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October 20, 2016

Why Lee’s Lost Orders Were Less Important Than We Think: A Counter-Factual Analysis.

This piece explores what might have been had Lee’s Special Orders No. 191 not been lost and recovered by Army of the Potomac commander, General George B. McClellan. The argument put forward is that Lee’s freedom of movement was more constrained in September 1862 by his own orders than by anything McClellan did. So constrained were Lee’s choices, in fact, that there could never have been a major battle fought in Pennsylvania that month. Any major engagement was bound by a lack of alternatives to take place in Washington County, Maryland or Jefferson County, (West) Virginia. 

The loss of General Robert E. Lee’s Special Orders No. 191 near Frederick, Maryland is often considered an important turning point in the history of the American Civil War. After an errant copy of the orders fell into Major General George B. McClellan’s hands around noon on September 13, 1862, the Union commander pushed heavy columns toward South Mountain. Lee responded by fighting a fruitless rear-guard action at the gaps, after which his portion of the Army of Northern Virginia retreated toward the Potomac before turning to fight again at Sharpsburg. In due course, the Union victory at Antietam forced Lee’s army to withdraw from Maryland, providing President Lincoln with the opportunity to announce a preliminary policy of emancipation on September 22, 1862. Lincoln’s proclamation effectively recast the war as a struggle over slavery, which neutralized the potential involvement of Great Britain and France and ultimately sealed the South’s fate.

Typically, McClellan’s receipt of Lee’s orders is given pride of place in this sequence of events, but is its importance warranted? Learning Lee’s plans undoubtedly gave the Union commander confidence that he had lacked up to that point, but beyond the jolt of backbone were there other lasting effects that rendered the loss of Lee’s orders the campaign’s pivotal non-combat event? Put differently, had the orders not been lost, would the course of Lee’s campaign in Maryland been substantially different?

what-ifThis question prompted the noted Civil War scholar, James M. McPherson, to pen an essay some years ago entitled, “If the Lost Orders Hadn’t Been Lost: Robert E. Lee Humbles the Union, 1862.” McPherson’s piece appeared in a volume of essays assembled by Robert Cowley that examined counter-factual questions throughout 2,000 years of military history. “What If?” the title of the compilation asked; “The World’s Foremost Military Historians Imagine What Might Have Been.”[i]

What might have been, indeed? McPherson’s essay paints a scenario in which Lee’s army enters southern Pennsylvania with McClellan’s Army of the Potomac shadowing it to the east of South Mountain. After some maneuvering, the armies clash at Gettysburg in early October 1862 along lines roughly similar to the battle actually fought in July 1863. This time, however, it is Lee’s troops who emerge victorious. The defeat forces Lincoln to negotiate an end to the war, achieving the South’s independence and allowing Robert E. Lee to return home as the latter-day George Washington that he had long desired to be.

McPherson tells a good story, but the sequence of events it describes is unconvincing because it fails to take into account the circumstances beyond Lee’s control that shaped his decisions during the Maryland Campaign. To be truly effective counter-factual analysis cannot simply describe a new course of events. It must take into account the conditions of the time and place to suggest only those events that were within the realm of possibility. Keeping this in mind, it is highly improbable that Lee’s campaign in Maryland could have ended with a battle in Pennsylvania, especially at a place as far removed as Gettysburg. The fact of the matter is that with the distribution of Special Orders No. 191 on September 10th, Lee himself set in motion events that dictated his own actions for at least the next full week, no matter what George McClellan did.

Consider the following. Like every commander in any conflict, Lee operated under conditions that were beyond his ability to influence. When Colonel Dixon Miles chose not to evacuate the federal garrison at Harper’s Ferry after the Army of Northern Virginia had moved into Maryland it complicated Lee’s plans enormously. Accordingly, Lee devised his special orders to capture Harper’s Ferry, sending Thomas J. “Stonewall” Jackson’s command, along with the divisions of John Walker, Lafayette McLaws, and Richard Anderson, to accomplish the obsouth-mountainjective.[ii]

