Battle of Gettysburg, General Robert E. Lee and Sun Tzu

The American Civil War is Sun Tzu’s nightmare scenario. A bloody stalemate that will end up costing 620,000 lives. It is by far the deadliest war in American history.

Union Soldiers

By 1863, it was very clear that this was not going to be the short war that everybody thought that it was going to be.

In the Battle of Bull Run at Manassas, the ladies and gentlemen drove out of D.C. in their carriages with picnic lunches to observe what they thought was going to be the first and last battle of the Civil War. Everybody knows by now in 1863 that it’s going to be a long war.

The war affects every American, sometimes in unexpected ways.

The Civil War sees the creation of the first American Psychiatric Hospital at Saint Elizabeths in Washington D.C., still in operation today.

Saint Elizabeth Psychiatric Hospital Washington D.C.

The war between the North and South also affected how the Americans received their mail. A Cleveland Postmaster becomes so distraught by the sight of anxious wives and children lining up at his Post Office, that he institutes “Home Delivery” for the very first time. Although what many homes receive, are Death Notices.

The Turkey Buzzards realized that whenever they saw an Army, that sooner or later, there would flesh to eat. When the Armies moved along, they moved along with hundreds of Turkey Buzzards flying overhead, just waiting for the battlefield, waiting for the carnage, waiting for the open wounds, to peck out their eyes and eat the innards as they would any other carrion. It’s a horrific scene but that’s what war is, pretty horrific.

Civil War field hospitals are human butcher shops with arms and legs stacked in piles. Some 40,000 amputations are done on the Union side alone and only 24,000 of them under anesthesia. Doctors performed dozens of surgeries without ever washing their hands. It was considered 7 times safer to fight through the entire Battle of Gettysburg than it was to be sent to an Army Hospital. The death rate in the Army hospital was 30-40%. Taking the limb off was one part of it, but another part was dealing with gangrene and infection and the death rates were just staggeringly high.

Field Hospital

The American Civil War is a classic example of why Sun Tzu warns against going to war in the first place. But other principles of war will prove instrumental in how the war eventually ends.


Those skilled in war bring the enemy to the field of battle. They are not brought by him. – Sun Tzu


Pennsylvania 1863. The Civil War is a bloody stalemate.

By the end of June of that year, Confederate General Robert E. Lee moves his Army of nearly 60,000 men into Union territory. While most of the battles of the American Civil War has been fought in the South, Lee decides that the moment is right to invade Union soil. Lee’s plan – destroy as many military posts as possible in Maryland and Pennsylvania while the Union Armies defend Washington D.C. One key target is Camp Curtin just outside of Harrisburg, Pennsylvania, which happens to be the largest Military Supply Depot in the North.

The strategy of Lee’s attack on the North is not primarily military, it’s political. He’s going to essentially try to defeat Lincoln politically. What he hopes is a massive defeat of the North will encourage people to lose faith in the war.

Lee’s bold military action to achieve a political victory is more a Chinese Go strategy than a Chess strategy. Exactly the kind of plan that Sun Tzu would have admired.

But as Lee’s main force moves North, a skirmish erupts in Gettysburg between two Calvary units.

Confederate General Henry Heth had a division at Cashtown and he wanted to move over to Gettysburg in order to get some shoes from a factory there. That was the only reason he went. In this fashion, he moved without any understanding about what lay ahead of him and in the process set off the greatest battle that has been fought in the western hemisphere.

General Lee gets word of the skirmish and is told that a major Union force is at Gettysburg. Instead of sending a Calvary reconnaissance force to confirm the report; Lee orders his entire Army to mobilize. It’s a colossal mistake.

General Lee decides to abandon the original plan. He gives up what’s called “Strategic Aim” and he makes the mistake of allowing operational development to drive strategy.

General Lee then orders all his forces to converge at Cashtown, Pennsylvania, a small village 7 miles from Gettysburg.

Sun Tzu would not like his choice as Cashtown has not been fully scouted.

If General Lee had read Sun Tzu, he would have known better than to proceed with what you “think” is happening and try to spend the resources to find out what really is happening.


Move only when you see an advantage and there is something to gain. Only fight if a position is critical – Sun Tzu


Some 60,000 Confederate Troops pour in from nearby Cashtown and Carlisle.

3,000 Union soldiers take the position on McPherson Ridge. They try to hold off the onslaught of enemy soldiers until help arrives. But reinforcements are miles away toward Washington D.C.

McPherson Ridge

So the Union soldiers withdraw Southeast onto Cemetary Ridge. A range of hills that form the shape of a fish hook.

Cemetary Ridge provides an extremely strong defensive advantage. The terrain is so obvious in favor of the defense that any 2nd Lieutenant from Westpoint would have chosen that position given the opportunity to do it.

When Union General Winfield Scott Hancock arrives, he declares it the best natural defensive position that he’s ever seen. He immediately sees the danger of the Union’s position, but because the Union troops are still staggering in, he believes that they are vulnerable.

Cemetery Ridge

General Lee then gives an order to Confederate General Richard Ewell that many believe wasn’t even an order at all.

General Lee says to him – “Attack when you think it’s practical.” He didn’t order him to attack. General Ewell, who was new to the battlefield and didn’t know what was going on and decides not to attack. General Ewell decided that it was not practical because his troops were tired, exhausted and he wanted them to get some rest.

ConfederateGeneral Richard Ewell

While some criticize General Ewell for not following orders, Sun Tzu’s only words place the blame on General Lee.


If instructions are not clear and commands not explicit, it is the fault of the General. But if the orders are clear then it is the fault of the subordinate officers that the orders are not obeyed. – Sun Tzu

Sun Tzu famously demonstrated this to King Helu by using the palace Concubines.


