Which individual from the Civil War would be the most interesting to sit down and speak with over dinner or a tasty beverage? Robert E. Lee
By Jake Collens
The Cleveland Civil War Roundtable
Copyright © 2025, All Rights Reserved
Editor’s note: The subject of the annual Dick Crews Memorial Debate at the January 2025 Roundtable meeting was: “Which individual from the Civil War would be the most interesting to sit down and speak with over dinner or a tasty beverage?” Five members made presentations on the topic; the article below was one of those five presentations.
General Lee, as you know, I am from the Cleveland Plain Dealer. I want to thank you for sitting down with me today to discuss some of your thoughts and feelings about the “late unpleasantness.” I know you have been reticent to go public in the past, and I appreciate this opportunity. I want this to be an agreeable conversation, so I have brought along buttermilk to help make things pleasant.

The entire country is anxious to hear from you. I think, General, that you will readily admit that you belong on the Mount Rushmore of Civil War individuals. Your counterpart, General Grant, has published his memoirs, as have some other Union generals like Sherman and Sheridan. It’s important that we hear from the premier Confederate general. So, we begin.
General Lee, you stated in 1861 that “I do not believe in secession as a constitutional right, nor that there is a sufficient cause for revolution.” Late in the war, you told your son Custis, “When this war began, I was opposed to it, bitterly opposed to it, and I told these people that, unless every man should be able to do his whole duty, they would repent it, and now, they will repent it.” You have previously stated your life philosophy, namely, “the great duty of life” was “the promotion of happiness and welfare of our fellow men.” In light of these statements, I ask you, General Lee, do you think you did right in resigning from the U.S. Army and joining the Confederacy?

Secondly, you wrote your wife Mary in 1856, and I quote, “In this enlightened age, there are few, I believe, but what will acknowledge that slavery as an institution is a moral and political evil in any Country…I think it however a greater evil to the white man than to the black race, and while my feelings are strongly enlisted in behalf of the latter, my sympathies are more strong for the former.” Given that these were your true feelings, how do you justify fighting a war that many felt was primarily fought to defend slavery?
My next question also pertains to slavery. On January 12, 1865, responding to a letter from legislator Andrew Hunter requesting your opinion, you stated, “I think therefore we must decide whether slavery shall be extinguished by our enemies, and the slaves used against us, or use them ourselves at the risk of the effects which may be produced upon our social institutions. My own opinion is that we should use them without delay.” Further, you advocated “giving immediate freedom to all who enlist.” General Lee, in the last days of the Confederacy, slaves were, in fact, starting to be armed. Should this policy have been pursued much earlier?
General Lee, my fourth question concerns overall war strategy. Your president, Jeff Davis, believed the best path to victory was to follow the Revolutionary War defensive strategy and wear out and outlast the enemy. For the most part, you pursued an aggressive attack strategy, wherein you attempted to win the war by military victory. You won many victories in individual battles, but lost the war. In one of your greatest victories, Chancellorsville, you actually suffered a higher percentage of casualties in your army than did the Union army. The Union enjoyed a decided manpower advantage over the Confederacy. In light of these facts, would you, in hindsight, have modified your strategy?
On a similar matter, in most cases during the war, you resisted the allocation of manpower and resources to the Western Theater in favor of the East. Do you think this was a mistake and that a Western emphasis would have been more likely to be successful?
My next question is about your decisions regarding some aggressive attacks. General Grant was accused by his detractors of being a “butcher!” Grant has stated that he regretted only one attack – Cold Harbor. Do you regret any of your failed attacks? I specifically mention three: Malvern Hill in 1862, Pickett’s Charge in 1863, and last, the Battle of Fort Stedman on March 25, 1865.
My final question is this. You suffered a serious health issue at the Battle of Fredericksburg. You have stated that you never entirely recovered from it. Do you think your health affected your generalship at the Battle of Gettysburg or at any other time?
There are many other questions that need answered, yet this is a good start. Think carefully, General Lee. I await your thoughtful response.
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