Was Lee’s “Lost Order” a Turning Point? (part three)

TurningPoints-logo(part three of three)

What exactly the Lost Order told McClellan has been the subject of much heated debate and controversy almost from the moment he glanced its contents.

From an intelligence standpoint, the Lost Order was important to McClellan, but not as much as has often been portrayed. As stated in the previous installment of this series, the most perplexing part about the campaign thus far to McClellan had been what Lee’s movements, heading in two different directions, meant. Now, the Lost Order simply solidified in McClellan’s mind exactly what Lee’s odd movements were all about. “I obtained reliable information of the movements and intentions of the enemy, which made it clear that it was necessary to force the passage of the South Mountain range and gain possession of Boonsborough and Rohrersville before any relief could be afforded to Harper’s Ferry.”[1]

Despite the clarification, the Lost Order was four days old when McClellan read it, and the wording called for the various parts of Lee’s plan to be achieved by Friday, September 12—the day before Union soldiers found the order. 

Naturally, the first thing to be done was to get his cavalry chief Pleasonton to verify the days old order. At 3:00 pm, Chief of Staff Randolph B. Marcy updated Pleasonton’s mission.[2] While time faded away as Pleasonton’s horsemen went about their business determining the veracity of the order, McClellan, now very aware of the possibility that Lee’s army may be divided in his front, pushed more of his army in that direction almost instantaneously.[3]

While setting the van of his army in motion, McClellan continued to browse through the order. It did seem that the discovery was a great find, but for as much as it told McClellan of Lee’s thus far undetermined intentions, the fog of war did not dissipate away like an early morning’s blanket of haze.

First, the order—which had been addressed to Gen. D.H. Hill, dropped by someone in the Confederate army, and then scooped up by three Indiana soldiers—began with Paragraph III. Either the Confederate high command proved unable to perform a simple arithmetic function (a highly unlikely proposition) or there was more to the order than what McClellan held in his hands. What did the first two paragraphs say further about Lee’s intentions?

A simple glance in the Official Records reveals that Paragraphs I and II state nothing about Confederate plans in Maryland. For McClellan to have known that was an utter impossibility. Certainly, the unanswerable question hung over his head throughout all of this: what was missing from the Lost Order?[4]

The wayward copy of Special Orders No. 191 also did McClellan no favors in the numbers department, already not one of the general’s best attributes. Earlier reports flooding into headquarters told McClellan of an enemy force numbering as high as 200,000 strong.[5] By the end of September 13, McClellan lowered this estimate not quite by half, concluding the enemy in his front “amounts to 120,000 men or more.”[6] The Lost Order does not mention anything of troop strength, but clearly designates five separate enemy columns before dropping in two vague references to the main body. Was the main body another column or one of the columns already mentioned, just by a different name? In addition, the very essence of Lee’s plan outlined in Special Orders No. 191 suggested a large number of Confederate soldiers in Maryland. Would the enemy divide itself into such disparate columns in a foreign land if it was such a small force? The Lost Order could not answer that question either.

Despite all of this, McClellan did plan an attack for September 14, armed with the solid information he did glean from Lee’s campaign plan. He began moving his forces into position on September 13 to carry the next series of ridges cutting north-south across the landscape of western Maryland.[7] So if the Lost Order did not provide McClellan with all of the information that he might have sought from such a fortuitous find, what then did it do?

As September 12 ended, the Army of the Potomac’s goals were to push west from Frederick and gain possession of Catoctin Mountain, a natural defensive barrier buttressed even more by the Confederate cavalry guarding the mountain passes. McClellan hoped that by carrying this mountain, Pleasonton’s cavalry could be in position the next day to go up and over the next barrier facing him—South Mountain.

The battle of South Mountain occurred on Sunday, September 14, and probably would have happened anyway, though perhaps on a smaller scale, as a natural extension of the Federals’ westward movement from Frederick whether the Lost Order was discovered or not. In McClellan’s first written report of the campaign, dated October 15, 1862, he also rightly recalled that the first place he received “reliable information that the enemy’s object was to move upon Harper’s Ferry and the Cumberland Valley, and not upon Baltimore, Washington, or Gettysburg” was while in Urbana on September 12.[8]

This is not to pronounce that the Lost Order had no significance whatsoever. Until that document came into McClellan’s hands, he was peering through the smoke screen attempting to derive the intentions of his opponent mostly unsuccessfully. Where the Lost Order proved crucial to McClellan’s intelligence reports was in its clear indication of what Confederate movements towards Harpers Ferry and the Maryland-Pennsylvania line meant. There were many other questions Special Orders No. 191 presented to the commanding Union general, but Lee’s intention no longer remained one of them.

The discovery of the Lost Order truly is an incredible story. Who could not indulge in a story like it? Its mysterious loss, the seemingly impossible find by three soldiers in a field, and its path up the chain of command right into George B. McClellan’s grasp accord the story a legendary status that few novelists could have framed better. Unfortunately, its import to the outcome of the campaign—and the war, say some—has been whisked into the legend of the Civil War.

