Historical Leadership Failures: Lessons from the Most Infamous Blunderers

Hats of military, religious and monarch leaders with thumbs down main

Incompetent leaders are unqualified, bumbling, and incapable of fulfilling their duties, and history is replete with such figures. Quintus Servilius Caepio, for instance, demonstrated that even the formidable Roman army had its blunderers. Emperor Caligula’s bizarre declaration of war on the sea remains a notorious example of folly. King John’s mismanagement led to the loss of significant French territories and the forced signing of the Magna Carta. Pope Celestine V, despite his kind nature, proved to be an ineffective pope. Both the Union and the Confederacy suffered under inept generals during the Civil War. Additionally, a series of ineffective presidents before and after the Civil War exacerbated already difficult situations, highlighting the far-reaching impact of poor leadership.

Different Kinds of Lousy

There have been some truly horrible leaders in world history. Adolf Hitler and Joseph Stalin are two that immediately come to mind. We are concerned with a certain kind of lousy this time.

An incompetent leader is unqualified, bumbling, and incapable of doing their job. A rocket scientist can be an incompetent brain surgeon.

Incompetence would be not showing up and the inability to do your job when you do. A good leader has the respect of their support team. Good leaders can handle unexpected events and adversity. A bad leader can find a way to lose even if their opponent is woefully overmatched.  

Horrible Military Leaders 

Ancient Rome created an empire with a skillful use of its military. There were some bad apples. 

Quintus Servilius Caepio was a thief, a lousy general, and a snob. A more qualified general (not a member of the Roman elite) carefully negotiated with a dangerous enemy. Quintus decided to attack. The result was a slaughter; over a hundred thousand Romans died.  

Santa Anna was an excellent survivor of the convoluted politics of newly independent Mexico in the mid-19th Century. Santa Anna had much less ability as a military leader. He “won” the famous battle of the Alamo. The Texans held on for over ten days at a poorly defended fort. The victory cost the Mexicans hundreds of avoidable casualties.  

The American Civil War had incompetent generals on both sides. George McClellan knew how to build an army. He had a lot of problems using it. Braxton Bragg was a favorite of Jefferson Davis, the president of the Confederacy. No one else had much respect for him, including most Civil War historians. He had lousy leadership skills and repeatedly failed on the battlefield. 

Incompetent Popes 

Jesus had an ironic choice as the leader of the apostles. Peter repeatedly misunderstood Jesus’ ministry. He had multiple crises of faith. He even denied knowing Jesus after his arrest. 

Christianity became a successful religion all the same. There still have been some lousy popes over the last two thousand years. Many were corrupt. Some were just plain incompetent. 

Pope John XII (954-964) became pope at age eighteen. He spent most of his papacy sowing his wild oats. We have many tales of adultery, drunkenness, and murder. Rumor has it that he died in the bed of another man’s wife. Surprisingly, he managed to stick around for ten years!

Pope Celestine V (1294) was a pious elderly monk. He was an incompetent pope. Celestine knew his inadequacies. He did not want the job. The new pope did not live in Rome. The King of Naples held the true power. No one respected Celestine’s authority. He resigned after a few months.  

Pope Clement VII (1523-1534) was a weak pope at an inconvenient time. The Protestant Reformation challenged the supremacy of the Catholic Church. A strong leader would have stepped up and reformed the Church. Reform would have to wait for better leadership.

Lousy Monarchs  

We had lots of monarchs. Some reigned for a long time. Many failed the leadership test. 

The Roman emperor Caligula (37-41) was cruel, unstable, and reckless. A famous Roman historian claimed Caligula tried to make his horse consul (a powerful governmental position). He led an ill-fated campaign to defeat Britain that failed before he arrived. Caligula instead declared war on the sea with seashells for war booty. His guards eventually assassinated him.  

Robin Hood is a fictional tale. King John did exist and was a horrible king. He quickly lost most of the French lands his family had conquered. John then had to spend more time in England, which caused many problems. The situation became so bad that nobles rebelled. John died fighting in a civil war. The best thing that came from this was the Magna Carta (1215). 

Christian VII of Denmark (1766-1808) was mentally unstable. He had a brutal childhood. Christian suffered from hallucinations. People often were unable to understand his speech. Diplomats complained about him smacking them in the face. Others ruled in his place while he acted like a child. He often reigned in name only, which most people appreciated. 

American Presidents 

The United States had forty-five presidents (as of 2024). One president served separate terms. His daughter Ruth gave her name to a candy bar. We had our share of incompetents. 

The years before and after the Civil War were a prime breeding ground for horrible leadership. James Buchanan made divisions over slavery worse and did little when the South seceded. After the war, Andrew Johnson was a racist and incompetent president. Ulysses Grant was a fine general. He was a poor president. Grant’s administration had multiple scandals. 

Herbert Hoover also shows some people have fine careers while failing as a president. He helped to feed Europe during World War I. Hoover, however, could not handle the Great Depression. Donald Trump might beat them all, including his failures in dealing with COVID-19. 

The United States did have its share of incompetent presidents and generals. World history shows that we had a lot of company. History has all kinds of leaders!

Teach and Thrive

A Bronx, NY veteran high school social studies teacher who has learned most of what she has learned through trial and error and error and error.... and wants to save others that pain.