contrary to Lee’s expectations, the Federals had not abandoned their depot at Harper’s Ferry, Virginia, which was exposed and now lay to Lee’s rear. On that date, Lee issued an Order (Special Orders No. 191) dividing his army into four parts. Three groups were to approach Harper’s Ferry from different directions, surround it and take it. A fourth part of the army, under General James Longstreet (accompanied by Lee), was to continue the advance into Maryland. Lee’s Adjutant, Robert H. Chilton, wrote out seven copies of the Order, each copy addressed to a specific commander, two of whom were Stonewall Jackson and D.H. Hill. The Order meant that, until the attack on Harper’s Ferry was completed and the army reunited, Lee’s army, which was small to begin with – perhaps 40,000 men – would be divided. Lee felt little concern about dividing his army because he was familiar with McClellan’s timidity and confident that McClellan would not move to attack.
D.H. Hill was, technically, a subordinate of Stonewall Jackson. For this reason, and because Jackson did not realize that Lee had issued a copy of the Order directly to Hill, Jackson also issued a copy of the order to Hill. Hill received (and saved) the copy of the Order he received from Jackson, but the copy addressed to him from Lee was apparently somehow lost.
The Confederate Corps promptly split up and moved out in accordance with the Order. Three groups headed south, by different routes, toward Harper’s Ferry. The fourth group, under James Longstreet, continued into Maryland. Beginning September 12, the Union army moved into Frederick, which the Confederates had vacated. Lee’s assessment of McClellan was entirely accurate. McClellan believed that Lee’s army was far larger than his (when it was, in fact, less than half the size of the Union army). He had little idea where Lee's army was located or headed, and had no idea that Lee had divided his army. He was tagging along well behind Lee and would not attack.
Incredibly, on September 13, a Union soldier stationed on the outskirts of Frederick by chance saw an envelope lying nearby in a field where he was camped. He picked it up and discovered that it contained three cigars, wrapped in a piece of paper. He saw that there was writing on the paper and actually read it, understood that it was important, and turned it over to his superior. Equally incredibly, one of his superiors realized that the document was genuine because he recognized the handwriting – it was the handwriting of Robert Chilton, Lee’s adjutant, whom he knew from before the War. The document was promptly forwarded to McClellan who, upon reading it, immediately understood its importance and exclaimed, “Now I know what to do.” The document was the copy of the Special Orders written by Chilton and addressed to D.H. Hill.
In fact, if McClellan had acted with reasonable promptness, he probably could have caught and destroyed Longstreet’s Corps (and Lee) before the other portions of Lee’s army could reunite with it. McClellan dithered instead. The Lost Order did, however, get him moving, however belatedly and hesitantly. Three days later, on September 16, he confronted Lee by Antietam Creek, near the town of Sharpsburg, Maryland. After delaying for yet another day (allowing the last elements of Lee’s army to reunite), on September 17, McClellan brought on the battle known as Sharpsburg or Antietam.
Antietam was basically a tactical draw. Indeed the North suffered more casualties (12,400) than the South (10,300). However, Lee’s smaller army, devastated by the loss of one-quarter of its force and lacking ammunition and supplies, was forced to retreat back to Virginia (McClellan, of course, mounted no meaningful pursuit), resulting in a strategic and perceived victory for the Union. Based on the result, Lincoln felt emboldened to issue the Emancipation Proclamation, which he had been holding in his drawer since June, waiting for a victory before issuing it. The perceived victory -- the first victory of any sort for Union forces in the East -- and the issuance of the Proclamation, dramatically influenced Northern and international perceptions. The November 1862 elections went reasonably well (far better than they would have gone otherwise), and England and France shelved talk of Southern recognition. Although the North would continue to suffer disastrous defeats thereafter (notably Fredericksburg in December 1862 and Chancellorsville in May 1863), the perceived victory at Antietam allowed the Union to persevere until Lee again invaded the North, and again suffered defeat – at Gettysburg on July 1-3, 1863. Gettysburg, together with the simultaneous surrender of Vicksburg to U.S. Grant , signaled the end of the beginning of the war.
