How to Lead in a Losing Cause – Lessons from the Real Robert E. Lee


He lost the Civil War but is respected to this day, could control his emotions like nobody else, and kept a pet chicken for companionship.

Robert Edward Lee, the commander of the Confederate army in the U.S. Civil War is said to have never fired a single shot, but was responsible for the deaths of hundreds of thousands of people.

This elusive and misunderstood figure of history, despite being flawed, displayed both humility and a deep appreciation for the unexpected benefits of losing.

Today, these qualities possessed by Lee have much to teach us about leading ourselves, and others, in a world turned upside down.

“We must expect reverses, even defeats. They are sent to teach us wisdom and prudence.”

Lee won the vast majority of his battles, losing ground towards the end of the war. But he understood that with loss comes learning, greater determination, and the ability to prevent or minimize future loss. As a team leader or manager, see setbacks for what they really are – learning opportunities.

“We failed, but in the good providence of God, apparent failure often proves a blessing.”

Lee came to know that his defeat was in the best interest of a united America. Losing doesn’t need to be a bad thing. It can result in unforeseen outcomes that bring greater opportunity. Over time, today’s loss may be seen as tomorrow’s blessing.

“I tremble for my country when I hear of confidence expressed in me. I know too well my weakness.”

Despite being one of the greatest military strategists of all time, Lee kept his perspective. He knew his faults and planned accordingly. Historians speculate that had Lee believed in his own legend, he would have been far less cautious, leading to far greater losses. Lead and plan with weaknesses in mind. Show your team that you are human.

Recently in the news, in response to the destruction of a Robert E. Lee statue, commentators have accused Lee of being a champion for slavery – a disgusting human being who wanted to break up the United States.

Nothing could be farther from the truth. (Lee was dead against having monuments of himself, saying they “keep open the sores of war”). It is not well known, but a detailed look at history shows that the last thing Lee wanted to do was fight against the Union.

As the Civil War broke out – and southern states voted to separate and create their own country – Lee, by then a highly respected military leader in the United States Army, was asked by President Lincoln to be commander of the Union forces. Lincoln admired Lee and knew that he was a brilliant strategist on the battlefield – just the person Lincoln needed to win the war.

But there was one problem. And it tortured Lee. He lived in Virginia, a state that had joined the southern Confederacy. Lee didn’t really believe in the cause of slavery, but if he were to lead the Union army, he would have ended up fighting his own family and his own state.

To Lee – that was unacceptable. He decided to fight for Virginia. It was a decision that would cost the lives of almost a million people and drag the war over a gruelling 4 year period (1861-1865). It’s generally accepted that had Lee fought on the Union side, the war would have been short lived, due to his incredible skills combined with the large number of soldiers and resources of the North.

Lee knew that by deciding to fight for the South, his reputation would be stained, but it was a risk he was prepared to take, in defense of his homeland.

It’s believed that deep down, Lee knew his side would lose. He was outnumbered, out-gunned and out-financed. He was also up against a brutal General who was as smart as he was – Ulysses S. Grant (who later became president).

Much has been said about Lee’s bravery and tactics. For most of the war, he was able to win battles against the larger and more powerful battalions of the North, by surrounding them and taking them by surprise.

But historian and author Jonathan Horn says while it’s true Lee was brilliant, he didn’t view himself that way. Instead, Lee saw no other choice. He had to either use strategies to deceive “those people in the North” (as he called them, never referring to his fellow Americans as the enemy) or risk getting quickly annihilated.


In 1862, Lee acquired a horse named “Traveller” that not only survived the war, but outlived Lee. Traveller was with Lee in the “Second Battle of the Bull Run” becoming frightened and pulling Lee down a stump, breaking both of his hands. Lee spent the rest of that part of the war in an ambulance. The horse was still owned by Lee after the war and was part of Lee’s funeral procession.  

