The Top 15 Army Leadership Failures Of All Time

Today, I’m going to share the top 15 Army Leadership Failures of all time, as I see it.

While the United States has the greatest Army in the world, there have been failures. After all, no military system is perfect and when you mix the methods and styles of leaderships, you are going to have mistakes.

Some mistakes have cost many lives. While it is not something we like to discuss, we must.

It is by examining failures that we learn how to not make the same mistakes. Hopefully, Army leaders have learned and will not be caught in the definition of insanity – doing the same thing over and over and expecting different results.

Top 15 Army Leadership Failures of All Time

What you will see below is my top 15 list. Some of these failures are the result of one particular leader while others are the fault of multiple leaders.

So, starting at #15, I will go through these top Army Leadership Failures up to #1. If you have a different opinion, feel free to leave that opinion in the comment section at the end of this post.

#15: The Punitive Expedition

This Army failure occurred between March of 1916 and February of 1917. The Mexican Revolution was underway and Pancho Villa was angry with the United States because they were supporting his political rival, Venustianzo Carranza.

Villa was attacking U.S. interests in Northern Mexico and suddenly he and his men attacked Camp Furlong and Columbus, New Mexico.

Commanding General Frederick Funston recommended a pursuit of Villa into Mexico. United States President Woodrow Wilson agreed and Brigadier General John Pershing was given the mission to hunt down and capture Pancho Villa.

More than 10,000 men were deployed for this issue. There was no support from the head of the Mexican government…. Carranza.

Actually, he came out in force against Pershing and the U.S. Army too. Essentially, during this whole expedition, Villa was never captured, but many of his men were killed or captured.

The head of the Mexican government would not accept Pershing and his forces being in the country of Mexico. Too many United States Army forces were used in a situation that shortened forces in other needed areas.

The good that did come from it was the experience gained, but the bad was the fact that the Mexican government gained a huge disrespect for Americans.

What we should have done is guard our border towns better and trap any raiders trying to attack them.

Pershing declared the mission a success, but where was Villa? Pershing was following orders, so the leadership failures were in Washington. It was an Army leadership failure.

#14: Pickett’s Charge

Some may say this shouldn’t be in the list because the failure was on the part of the Confederate Army.

I beg to differ. At that time in American history, the United States had two armies.

  1. A Union Army
  2. A Confederate Army

They were at war against each other.

This failure came on the last day of the Battle of Gettysburg, and many would claim this failure cost the Confederates the War even though it did drag on further.

Days prior, General Robert E. Lee had divisions try to flank the Union forces in Gettysburg only to be driven back.

The Commander of the Union forces was Major General George Meade. In looking at the methods used by Lee, Meade predicted that he would now attack the center. General Lee consulted with Lieutenant General James Longstreet, and they made a plan.

Major General George Pickett would take troops down the very center while Brigadier General J. Johnston Pettigrew would take troops on Pickett’s left and also down the center.

Major General Isaac Trimble’s artillery would weaken the Union forces and also support the right flank.

All in all it would have been a great plan if run at the start of the Gettysburg Battle, but it was just too easy to predict. The Union was ready and Confederate soldiers laid in heaps of rotting corpses. This failure was huge.

#13: Battle Of Fort Donelson

This failure in Army leadership also falls on Confederate forces. The two leaders that I see in major failure were the former Secretary of War and governor of Virginia, John Floyd and Brigadier General Gideon Pillow.

They were to defend Fort Donelson, but as Union forces moved in, Floyd turned command over to Pillow so he could escape and Pillow did the same, turning command over to Simon Buckner.

Both of these men ran and left others behind. Because these men had so many political allies, they were forgiven. With leaders like these, no wonder the Confederates lost the Civil War.

#12: The 2nd Battle Of Lacolle Mill

Lacolle Mill is located in Quebec, Canada. The year was 1814 and it was the War of 1812 against the British who would not lose their control over Canada.

Major General James Wilkinson took 4,000 soldiers and artillery to drive the British out of Lacolle Mill. The British had 80 regulars and approximately 400 reinforcements.

It should have been a simple mission for the American Army. Simply put, after launching artillery with no success and being charged at with bayonets, Wilkinson became disheartened and retreated. Wilkinson was relieved of command one month later.

#11: The Siege Of Charleston

It was evident that the British were going to focus on the Southern States in the Revolutionary War.

The Continental Army did not send defenses to cover areas outside of Charleston, South Carolina and Major General Benjamin Lincoln had over 5,000 troops within this locked area.

It was a strong lesson for Americans when British ships led by Sir Henry Clinton overtook Charleston forcing a surrender. It was the largest surrender of American troops in the Revolution.

#10: The Battle Of Kasserine Pass

Major General Lloyd Fredendall was leading a very inexperienced U.S. II Corps into Northern Africa early in World War II.

As soldiers and equipment moved through this small gap in the mountains of Tunisia, the German forces led by Field Marshall Erwin Rommel routed the American and allied forces.

Going into battle unprepared and unaware was the primary failure in this battle. Forces did regroup and were able to revenge the loss. But this failure should not have happened at the start.