Although responsibility for loss of the Order remains unclear, it now seems probable that Hill was not the culprit. Lee’s Adjutant, Chilton, claimed that he could not recall whether he had received a written receipt confirming delivery to Hill. He also admitted that he did not have documentary evidence of receipt. However, he asserted that he had a procedure by which he required written receipts and that he believed that he would have noticed if he had not received confirmation from Hill.
Both Hill and Hill’s adjutant, on the other hand, always consistently maintained that they never received the copy of the Order from Lee – the only copy of the Order that they received was the one from Jackson. Bolstering Hill’s credibility is the fact that he kept, and later produced from his headquarters files, the copy of the Order from Jackson. As noted, Chilton maintained no documentary evidence supporting his position (such as receipts or a log reflecting receipts). Neither the courier nor the owner of the cigars was ever identified. The best guess therefore seems to be that, however the Order was lost, it never made it to Hill’s headquarters. In the rush of events (the army was splitting up and moving out), Chilton apparently did not notice that he had not received confirmation of receipt.
Books that discuss the Lost Order include Stephen Sears, Landscape Turned Red: The Battle of Antietam, pp. 111-115 and Appendix I; James McPherson, Crossroads of Freedom: Antietam, The Battle that Changed the Course of the Civil War, pp. 107-108; Sears, “The Last Word on the Lost Order”, reprinted in Robert Cowley (ed.), With My Face to the Enemy: Perspectives on the Civil War. A detailed internet article with interesting speculation as to how and by whom the Order was lost appears here.
By way of background, as of September 1862, the North was staggering. Particularly in the Eastern Theater (Virginia), the Union had suffered an unbroken series of military defeats, often catastrophic: First Bull Run/Manassas in July 1861; Stonewall Jackson’s Shenandoah Valley campaign in mid-1862; McClellan’s Peninsula Campaign in June-August 1862; and, most recently, Second Bull Run/Second Manassas in August 1862, in which Robert E. Lee had come close to destroying the Union Army of Virginia under John Pope. Mid-term elections were approaching, in which it was feared that Northern disaffection with the war would result in significant victories for anti-war Democrats. England and France were seriously considering whether to recognize the Confederacy, which all concerned recognized would probably be fatal to the Union’s war efforts.
After Second Manassas, the Union army was in utter disarray. In despair, Lincoln relieved General Pope and reappointed George McClellan, whom he had effectively relieved of command after the debacle on the Peninsula. Although McClellan had proved that he was grossly insubordinate and unable or unwilling to fight, Lincoln felt he had no choice. Pope had proved himself incompetent, there were no other suitable candidates, and McClellan was extremely popular in some circles and was at least capable of restoring morale and order in the army.
Second Manassas took place in northern Virginia. Following that battle, Lee took his army north, into Maryland, in the hope that a victory there would destroy the last vestiges of Union resolve and produce election results in November that would compel the North to seek peace. McClellan, prodded by Lincoln, followed half-heartedly at a respectful distance.
On September 9, 1862, General Lee and his army were at Frederick, MD. Contrary to Lee’s expectations, the Federals had not abandoned their depot at Harper’s Ferry, Virginia, which was exposed and now lay to Lee’s rear. On that date, Lee issued an Order (Special Orders No. 191) dividing his army into four parts. Three groups were to approach Harper’s Ferry from different directions, surround it and take it. A fourth part of the army, under General James Longstreet (accompanied by Lee), was to continue the advance into Maryland. Lee’s Adjutant, Robert H. Chilton, wrote out seven copies of the Order, each copy addressed to a specific commander, two of whom were Stonewall Jackson and D.H. Hill. The Order meant that, until the attack on Harper’s Ferry was completed and the army reunited, Lee’s army, which was small to begin with – perhaps 40,000 men – would be divided. Lee felt little concern about dividing his army because he was familiar with McClellan’s timidity and confident that McClellan would not move to attack.
D.H. Hill was, technically, a subordinate of Stonewall Jackson. For this reason, and because Jackson did not realize that Lee had issued a copy of the Order directly to Hill, Jackson also issued a copy of the order to Hill. Hill received (and saved) the copy of the Order he received from Jackson, but the copy addressed to him from Lee was apparently somehow lost.