At Gettysburg, we see General Lee issuing very unclear and very ambiguous orders to his subordinates.

Confederate General Robert E. Lee

Union reinforcements soon arrive and strengthen their positions and General Lee now faces an uphill battle against a strong enemy position.


When the enemy occupies high ground, do not confront him. If he attacks downhill, do not oppose him. – Sun Tzu


As night falls on the first day of the Battle of Gettysburg, Lee confers with Confederate General James Longstreet. A man who grasps the situation from Sun Tzu’s perspective.

General Longstreet wants Lee to abandon the idea of attacking the Union high ground. Instead, he wants to march south, around Cemetary Ridge and then east right toward Washington D.C. This will force the Union Army to come off of Cemetary Ridge and attack the Confederates where they are and if they attack, then they feel that they would win. This maneuver would have been precisely what Sun Tzu would have recommended.

Confederate General James Longstreet

General Lee says “No” to the idea. He then points to Cemetary Ridge and says – “The enemy is there and I am going to attack him there.” Lee has completely given up his Go strategy and reverts back to Chess.

General Longstreet is stunned. He sees the Union Army dug in on the hills and knows that they should not be attacked.

Sun Tzu would have advised against it. He would have said – “Access the situation. Adjust your forces. Find another way to attack the enemy.”

But General Lee doesn’t listen and the second day of Gettysburg is hell on earth.

The pastures are transformed into fields of slaughter in places like Plum Run and the Peach Orchard and Little Roundtop saw some of the bloodiest hand to hand combat of the war.

What’s terrible about hand-to-hand combat is the memories. For a lot of war, you can pull the trigger and maybe see somebody drop… maybe. Most often, you don’t. Hand-to-hand combat is up close and personal while you’re fighting with bayonets, knives, rifle butts and Pistol shots in the head and the face. You see it viscerally and it takes a “piece” out of you which is why you have psychiatric casualties. God knows how many soldiers, from both sides, remember that battle every night for the rest of their lives. It was just gory beyond belief.

Hand to Hand Combat

On top of Little Roundtop, Union Colonel Joshua Chamberlin with the 20th Maine Regiment. They had survived three Confederate charges and are nearly out of ammunition.

Here come the fourth attack and Chamberlin orders “Fix Bayonets!”.  Everybody fires their last 2 rounds and they stand up and the great moment in history when Colonel Chamberlin stands on the wall with his saber which rings through the years of American Infantry history when he yells – “Follow me, boys! Bayonets Forward!” And down they went in a bayonet charge.

Colonel Chamberlin leading bayonet charge

The Union troops howl down the hill.

Shocked at the charge, the Confederate soldiers retreat. Against all odds, the Union hangs on to Little Roundtop. Colonel Chamberlin was eventually to get the Congressional Medal of Honor for this heroic action.

Sun Tzu’s principle of never attacking an enemy on the high ground held true.

But this does not seem to deter General Lee who wants to attack yet again and order his men to attack uphill one more time.


There are some Armies that should not be fought. Some ground that should not be contested. – Sun Tzu


When the sun rises on the third day on the Battle of Gettysburg, despite the thousands of dead bodies strewn across the battlefield, Confederate General Robert E. Lee is about to order his troops to attack the high ground yet again.

One of the things you never want to do in war. Never throw good money after bad. Follow the advice of Sun Tzu.


Use an attack to exploit a victory. Never use an attack to rescue a defeat. – Sun Tzu


General Longstreet “gets it”. He tries once again to convince General Lee to move around Cemetary Ridge and threaten Washington D.C. to draw the Union off the high ground.

General Longstreet understands that the Confederates are in a terrible position. They’re outnumbered, they do not have the high ground and they have suffered terrible casualties in the last 2 days of fighting. And that there is no real chance of pushing the Union Army off the high ground.

But General Lee feels that his men have sacrificed too much to turn back now. He gives the order to attack.

The Infantry charge is led by Major General George Pickett.

George Pickett

The story goes that General Longstreet is sitting there and Pickett asks him – “Shall I go General? Shall I go?” and Longstreet just drops his head and looks away. Pickett asks once again – “General, shall I go?” and Longstreet looks away and he says “General, I’m going into the attack.” and Longstreet looked away again. Longstreet never gave the order to attack because he knew it would be suicidal.

In the sweltering July heat, 12,500 Confederate soldiers led by Pickett make their determined march across an open field nearly a mile long.

As they advance in close ranks, thousands are cut down by Union artillery and rifle fire.

Pickett’s charge

There was nowhere that they could hide. There was almost no range between the Union forces and the Confederate forces and the Union forces were simply able to stand behind their reinforced positions and fire on the Confederates and so the Confederates had no way of defending themselves.

To Pickett’s men’s bravery, they continued all the way out. There was one whole unit from South Carolina that marched straight into the Rhode Island artillery gun and they were completely destroyed by canister shot. They all died instantaneously. It just tore through people, limbs were blown apart, heads, eyes, and blood everywhere.

Of the more than 12,000 Confederate soldiers who made the charge, only 5,000 survived. The battle of Gettysburg is over.

Sun Tzu would have been horrified at the tragic waste of Pickett’s charge. Sun Tzu always believed in using the intellect rather than force and never attacking headlong into an enemy force if you can do otherwise.

At Gettysburg, General Lee doesn’t adjust his strategy to the situations on the ground. He refuses to retreat even when the situation is clearly hopeless.

General Lee famously takes off his hat and walks into the field and says – “It’s all my fault boys. It’s all my fault.”

You’re damned right General. It’s all your fault. Nobody in his right mind would have ordered that. He should have listened to Sun Tzu.

In the end, it’s General Lee’s failure to follow Sun Tzu’s wisdom is what costs the Confederates the war.

















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