Again, to say that the Lost Order’s odyssey is insignificant misses the point. To say that everything that subsequently happened in the Maryland Campaign hinged on this amazing story likewise does not stick to the track of the historical record. It is a story worthy of the ink spilled over its discovery, but does not accord it with the title of a major turning point of the Civil War.

[1] Report of George B. McClellan, OR, vol. 19, pt. 1, 26.

[2] Randolph B. Marcy to Alfred Pleasonton, September 13, 1862, 3:00 pm, OR, vol. 51, pt. 1, 829.

[3] Randolph B. Marcy to Jacob D. Cox, September 13, 1862, 3:35 pm, ibid., 827; Edward M. Neill to Orlando B. Willcox, September 13, 1862, ibid., 827-28.

[4] The full text of Special Orders No. 191 is found in OR, vol. 19, pt. 2, 603. The text of the Lost Order can be found in McClellan’s Report, OR, vol. 19, pt. 1, 42-43. The Lost Order reproduced in McClellan’s report omits the paragraph numbers, but the original copy of the Lost Order found in McClellan’s papers in the Library of Congress show the oddly numbered order, GBM Papers, LOC, reel 31.

[5] Andrew G. Curtin to George B. McClellan, September 10, 1862, 10:00 am, OR, vol. 19, pt. 2, 248.

[6] McClellan to Halleck, September 13, 1862, 11:00 pm, ibid., 281.

[7] In addition to the references previously cited in this work, George B. McClellan to William B. Franklin, September 13, 1862, 6:20 pm, OR, vol. 19, pt. 1, 45-46, also provides information about the Army of the Potomac moving into positions to strike at South Mountain and relieve Harpers Ferry on September 13.

[8] McClellan’s Report, ibid., 26-27.

14 Responses to Was Lee’s “Lost Order” a Turning Point? (part three)

  1. No, given the results, and the time that transpired, no it was not, as the author concludes at the end of this fine series. Here is one question I have: did anyone among the Union leadership think that the ‘discovery’ of Lee’s plans might be a ruse, for the express purpose of throwing them off? Is there any record of that possibility ever coming up?

    1. I haven’t seen anything confirming that. I have seen a couple of extremely convoluted theories that in fact it was a ruse – with reasoning akin to the idea still floating around after 54 years that Oswald did not act alone. I’ve always wondered why anybody – then or now – in his right mind would think it was deliberate deception. It was discovered in a field wrapped around cigars. The purpose of deliberate deception is to make sure that Union HQ actually got it. This may be the most idiotic method to achieve that result which one could imagine. It might not be found. It might be found by somebody who took the cigars and tossed the wrapper. It might be found a week later. The way you do it is to arrange for a courier to be “captured”.

      1. You say that this would be an ‘idiotic’ means to get such a deceptive document into the Union HQ, YET, that document was indeed found and brought to them. Let’s see here. Lee’s plans fall right into Mac’s hands out of the blue, and nobody would question it?. Where and how they were found would certainly be a logical basis for questioning their authenticity. Don’t get me wrong, this ‘means’ of conveying such a deception doesn’t seem likely, I get that. BUT, it’s a fair and logical question to ask if anyone among the Union commanders questioned them. If they didn’t, fine. As you say, you’ve seen no evidence of that. Neither have I. But I also don’t know everything about this incident.

      2. It’s not only not “likely” – the odds are astronomically against it. The fact that the unlikely happened doesn’t mean that it was cleverly-planned or, more to the point, that anyone planning this would arrange for a copy to be dropped in a field on a random date hoping that on another random date luck would intervene and get it to Mac. I haven’t even mentioned other things that could have happened – such as a deluge the night of September 12 which makes it unreadable. What do you think Lee’s reaction would be if you proposed this as the method to effect a “plant”?. If the ruse idea even popped into Williams’ or Pittman’s or McClellan;s head, they would have had to apply some common sense and/or put themselves in Lee’s head. They decided it was genuine. They were right. The only question was whether the orders were now out of date and had been changed. Again, I haven’t seen evidence that anyone questioned it as a ruse but if they did I’d be surprised if they spent much time cogitating about that.

      3. But you are presupposing quite a few things here. You choose words like ‘random’. If it was considered a ruse, by anyone, and thus opening the possibility that someone DID do this, what would be random about any aspect of it on the Confederates side? I think this method makes much more sense than having a courier ‘captured’. WWII turned to some degree on a supposedly ‘random’ finding of a body floating in the Med that just happened to have ‘detailed plans’ attached. That was a planned ruse that worked BECAUSE if the random nature of it. I don’t know why anyone would be so threatened by a question like this. To have such a MIRACULOUS occurrence happen would BEG that it be questioned to some degree, regardless of how small that degree was.

