When Civil War students rate the top generals of the war, Robert E. Lee and George B. McClellan can usually be found at opposite ends of the rankings. Though he has had some detractors, Lee is commonly found among the war’s best and, though he has had some proponents, McClellan’s name can usually be located towards the bottom of these fantasy lists. These exercises can generate excellent discussion of the merits of certain generals over others and what makes a good leader in wartime.
Today, we can find these debates at roundtables, blogs, websites, and more. Civil War soldiers talked among themselves about these same things, then around a campfire. While their fantasy hierarchies rarely exist from 160 years ago, pieces of them can be surmised. Indeed, a part of Robert E. Lee’s list exists in numerous accounts of the general’s conversations. Surprisingly, you could expect to find McClellan near the top of Lee’s ratings. (Pause here and let that sink in for a second.)
The most common version of Lee ranking McClellan among the war’s best—if not the best—is recorded in Robert E. Lee Jr.’s Recollections and Letters of General Robert E. Lee, published in 1904. After the war ended, a son of one of Lee’s cousins asked the former general “which of the Federal generals he considered the greatest,” to which Lee “answered most emphatically ‘McClellan by all odds.’”
Lee’s statement might not be the only thing raising your eyebrows. His assertion was recorded only in 1904, 34 years after his death, and not by the person who Lee was talking to. However, let’s not discard this story just yet. (Either way, I don’t always think we should trash a story because it was not recorded contemporarily.) A wartime letter written by a friend of McClellan’s to the general reported that his own friend had just returned from the Confederacy. While there, he supposedly heard one of Lee’s daughters exclaim, “Genl McClellan was the only Genl Father dreaded.” Furthermore, on January 18, 1869, Lee said of his former Union adversary, “As regards General McClellan, I have always entertained a high opinion of his capacity, and have no reason to think that he omitted to do any thing that was in his power.” Clearly, Lee praised McClellan enough for there to be substance to his assessment, and not to simply brush off Lee’s statements as tongue-in-cheek jesting or as a creation of someone’s imagination after Lee’s death. All of this begs the question then: what should be made of Lee’s respect for McClellan’s capabilities, and why did he feel that way?
After sorting through all of the times Lee talked about McClellan as a general, it appears Lee respected him in a two-fold manner. First, Lee’s respect for McClellan was rooted in the Federal general’s soft-hand approach to the war and to the Confederacy. In November 1862, upon receiving word of McClellan’s removal from command of the Army of the Potomac, Lee told Lt. Gen. James Longstreet that he regretted the change because “we always understood each other so well. I fear,” Lee continued “they may continue to make these changes till they find some one who I don’t understand.” In his memoirs, Longstreet expanded upon Lee’s feelings:
When informed of the change, General Lee expressed regret, as he thought that McClellan could be relied upon to conform to the strictest rules of science in the conduct of war. He had been McClellan’s preceptor, they had served together in the engineer corps, and our chief thought that he thoroughly understood the displaced commander. The change was a good lift for the South, however; McClellan was growing, was likely to exhibit far greater powers than he had yet shown, and could not have given us opportunity to recover the morale lost at Sharpsburg, as did Burnside and Hooker.
Historian Ethan Rafuse wrote, “McClellan and Lee shared a common understanding of the strategic, organizational and operational dynamics of the Eastern Theater and the war in general. It was this shared understanding, rather than the disparagement of his foe’s considerable abilities that was at the heart of Lee’s remarks.”
Plenty of episodes during the Peninsula Campaign confirm McClellan’s and Lee’s shared understanding. During that campaign, the property of Lee’s son Rooney—White House—fell into Union hands. Lee’s wife Mary and two of their daughters were there and eventually they became trapped behind Union lines. McClellan assured Lee his property would be protected and even arranged safe escort for Lee’s family to Richmond. No doubt Lee was relieved.
Throughout the campaign, as the armies inched closer to Richmond, McClellan and Lee kept up a regular correspondence regarding the exchange of prisoners of war. The two generals established representatives from their respective commands to handle the matter and agreed that medical personnel left behind to tend wounded soldiers were not to be handled as combatants in such exchanges. Between June 18 and 21, 1862, both men even diffused a potentially nasty situation regarding the execution of prisoners and subsequent retaliatory measures that were prepared but never carried out. When it came to how the war should be conducted between two opposing forces, the two clearly understood each other well.
Lee’s respect for McClellan went beyond these off-the-battlefield matters, though. After the war, Lee pegged McClellan “an able but timid commander,” and the military record between the two justifies why Lee thought McClellan a capable battlefield commander. At the outset of the Peninsula Campaign at the Siege of Yorktown, Lee served in Richmond at President Jefferson Davis’s side. The reports he received from Maj. Gen. Joseph Johnston on the front lines were not favorable. As the siege lines grew longer, Johnston wrote Lee, “We are engaged in a species of warfare at which we can never win. It is plain that General McClellan will adhere to the system adopted by him last summer, and depend for success upon artillery and engineering. We can compete with him in neither.” In a no-win situation, Johnston pulled his army back closer to Richmond while searching for an opportunity to strike McClellan where he could not utilize his superior numbers, artillery, and engineering. Johnston launched that attack on May 31, 1862. The Battle of Seven Pines (Fair Oaks) did not produce the results Lee and Johnston hoped for. Johnston also fell wounded and Davis appointed Lee to command his army.