By September 13th, the Ferry operation had fallen behind schedule, requiring that Lee maintain a defensive presence on South Mountain to ensure Jackson’s success. Therefore,  even though McClellan possessed a copy of Lee’s orders by noon on the 13th, the slow pace of Jackson’s operation required that the Union commander do nothing to pin Lee’s forces where Special Orders No. 191 had placed them.[iii] Furthermore, even after Miles surrendered to Jackson on September 15th, the need to parole captured Northern troops, inventory materiel, and transfer McLaws’ command back to Virginia through the narrow, crowded streets of Harper’s Ferry demanded the protection of McLaws’ rear for at least another full day. As McLaws himself noted in his after-action report, “the crossing at Harper’s Ferry was very much impeded by the paroled prisoners passing over the bridge. Whenever there was an opportunity offered by any accident to the bridge causing [a] temporary halt in the trains or batteries, which was of frequent occurrence, the streets of Harper’s Ferry town were crowded with prisoners and wagons.”[iv] In short, there was no choice for Lee’s rear-guard at South Mountain. It had to remain in place until at least the 16th of September, even if McClellan made no moves.

Now consider the “what if” scenario from the 16th onward. Even from that date the passing of several more days without a Union advance would not have given Lee the latitude he needed to re-unite his army near Hagerstown. One-and-a-half to two days of hard marching separated Jackson’s command from Lee and McLaws’ command in Pleasant Valley had even farther to go. Thus once more Lee’s rear-guard at Boonsboro would have been compelled to stand its ground to buy time for Jackson and McLaws to re-enter Maryland. This time, however, they would have farther to march than Sharpsburg. The one part of Lee’s army that conceivably could have moved out on the 17th is J.E.B. Stuart’s command at Crampton’s Gap, but, like D.H. Hill’s division at Boonsboro, Stuart probably would have been required to stay put until McLaws was safely away.

As for McClellan’s role in all of this, he had already decided to rescue Harper’s Ferry on September 12th, one day before Lee’s orders came into his possession. “The next trouble is to save the garrison of Harper’s Ferry, which is, I fear, in danger of being captured by the rebels,” he wrote to his wife on that day. “If they are not taken by this time I think I can save them; at all events, nothing in my power shall be left undone to accomplish this result.”[v] General-in-Chief Halleck placed Colonel Miles’ command under McClellan on September 12th and Jackson’s bombardment of Harpers Ferry commenced on September 14th. A brigade of Sixth Corps troops under the command of Colonel William Irwin entered Jefferson, Maryland on the route to Harper’s Ferry before 3 p.m. on September 13th, and it is reasonable to assume that McClellan would have continued pushing this column toward Crampton’s Gap on the 14th in response to Jackson’s cannonade. These men, however, would not have gotten far when the guns fell silent, leading Major General William B. Franklin, commander of the Sixth Corps, to pause and ask McClellan for guidance, something he actually did in the historical situation.[vi] In effect, the proximity of Alfred Pleasonton’s cavalry west of Middletown and Franklin’s command on route to Crampton’s Gap would have posed just enough of a threat to necessitate that Lee leave Hill’s and Stuart’s commands in

This brings us to the critical day of Wednesday, September 17th. Up to this time, the confines of Special Orders No. 191, the looming presence of McClellan’s army, and geography dictated the positioning of Lee’s forces. Now, though, the evolving situation would become more fluid. Would the silence from Harpers Ferry have finally compelled McClellan to attack the South Mountain gaps, or would he have sat tight waiting for the situation to develop? It is at moments like these that the character of a man shapes events. McClellan’s character was cautious and he believed a rebel army of up to 120,000 men waited just over the mountain, so he almost certainly would have hesitated to gather more information using local informants and his cavalry.

Taking into account McClellan’s timidity, a new sequence of events can be posed with a comfortable level of plausibility. Federal reconnaissance would have crept closer to Southern lines at Turner’s Gap until it discovered on the rainy afternoon of the 18th that those lines had been abandoned. After all, with the Harpers Ferry operation complete, Lee would have at last had the freedom to withdraw his rear-guard and prepare for battle in central Washington County, Maryland.