        Below is a link that offers up quite a bit about this incident and the resulting battles. I strongly recommend that it be read. It does NOT prove anything, but it DOES offer some relevant questions. Evidently there are others who dare to ask what I have and are not challenged by any perspectives offered…


      4. Douglas: I’m not “challenged” by the question – I’m simply rejecting as implausible the notion that it was deliberately planted as a ruse. (My reference to “idiotic” was not directed at your question but at the method of doing this – I should have been clear about that). We can go back and forth all day but if one assumes that the intent of a deliberate plant is to get it to McClellan, the method used makes no sense – as opposed, for example, to having a courier allow himself to be “captured”. The orders were issued on September 9. If an effective “ruse”, they would have to be received by McClellan in short order, to avoid the obvious problem which in fact occurred – McClellan’s concern that they were “stale”. Lee could have had no reason on the planet to suspect that three or four days later, a Union regiment would be halted in this field and that a member of that regiment would walk over, pick up the cigars, read the wrapping, and decide to send it up the ladder. Far too many of these and other rolls of the dice to make this a remotely reasonable way to effectuate a “plant”. As Kevin has suggested, the only concerns of which we are aware on the Union side were possible staleness and the authenticity of Chilton’s writing. I still think it’s useful; to imagine presenting this method to Lee as a way of deceiving McClellan and Lee’s response..

      5. John, the entire rational of pulling such a ruse would be to get the matter TO McClelland. REGARDLESS of the method decided on. It would stand to reason that the Confederates would have Union units under observation in order to ‘drop’ such a document in their vicinity. This is a logical question to ask, if a ruse might be in play. Per the link I offered, others have indeed been questioning the veracity and authenticity of it. It’s JUST a question. We KNOW that it was accepted as real, and all have confirmed them in the aftermath of the war. But I maintain that it would have been both reasonable and prudent to ask if it was real. The fact that the handwriting was confirmed as authentic (that of Chilton’s) at the time does seem to confirm that SOMEONE in the food chain there in Mac’s HQ deemed it necessary to inquire about it. Again, this is about actions and QUESTIONS at that particular time.

      6. Maybe we’re not in significant disagreement. My point is that I doubt anyone would expend much effort in exploring that (as opposed to asking the question initially) for the reasons I’ve given. Checking Chilton’s handwriting could be seen in part as tied to that question. I say “in part” because I think one would naturally ask “is this real” without moving on to further “ruse” analysis (which if it were suspected as a ruse should follow confirmation of the handwriting)- in other words, once it was deemed authentic, I’m not surprised that we have no record of anyone then pursuing the “ruse” angle. I am convinced that had this method been proposed to Lee he would have had his staff undergo a fitness evaluation,.

      7. By the way, Ryan’s theory is the one I alluded to originally. It all sounds great until we get to the “dropped in the field” part. With all due respect to Ryan, that’s an absurd method of maximizing the chances that this great deception get to McClellan. The fact that a few fortunate rolls of the dice took place doesn’t prove otherwise. As a young kid I actually saw the powerless Maury Wills hit 2 home runs in one game. That doesn’t mean that he should have been penciled in as the clean up hitter. This is entirely aside from the fact that McClellan’s response (albeit not as efficient or expeditious as it should have been) resulted in a near disaster for Lee at the passes. Some ruse….

      8. Bruce Catton actually asked the same question – nobody seems to have remembered lighting them up.

    2. Hi Douglas, thanks for your question. It is a good one. There does not seem to be any indication that anyone among the Federal high command believed the discovery of 191 was a ruse. Even James Longstreet, after the war, wrote, “Ordinarily, upon getting possession of such an order, the adversary would take it as a ruse de guerre, but it seems that General McClellan gave it his confidence…”

      If there was any notion amongst the Federals that it was a ruse, that was dispelled by the time it came into McClellan’s hands, thanks in large part to 12th Corps staffer Samuel Pittman. Pittman knew Robert Chilton, the scribe of the Lost Order, before the war and knew his handwriting. Thus, he was able to verify the order’s authenticity that way before McClellan saw it.

      As for whether or not Lee planted the document for the Federals to find it, there are those who subscribe to that belief. Personally, I think it’s too much wishful thinking on Lee’s part that a document laying in a field under a tree would be found by the Federals, recognized for what it was, and then make its way into McClellan’s hands. However, the joy, if you will, of the saga of the Lost Order is that we will never know for sure how it was lost and who lost it, so we don’t know exactly for sure. My belief is that the document was dropped by mistake, not as a ruse, but everyone has their opinions, which makes history fun!

      1. Kevin, thank you for your reply here. This has been a great series, and I have enjoyed reading it and taking part here in the aftermath. I echo that I have never found anything to indicate it was treated as anything other than real, but it just seems to me to be a common sense question to ask at the time. This ‘miracle’ from ‘out of the blue’ falling right into their laps. Who would have thought? LOL. The only other thing I will offer here along the lines perpetuating the possibility of a ruse is the reference you made about Chilton actually writing it. It would make eminent sense to have someone like him to be involved for that express purpose (of a ruse) knowing that there would be those on the other side who could confirm his handwriting. But again, this has been great.

  2. This is good analysis, which takes the proper “step back” and asks what difference the discovery actually made.Of course, as is always the case with McClellan, nothing’s ever easy. His notorious “12 M” telegram to Washington (and i’m not looking to go down that rabbit hole) is pretty effusive about what he;d gotten his hands on – which itself is inconsistent with his less-than-hard prodding of Franklin despite McClellan’s own previously-expressed criticism of Franklin. And then. as you suggest, there is the ever-present issue of Mac’s defective calculator when it comes to enemy strengths.

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