Some of the success of Robert E Lee, and a contributor to his downfall, was his ability to hold back emotion. As a cadet at West Point, he was reserved and dignified, seldom showing any emotion at all. Fellow cadets nicknamed him “the marble model.” Lee’s blank face would remain through his life, and when he surrendered to end the war, Union commander Ulysses S. Grant would comment “Whatever his feelings, they were entirely concealed.”

Much of the time, Lee’s tough exterior was an advantage – earning him respect and allowing him to lead his troops calmly, without outbursts.

But Lee’s bottled up frustrations and anger would be released through his actions – often with disastrous results.

On July 3, 1863, Lee invaded the North, ordering 15,000 troops to charge right in the middle of the Union army in the town of Gettysburg, Pennsylvania. He had under-estimated new weaponry used by the North, causing massive casualties and forcing him to retreat. (It was the first major defeat for Lee and showed the Union that he was not invincible). Why did Lee make such a bold, risky move? Many believe he acted too hastily simply because he was getting frustrated.


This remarkably well preserved photo shows an “ambulance wagon” and attendants in training for the Union army during the U.S. Civil War. During the war, different models were produced. The original 2-wheel wagon was only good for smooth roads, so later, this 4-wheel version was used to tackle rougher terrain.

While Lee seemed to be like a machine, incapable of love – his affections were on stage, not towards any other human being, but, of all things – a pet chicken.

Lee acquired a small black hen in 1862 from a shipment of chickens sent to his army for food. Originally, it is said that he kept the hen to eat its eggs, but over time, Lee grew fond of the bird, which he named “Nellie.”

The hen would stay by Lee’s side for over a year. But in July, 1863, following Lee’s defeat at Gettysburg, he noticed his beloved chicken was missing. A panicked Lee stopped the retreat of his army and ordered some of his soldiers to find her. The great General Lee, admired by millions for his tough exterior, was reduced to a panicked mess over the loss of a chicken.

The bird was found, and the relieved Lee then enabled his army to keep moving. Nellie’s demise came when Lee’s chef (a former slave) cooked the bird at a time when no other food was available. Lee was not happy.

Those who knew him, said Lee put importance on his pet hen because it made him think about his plantation back home and his family, allowing him to get through the difficult days and nights of the war.


When Robert E. Lee (on the right in the painting) surrendered in a farmhouse to Union commander Ulysses S. Grant, he was in full military attire, complete with traditional sash and sword – the picture of dignity and respect. (Grant arrived in a muddy field uniform). Just before the surrender, one of Lee’s officers suggested to Lee that he keep the war going and allow his soldiers to fight a guerrilla campaign (in which small, roaming groups of soldiers would use ambushes and raids to keep the fight going). Lee said no, replying: “If I took your advice, the men would be without rations and under no control of officers, they would be compelled to rob and steal in order to live.”

Lee met his wife Mary when they were both children. Over time, the friendship turned to romance and they were married in the summer of 1830. (Both were in their early 20s).

The Lees had 7 children, 6 of whom were born in the dressing room of their home, Arlington House. (All survived Lee except one).

Lee was critical of his wife’s housekeeping, but by all accounts, it was a loving and supportive relationship. (Although Lee did like to flirt with young women, there is no evidence of an affair).

When war broke out, Lee begged his wife to leave their home, fearing that Union soldiers would come and occupy their home. She left reluctantly (and Lee was right, the Union side did invade and take over their home, setting up cabins and using the hillside to fire artillery).

Mary developed severe arthritis and ended up in a wheelchair. She and her daughters spent the war years knitting hundreds of socks for Lee’s soldiers.

She loved her Arlington home so much, she wanted to go back to it after the war. She visited what was left of the property, recognizing only a few trees – then died a few months later.


This image shows the Virginia home of Robert E. Lee, known as “Arlington House” in 1861. At the end of the war, the 1,100 acre site was turned into the “Arlington National Cemetery”. The property had been purchased in 1802 by George Washington Parke Custis, the grandson of Martha Washington (wife of George Washington). The estate was passed to his daughter Mary, who became Robert E. Lee’s wife. When Mary was forced to leave the home due to the war, she buried many of her personal belongings throughout the property.