Why would Lee have not gone further north as General John Walker later claimed the Southern commander had told him that he would on September 9th? Because pushing north was not an option at that point. Not only was there no need for Lee to move in that direction, he had also run out of time. McClellan’s army had easy access to all of the gaps, including the now undefended passage at Harpers Ferry, which gave him a direct route to Winchester and Confederate supply lines. McClellan was slow, but he was no fool. Already on September 12th he had considered sliding in behind Lee’s army, writing, “I am beginning to think he [Lee] is making off to get out of the scrape by recrossing the river at Williamsport, in which case my only chance of bagging him will be to cross lower down and cut into his communications near Winchester.”[vii]

Given the proximity of the Union army, therefore, moving north was clearly out of the question. It would have further removed Lee’s troops from Winchester and it would have uncovered the critical river crossing at Williamsport. Too much time had been consumed by Jackson’s operation against Harpers Ferry, meaning Lee would need to fight in Maryland, as he later admitted had always been his intention.[viii] The last remaining question was where? One answer is the heights above Beaver Creek, some 4 miles north of Boonsboro. Another possibility was along the west side of Antietam Creek on the axis from Downsville to Williamsport. Either location would have provided an excellent position for the Confederate commander to gather his strength.

Thus, it is highly possible that cockcrow on September 19th would have dawned with the indigo columns of the Army of the Potomac streaming over the gaps in South Mountain. As they descended into Boonsboro, Union scouts riding ahead would have located Confederate forces arrayed in line of battle somewhere to the north-northwest of the town. Observers sent to the pinnacle of the Washington Monument above Boonsboro would have also confirmed the rebel army’s position, signaling to McClellan that the moment of truth had arrived. General Lee invited attack in Washington County, but in accordance with his timid nature, McClellan would not be rushed into action. Another 24 to 48 hours would have passed while blue-coated patrols probed Lee’s lines for a weakness. This was time that Lee would have needed for McLaws and A.P. Hill to finally come up from Harpers Ferry.

The stage would have at last been set by September 21st. With Lee’s army united and McClellan’s force in place, the fighting would have begun in earnest and an unnamed clash that could have easily taken place would have entered the lexicon as the bloodiest day in American history. Had McClellan not come to possess Lee’s orders it is almost certain there would not have been a battle at Turner’s Gap, but what of it? The fight at South Mountain was not decisive. It forced Lee to shift his position toward Virginia until he stopped at Sharpsburg, but in the end even this did not conflict with his intent. The fact remains that Robert E. Lee had planned from the beginning to give battle in Maryland, no matter where the fight took place. In this sense, the lost orders meant little. Even had the orders not been lost Lee’s campaign in the Old Line State would still have ended exactly the way he wanted it to end, with a terrible battle fought in Maryland at a location that he himself had selected.

[i] James M. McPherson, “If the Lost Orders Hadn’t Been Lost: Robert E. Lee Humbles the Union,” in Robert Cowley (ed.), What If? The World’s Foremost Military Historians Imagine What Might Have Been (NY, NY: G.P. Putnam’s Sons, 1999) pp. 223-238.

[ii] For a detailed discussion and analysis of Lee’s orders see Joseph L. Harsh, Taken at the Flood: Robert E. Lee and Confederate Strategy in the Maryland Campaign of 1862 (Kent, Ohio: The Kent State University Press, 1999), pp. 145ff.

[iii] McClellan’s dispatch to President Lincoln, sent at “12 Meridian” on September 13, 1862, indicates that the Union commander already had Lee’s in his possession as of midday. See U.S. War Department, The War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies, 128 vols. (Washington, DC: GPO, 1880-1901), Series 1, Volume 19, Part II, p. 281. Cited hereafter as OR.

[iv] Report of Lafayette McLaws to James Longstreet, October 20, 1862 in OR, Vol. 19, Part I, p. 857.

[v] George B. McClellan, McClellan’s Own Story: The War for the Union (New York, NY: Charles L. Webster & Company, p. 570.

[vi] Dispatch of Franklin to McClellan, September 15, 1862 in OR, Vol. 19, Part I, p. 47.

[vii] McClellan, McClellan’s Own Story, p. 570.

[viii] Lee comments to Colonel William Allan, October 1868, reprinted in Douglas S. Freeman, Lee’s Lieutenants: Cedar Mountain to Chancellorsville, vol. 2 (New York, NY: Charles Scribner’s Sons, 1943), p. 717.


October 7, 2016

September 13, 1862: A Foreshadowing of J.E.B. Stuart’s Gettysburg Failure to Come?

This article appeared on the Emerging Civil War blog October 6, 2016.