Four days after taking command, Lee predicted his enemy’s next step. “McClellan will make this a battle of posts,” he began. “He will take position from position, under cover of his heavy guns, & we cannot get at him without storming his works, which with our new troops is extremely hazardous. You witnessed the experiment Saturday [Johnston’s May 31st attack]. It will require 100,000 men to resist the regular siege of Richmond, which perhaps would only prolong not save it. I am preparing a line that I can hold with part of our forces in front, while with the rest I will endeavour to make a diversion to bring McClellan out.” Lee worked hard “to bring McClellan out” and fight him on a fair field of battle. He did in late June and drove McClellan away from Richmond, though the results were not quite as Lee hoped. His attacks hurt McClellan’s army but did not destroy it. The ground his army won back from the Federals was won at a heavy casualty count.
In September 1862, at the beginning of the Maryland Campaign, Lee voiced his opinion of McClellan’s generalship. “He is an able general but a very cautious one.” Following the Confederate victory at Second Manassas, the Union forces under McClellan’s command were “in a very demoralized condition, and will not be prepared for offensive operations—or he will not think it so—for three or four weeks.” In reality, McClellan was already moving in the direction of Lee’s army. During the campaign, Lee said McClellan’s advance was “more [rapid] than convenient” for him. After the campaign, Lee expressed being filled “with amazement” at the rapidity with which McClellan rallied Federal troops after Second Manassas and marched out of Washington, DC, to meet Lee in battle. Ultimately, McClellan shattered Lee’s timetable of events and prevented Confederate victory in Maryland. Even days before McClellan’s removal from command, Lee was surprised by the way McClellan moved his army. After McClellan’s removal, Lee had a new adversary to learn.
Unfortunately, Robert E. Lee never expanded upon his statements about McClellan’s generalship; we are only left to wonder what he really meant. However, there is enough documentation to provide context to Lee’s assessment. At the end of the Civil War, McClellan did not rate highest among Union military commanders. To Lee though, he was an able opponent. The Confederate chieftain respected McClellan’s code of conduct during the conflict and McClellan’s ability to use his advantages as a commander and those of his army to make the Confederacy’s war aims difficult to achieve. McClellan showed Lee the limits of the Confederacy’s capacity to wage war. Throughout the rest of the war, Lee kept those lessons he learned in mind and sought to avoid the “battle of posts” in favor of decisive, offensive battlefield victories. Each general understood what they each needed to do to accomplish their objectives, and they each understood that doing so against one another would be no easy task.
 Robert E. Lee, Recollections and Letters of General Robert E. Lee (New York: Doubleday, Page, & Company, 1904), 416.
 Quoted in letter to McClellan from “A Friend,” March 28, 1863, Reel 35, George B. McClellan Papers, Library of Congress.
 J. William Jones, Personal Reminiscences, Anecdotes, and Letters of Gen. Robert E. Lee (New York: D. Appleton and Company, 1875), 238-39.
 James Longstreet, “The Battle of Fredericksburg,” in Battles and Leaders of the Civil War, vol. 3 (New York: The Century Co., 1888), 70.
 James Longstreet, From Manassas to Appomattox (Philadelphia, PA: J.B. Lippincott Company, 1896), 291.
 Ethan Rafuse, “Robert E. Lee and George B. McClellan Battled to win the War in the East,” The Courier 14, no. 5 (2010): 2.
 E.C. Gordon to William Allan, November 18, 1886, in Douglas Southall Freeman, Lee’s Lieutenants: A Study in Command, vol. 2 (New York: Charles Scribner’s Sons, 1943), 716-17.
 OR, vol. 11, pt. 3, 477.
 Robert E. Lee to Jefferson Davis, June 5, 1862, in Clifford Downey and Louis H. Manarin, eds., The Wartime Papers of R.E. Lee (New York: Bramhall House, 1961), 184.
 John G. Walker, “Jackson’s Capture of Harper’s Ferry,” in Battles and Leaders of the Civil War, vol. 2 (New York: The Century Co., 1887), 606. It should be noted that Walker’s account suffers from factual flaws, see Joseph L. Harsh, Taken at the Flood: Robert E. Lee & Confederate Strategy in the Maryland Campaign of 1862 (Kent, OH: The Kent State University Press, 1999), 143-45.
 Robert E. Lee to Jefferson Davis, September 16, 1862, in Dowdey and Manarin, eds., Wartime Papers, 309.
 Garnet Joseph Wolseley, “A Month’s Visit to the Confederate Headquarters,” Blackwood’s Edinburgh Magazine, January 1863, 18.
 OR, vol. 19, pt. 2, 698.