#9: Abu Gharib

This failure put a huge black mark on the United States Army and the CIA. It was headline news when it was released that prisoners at the prison at Abu Gharib were tortured and abused.

What has always been a question of mine is why leaders were only removed and demoted and soldiers were sentenced to prison. The fact is: the United States is far better than we showed in this and torture and abuse is not the answer to gain intelligence.

Hopefully nothing like this ever happens again.

#8: The Surrender of Fort Detroit

During the War of 1812, American forces had tried to take the Brits out of Canada, but were unsuccessful.

Holding Fort Detroit was important, but Brigadier General William Hull was bluffed. The British with some Indians came upon Detroit and gave Hull the impression they had more force than they really did.

He handed Detroit over with barely a fight. One British shell fell in the Fort and Hull against all advice, raised the white flag of surrender. The Americans had much more firepower than the attackers and could have easily held out.

#7: Operation Eagle Claw

It was an operation I remember clearly. It was 1980 and the goal was to rescue 52 hostages being held in Iran.

It was a Joint operation and one of the first for Delta Force. President Jimmy Carter was desperate to free these hostages, but the plan was terrible.

Originally, 8 helicopters were sent but only 5 arrived to the staging area in operational condition.

During the original plan, if less than 6 helicopters arrived, they would abort the mission. So the advised abort was called and the President agreed. In the abort, a helicopter crashed into a plane killing 8.

There are a number of reasons it failed:

  • Planning

  • Weather

  • Pilot training

  • and the Command structure

This operation has been a learning experience for many.

#6: The Crater

The commander was Major General Ambrose Burnside and it was during the Civil War when the idea was made to trench under the Confederate fort and set explosives to break the defenses.

The explosion worked but Burnside had chosen a company of troops that were too drunk to attack. Instead of going around the crater made by the explosion, the soldiers went in the crater where they were sitting ducks for Confederate guns.

Shouldn’t there be an organization, Mother’s Against Drunk Warfare?

#5: The Bay Of Pigs Invasion

While not necessarily an Army operation, I had to put this on the list.

Anti-Castro exiles living in the U.S. were recruited to form a unit to overthrow the Cuban leader Fidel Castro. In 1961 with John F. Kennedy’s approval and the CIA’s leadership and invasion was underway. But Castro and Che Guevara were warned well beforehand from Cubans in Florida.

They were prepared with extreme firepower and the United States looked foolish. It has taken years for relations to get better with Cuba because of this huge failure.

#4: The Battle Of Antietam

The major failures in this Civil War battle came from Major General George McClellan of the Union.

Robert E. Lee used all his troops, but McClellan was conservative and as such, casualties were immense.

If McClellan would have used his full strength, Lee probably would not have been able to withdraw and regroup.

The lesson? If you have the troops and equipment, use them.

#3: The Battle of Bataan

While General Douglas MacArthur made many great military decisions, Bataan was one of his worst. The Philippine Islands were an important stronghold during the World War II Pacific Theater.

The Japanese were going to all means to take the Philippines. MacArthur decided to take all forces to the Bataan Peninsula, which was similar to putting cookies in a jar for the Japanese.

It was inevitable that the Japanese would force a surrender as they closed the net around the Americans.

General MacArthur escaped by orders leaving other Army commanders in charge. This led to the Bataan Death march that was devastating.

#2: The Battle Of Bladensburg

It is known as the Greatest Disgrace Ever Dealt To American Arms. It was the War of 1812, and Brigadier General William Winder was the lead commander.

Because of Napoleon being abdicated, the British took a hard approach toward the United States. Winder requested that Secretary of War John Armstrong deploy militia to the area of Bladensburg, Maryland, but Armstrong said no.

As the British moved in, Winder was operating with minimal soldiers. People in Washington were packing just in case.

The American Army forces fought gallantly in Bladensburg, but they did not have the means to hold. The result?Washington D.C. was burned.

The failure ultimately was on the Secretary of War, John Armstrong.

#1: The Battle Of The Little Big Horn

Many still ask, “What was Custer thinking?”

George Armstrong Custer took 700 soldiers into a bloodbath. He should have taken Gatling Guns, but he didn’t.

This Army leader’s pride was too much. He thought it would be an easy battle, but the Native Americans showed up in force.

Major Indian leaders including Crazy Horse, Sitting Bull and Chief Gall used upwards of 2,000 warriors against 700 soldiers.

The Little Big Horn area was a field of American Army blood.

I have visited this site and you can just smell the death that happened there. I rate this as the biggest Army Leadership Failure in military history.

Final Thoughts

Yes, failures have happened and we should not dwell on them, but we do need to learn from these failures.

Do you agree with this list of the top 15 Army Leadership Failures of all time? What are your thoughts? You can leave comments, questions and opinions below. Thank you.


chuck holmes

Chuck Holmes
Former Army Major (resigned)

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1 thought on “The Top 15 Army Leadership Failures Of All Time”

  1. I believe the current situation in Afghanistan August 2021 will eventually be added to this list and will probably go down as one of the greatest failures of leadership ever.

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