Major General James Ewell Brown (J.E.B.) Stuart has been justly criticized for his role in allowing the fateful clash at Gettysburg to occur when neither General Robert E. Lee nor the Army of Northern Virginia were properly prepared. Students of the American Civil War know the story well. While conducting yet another glorious ride around the Federal army, Stuart strayed far from Lee, leaving him blind to the enemy’s movements. Elements of the Army of Northern Virginia seeking a supply of shoes then stumbled into the Federals at Gettysburg, initiating a battle that Lee had not planned to fight. Afterward, Stuart arrived on the field so late that his troopers could not significantly contribute to the outcome of the battle.

These events are well known. Less well known is the fact that Stuart’s botched mission in Pennsylvania was not the first time he had been found wanting during a large-scale operation. The first time Stuart manifestly failed to alert Lee to approaching danger actually occurred in Maryland nine months earlier when on Saturday, September 13, 1862, Stuart’s command abandoned its defensive line on the Catoctin Mountains near Frederick and fell back to South Mountain. The fighting erupted that morning when Federal cavalry engaged Stuart’s troopers at Hagan’s Gap. For eight hours, Stuart’s command fought a valiant defensive action against growing numbers of Federal troops, including elements of Ambrose Burnside’s Ninth Corps, thereby fulfilling a wish expressed by Lee on the 12th that the cavalry “not retire too fast before the enemy.”[1] Despite the period of prolonged combat, however, Stuart claimed in his after-action report to have remained ignorant of the enemy’s strength, saying he wrote to Lee around 2:00 p.m. that, “the enemy was held in check until he had marched up to the attack two brigades of infantry, which was the only force we were yet able to discover, so well did he keep his troops concealed.”[2]


The claim that his command faced only a minor force of infantry and cavalry would be a consistent element of Stuart’s reports to Lee that day and a misleading fact that would lull Lee into thinking McClellan’s army posed no immediate danger. Stuart’s sloppy intelligence gathering along these lines had actually begun days earlier. Per historian Joseph Harsh, “nothing indicates Stuart on [September] 9th perceived the Army of the Potomac to be pressing in a menacing way,” leading Lee to believe his command had plenty of time to carry out Special Orders No. 191 to capture Harpers Ferry.[3] Similarly, after the Union army entered Frederick on September 12th, Stuart informed Lee that the town had fallen, but he did not report the enemy’s strength, writing, “Every means was taken to ascertain … the nature of the enemy’s movement … whether a reconnaissance … or an aggressive movement of the army. The enemy studiously avoided displaying any force, except a part of Burnside’s corps, and built no camp-fires in their halt at Frederick that night.”[4]

Compare Stuart’s claim to the recollection of his staff officer, Major Heros von Borcke, who wrote after the war: “[On the 13th] it was evident that our small body of men would be soon obliged to give way before overwhelming odds [as] the valley beneath [Hagan’s Gap] … was literally blue with the Yankees. All at once their long columns of infantry with a waving glitter of bayonets, their numerous bodies of cavalry with many a flirt and flutter of gay flags and pennons, their imposing artillery-trains with the sunlight reflected from the polished brass pieces, and their interminable lines of wagons.”[5] If von Borcke is to be believed, Stuart’s command faced more than a smattering of Federal cavalry and infantry, yet the dashing cavalier failed to report this to Lee. What accounts for Stuart’s lack of information? John Michael Priest suggests the cause was carelessness, explaining that during the fight at Hagan’s Gap, “Stuart never rode beyond the wooded crest of the mountain” to see the enemy for himself.[6]

Priest may be correct about the action at Hagan’s Gap, but that episode of negligence was only one of Stuart’s missteps. After falling back from the Catoctins, his troopers assumed a new defensive position in front of Middletown. Federal troops took up the pursuit, with Pleasonton’s cavalry in the van and General Issac P. Rodman’s two-brigade infantry division bringing up the rear. Again, Southern defenders were soon overmatched and forced to fall back behind Catoctin Creek. Stuart reported neither this retrograde movement nor the loss of Catoctin Mountain to headquarters despite the fact that giving up Middletown placed Federal troops at the doorstep of General Daniel Harvey Hill’s rearguard at Turner’s Gap.