The Confederate Corps promptly split up and moved out in accordance with the Order. Three groups headed south, by different routes, toward Harper’s Ferry. The fourth group, under James Longstreet, continued into Maryland. Beginning September 12, the Union army moved into Frederick, which the Confederates had vacated. Lee’s assessment of McClellan was entirely accurate. McClellan believed that Lee’s army was far larger than his (when it was, in fact, less than half the size of the Union army). He had little idea where Lee's army was located or headed, and had no idea that Lee had divided his army. He was tagging along well behind Lee and would not attack.
Incredibly, on September 13, a Union soldier stationed on the outskirts of Frederick by chance saw an envelope lying nearby in a field where he was camped. He picked it up and discovered that it contained three cigars, wrapped in a piece of paper. He saw that there was writing on the paper and actually read it, understood that it was important, and turned it over to his superior. Equally incredibly, one of his superiors realized that the document was genuine because he recognized the handwriting – it was the handwriting of Robert Chilton, Lee’s adjutant, whom he knew from before the War. The document was promptly forwarded to McClellan who, upon reading it, immediately understood its importance and exclaimed, “Now I know what to do.” The document was the copy of the Special Orders written by Chilton and addressed to D.H. Hill.
In fact, if McClellan had acted with reasonable promptness, he probably could have caught and destroyed Longstreet’s Corps (and Lee) before the other portions of Lee’s army could reunite with it. McClellan dithered instead. The Lost Order did, however, get him moving, however belatedly and hesitantly. Three days later, on September 16, he confronted Lee by Antietam Creek, near the town of Sharpsburg, Maryland. After delaying for yet another day (allowing the last elements of Lee’s army to reunite), on September 17, McClellan brought on the battle known as Sharpsburg or Antietam.
Antietam was basically a tactical draw. Indeed the North suffered more casualties (12,400) than the South (10,300). However, Lee’s smaller army, devastated by the loss of one-quarter of its force and lacking ammunition and supplies, was forced to retreat back to Virginia (McClellan, of course, mounted no meaningful pursuit), resulting in a strategic and perceived victory for the Union. Based on the result, Lincoln felt emboldened to issue the Emancipation Proclamation, which he had been holding in his drawer since June, waiting for a victory before issuing it. The perceived victory -- the first victory of any sort for Union forces in the East -- and the issuance of the Proclamation, dramatically influenced Northern and international perceptions. The November 1862 elections went reasonably well (far better than they would have gone otherwise), and England and France shelved talk of Southern recognition. Although the North would continue to suffer disastrous defeats thereafter (notably Fredericksburg in December 1862 and Chancellorsville in May 1863), the perceived victory at Antietam allowed the Union to persevere until Lee again invaded the North, and again suffered defeat – at Gettysburg on July 1-3, 1863. Gettysburg, together with the simultaneous surrender of Vicksburg to U.S. Grant , signaled the end of the beginning of the war.
Although responsibility for loss of the Order remains unclear, it now seems probable that Hill was not the culprit. Lee’s Adjutant, Chilton, claimed that he could not recall whether he had received a written receipt confirming delivery to Hill. He also admitted that he did not have documentary evidence of receipt. However, he asserted that he had a procedure by which he required written receipts and that he believed that he would have noticed if he had not received confirmation from Hill.
Both Hill and Hill’s adjutant, on the other hand, always consistently maintained that they never received the copy of the Order from Lee – the only copy of the Order that they received was the one from Jackson. Bolstering Hill’s credibility is the fact that he kept, and later produced from his headquarters files, the copy of the Order from Jackson. As noted, Chilton maintained no documentary evidence supporting his position (such as receipts or a log reflecting receipts). Neither the courier nor the owner of the cigars was ever identified. The best guess therefore seems to be that, however the Order was lost, it never made it to Hill’s headquarters. In the rush of events (the army was splitting up and moving out), Chilton apparently did not notice that he had not received confirmation of receipt.
Books that discuss the Lost Order include Stephen Sears, Landscape Turned Red: The Battle of Antietam, pp. 111-115 and Appendix I; James McPherson, Crossroads of Freedom: Antietam, The Battle that Changed the Course of the Civil War, pp. 107-108; Sears, “The Last Word on the Lost Order”, reprinted in Robert Cowley (ed.), With My Face to the Enemy: Perspectives on the Civil War. A detailed internet article with interesting speculation as to how and by whom the Order was lost appears here.
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