The first person buried at Arlington never saw a day of combat. Private William Christman died of disease like many other soldiers buried there.

Lee’s views on slavery are filled with contradiction. The story was told by the New York daily newspaper in 1859, citing two anonymous letters, that Lee personally had whipped a female slave named Mary Norris who had escaped and been recaptured along with her brother and cousin.

Even to this day, historians still argue whether Lee actually did it or not.

Mary’s brother Wesley, in an 1866 newspaper interview, said Lee told the escapees that “he would teach us a lesson we would not soon forget.” But Wesley did not say his sister was whipped personally by Lee – implying that it was others Lee had paid, who dished out the brutal punishment.

As recently as 2014, Civil War author Michael Korda, after reviewing all of the historical records, said it was not part of Lee’s character to do such a thing. But Korda has added, “He may not have flinched from observing it to make sure his orders were carried out exactly.” (Lee himself had denied the whipping).

A few years prior to the reported incident, Lee wrote a letter in which he called slavery a “moral and political evil”, adding that slaves must be treated kindly. However, he went on to say “The painful discipline they are undergoing is necessary for their instruction.”

One slave who had been owned by Lee was quoted as saying he was “the worst man I ever see.”

After Lee surrendered and the war was over, he was not arrested or punished. He did lose his U.S. citizenship and made an application to have it restored, but the application was not honored.

Amazingly, over 100 years later in 1970, the same application (in the form of an amnesty oath) was found by an archivist at the National Archives. In 1975, Lee’s rights of citizenship were retroactively restored effective June, 1865.

After the war, Lee was exhausted and desperate to lead a quiet life as a farmer. But he was too well known, and accepted a position as President of Washington College.

While there – the most famous general on the side of the South – expelled white students for violently attacking local black men. He worked to establish state-funded schools for black people. And he even scolded Jefferson Davis, who had been the leader of the Confederates, asking for “kindness.”

Could it be, that as Lee aged, his heart opened up to justice and racial equality?

It’s hard to tell, but one thing definitely did happen to Lee’s heart – it failed.

Through the war years, Lee would often complain of chest pains.

In the fall of 1870, Robert E. Lee suffered a stroke and died 2 weeks later in Lexington, Virginia. He was only 63 years old.

Over the decades, America’s view of Robert E. Lee has changed. In 1907, on the 100th anniversary of Lee’s birth, then President Theodore Roosevelt said Lee was an example of great courage and outstanding leadership.

Today, some believe the “myth” of Robert E. Lee has been part of a long public relations campaign to remove any guilt from the southern states.

Regardless of how history will ultimately judge this complicated man, there is no doubt that Robert E. Lee knew how to lead with humility and determination – and perhaps more importantly – the fortitude to understand that losing is not always a bad thing.

The U.S. Civil War killed more Americans than any other war since. Estimates range as high as 800,000 (compared to 58,000 for the Vietnam War). President Abraham Lincoln won the war but had precious little time to enjoy his victory. He was assassinated just 6 days after Robert E. Lee surrendered. (Lee surrendered on April 9, 1865 and Lincoln was murdered on April 15).

Robert E, Lee will continue to be a controversial figure, but he demonstrated that none of us are all good or all bad, and that our decisions are based on what we feel is best, at the time we make them. 

3 thoughts on “How to Lead in a Losing Cause – Lessons from the Real Robert E. Lee

  1. There is a sad tendency of common people (and sometimes modern historiography) to judge past people with present moral standards. One cannot do that, these people lived in a different moral environment and should be judged by their standards, and not ours. Your article is important to show the contradictions and, therefore, human character, of Robert E. Lee. I was aware of this due to a Gettysburg visit I did in 2005 and learned how respected he is. It is just sad that common propaganda is destroying this respect. Nice text.

    Liked by 5 people

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