Why did Stuart not report the looming threat in the east? It appears he labored under the misperception that only cavalry and two brigades of infantry pursued him, not the entire Ninth Corps of McClellan’s army. As George Grattan, a former lieutenant on Colonel Alfred Colquitt’s staff, and one of the first people to meet Stuart atop South Mountain late in the day on September 13th wrote after the war, “General Stuart reported that there were no troops following him but cavalry and that Colonel Colquitt would have no difficulty in holding the pass with his brigade.”[7] D.H. Hill wrote similarly, “Major-General Stuart reported to me … two brigades only of the Yankees were pursuing us, and that one brigade would be sufficient to hold the pass.”[8]

Was Stuart’s misperception warranted? Did Burnside somehow hide the advance of his corps from Confederate eyes? Not according to the evidence. Stuart wrote after the campaign that upon falling back to Middletown, “the enemy soon appeared in force crossing the mountain.” The phrase “in force” is ambiguous, but it suggests Stuart’s reports to Lee ought to have contained a sense of urgency that they did not. Again, compare what Stuart wrote to what Heros von Borcke says he witnessed: “Near Middletown we took up a new position. … General Stuart and myself rode forward a short distance in the direction of the enemy, whom we saw winding down from the mountain and stretching out over the plain in a mighty moving mass of blue.” Von Borcke places Stuart by his side witnessing the Federal advance. Was von Borcke’s recollection simple hyperbole? Perhaps, but it is difficult to conclude this given the other reports that a vast number of campfires appeared below South Mountain as night fell.

Based on the evidence, the inescapable conclusion is this. The advance of McClellan’s army to Middletown on September 13th posed a mortal threat to the Army of Northern Virginia for which Lee was ill-prepared. Had Jeb Stuart reported to Lee earlier in the day that his command faced a large enemy force and not just cavalry and two brigades of infantry, Lee would have had time to move Longstreet’s command back to Boonsboro before the outbreak of fighting on September 14th. One source tells us that members of Stuart’s staff, accompanied by the general himself, witnessed the movement of a powerful Federal force toward South Mountain. Stuart failed to report this movement to Lee, ensuring that his commander would be caught by surprise when news of the enemy threat finally did reach him late in the evening on September 13th. Thus, Lee’s surprise had far more to do with the failure of his cavalry commander to keep him properly informed than it did with McClellan’s discovery of the Lost Orders. It was an operational failure that foreshadowed equally damaging missteps Jeb Stuart would make in Pennsylvania in 1863 with equally dire consequences for Lee and the Army of Northern Virginia.

[1] Lee to Stuart, September 12, 1862 in Joseph L. Harsh, Taken at the Flood: Robert E. Lee and Confederate Strategy in the Maryland Campaign of 1862 (Kent, OH; The Kent State University Press, 1999), p. 197.

[2] Report of Maj. Gen. J.E.B. Stuart, C.S.A. Army, commanding cavalry of operations September 2-20, February 23, 1864 in U.S. War Department, The War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies, 128 vols. (Washington, DC: GPO, 1880-1901), Series 1, Volume 19, Part I, p. 816. Cited hereafter as OR.

[3] Harsh, Flood, p. 166.

[4] Report of J.E.B. Stuart in OR, vol. 19, 1:816.

[5] Heros von Borcke, Memoirs of the Confederate War for Independence, Vol. I (London: Wm. Blackwood & Sons, 1866), p. 206.

[6] John Michael Priest, Before Antietam: The Battle for South Mountain (Shippensburg, PA: White Mane Publishing, 1992), p. 107.

[7] George G. Grattan, “Boonsboro Gap, or South Mountain,” in Southern Historical Society Papers, No. 1, Volume XXXIX, p. 34.

[8] Daniel H. Hill, “The Battle of South Mountain, or Boonsboro. Fighting for Time at Turner’s and Fox’s Gaps,” in Robert U. Johnson & Clarence C. Buel (eds.), Battles and Leaders of the Civil War, Volume 2 (New York, NY: The Century Company, 1887), p. 560.



2 thoughts on “Blog

  1. So, McPherson thinks Lee’s army, which he describes as “ragged, hungry, shoeless,” numbering but 33,000, would have marched fifty miles to Gettysburg? This fellow is a “military historian?” Please.

    • Joe –

      My point exactly. I was very surprised that McPherson would pose such a fanciful scenario. Hence my article on the realities facing Lee at the time. Thanks for visiting!

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