Ask ChatGPT: Leaders Who Failed to Plan Before War

In the previous post I discussed the importance of analysis for victory. Today, I asked ChatGPT to give some examples of such failures. This is part of an on-going series where I ask ChaptGPT to elaborate on some aspect of what I write and evaluate ChatGPT as a source. Its called Ask ChatGPT and I’ll make sure you know it is the AI writing the post and not me. Also, I’ll include the prompt I used.

Here is the prompt: Give me some examples of battlefield commander allowing their bad analysis to lose the battle or war.

Throughout history, many battlefield commanders have allowed their weaknesses—whether arrogance, indecisiveness, poor intelligence, or underestimation of the enemy—to cost them a battle or even an entire war. Below are some notable examples of military leaders whose personal or strategic failings led to defeat.

1. George Custer – The Battle of Little Bighorn (1876)

Weakness: Arrogance and Underestimation of the Enemy

At the Battle of Little Bighorn, Lt. Col. George Armstrong Custer led the 7th Cavalry Regiment into an engagement against a much larger force of Lakota Sioux, Northern Cheyenne, and Arapaho warriors. His overconfidence and reckless underestimation of the enemy led to total disaster.

Mistakes that led to his defeat:

Failed to recognize the fighting capability of his opponents, assuming they would scatter rather than stand and fight.
Ignored intelligence reports suggesting that the Native American force was much larger than anticipated.
Divided his forces into three smaller units, making them vulnerable to encirclement.
Rejected offers of reinforcements, believing his regiment alone could handle the battle.

Outcome:
Custer’s entire force was annihilated, with him and 267 of his men killed. His refusal to properly assess enemy strength, coupled with his reckless attack, sealed his fate and made Little Bighorn one of the most famous military blunders in U.S. history.

2. Napoleon Bonaparte – The Russian Campaign (1812)

Weakness: Overconfidence and Logistical Failures

Napoleon, one of history’s greatest strategists, suffered a humiliating defeat in his 1812 invasion of Russia due to his own arrogance and failure to account for logistics.

Mistakes that led to his defeat:

Underestimated Russian resistance—assuming a quick, decisive victory.
Ignored supply chain problems, leading his Grand Army to suffer from starvation and lack of supplies.
Failed to account for the Russian “scorched-earth” tactics, which left his army without food or shelter.
Did not prepare for the Russian winter, which killed thousands of his troops.

Outcome:
Napoleon lost over 400,000 soldiers—most to starvation, exposure, and exhaustion. His Grand Army, which once ruled Europe, was left in ruins. His failure to recognize the limits of his own forces and the severity of Russian resistance marked the beginning of his downfall.

3. General Paul von Hindenburg and Erich Ludendorff – The German Spring Offensive (1918)

Weakness: Short-Term Thinking and Poor Strategic Planning

During World War I, Germany launched the Spring Offensive (Kaiserschlacht) in 1918, an all-out attack on the Western Front. Generals Paul von Hindenburg and Erich Ludendorff believed this was Germany’s last chance to win before U.S. reinforcements arrived. However, poor planning and logistical weaknesses doomed the offensive.

Mistakes that led to their defeat:

Over-reliance on “stormtrooper” tactics—small, fast-moving infantry units that advanced quickly but lacked sustainability.
Failed to plan for supply logistics, meaning advancing German forces outran their support and ran low on food, ammunition, and reinforcements.
Ignored the exhaustion of German troops, expecting them to keep attacking despite suffering enormous casualties.
Did not anticipate the Allied counteroffensive, which eventually pushed Germany back and led to the end of the war.

Outcome:
The Spring Offensive collapsed, leaving Germany in a weaker position than before. By November 1918, Germany was forced to surrender, and Ludendorff fled into exile, disgraced by his failures.

4. Confederate General John Bell Hood – The Franklin-Nashville Campaign (1864)

Weakness: Recklessness and Disregard for Troop Well-Being

During the American Civil War, Confederate General John Bell Hood was known for his aggressive and reckless tactics. However, his lack of strategic foresight and overconfidence led to disaster in the Franklin-Nashville Campaign.

Mistakes that led to his defeat:

Recklessly launched a frontal assault at the Battle of Franklin, sending his exhausted troops against well-fortified Union defenses.
Ignored warnings about Union reinforcements, assuming his depleted army could still achieve victory.
Failed to properly equip or supply his forces, leading to starvation, desertion, and exhaustion.

Outcome:
Hood’s army was decimated, losing 6,000 men in the Battle of Franklin alone. At the Battle of Nashville, his army was completely destroyed, ending Confederate resistance in the Western Theater. His leadership was widely condemned, and he resigned shortly after.

5. Saddam Hussein – The Gulf War (1991)

Weakness: Hubris and Miscalculation of U.S. Military Capabilities

Saddam Hussein’s decision to invade Kuwait in 1990 ultimately led to the Gulf War (1991), where his lack of strategic understanding and miscalculation of U.S. military power resulted in total defeat.

Mistakes that led to his defeat:

Underestimated the global response—Hussein believed the U.S. and its allies would not intervene or would struggle to mobilize effectively.
Misjudged American air superiority, failing to protect Iraqi forces from devastating airstrikes.
Failed to anticipate the rapid “Shock and Awe” U.S. campaign, which quickly destroyed Iraqi defenses.
Ignored warnings to withdraw from Kuwait, instead making empty threats and alienating potential allies.

Outcome:
The U.S.-led coalition obliterated Iraqi forces in just 42 days. Hussein’s army was forced to retreat, and he remained in power only due to the decision not to remove him. However, his failures in the Gulf War set the stage for his eventual overthrow in 2003.

Conclusion: Weaknesses in Leadership Cost Battles and Wars

Each of these commanders suffered defeat because of their own weaknesses—whether arrogance, recklessness, strategic blindness, or underestimation of the enemy.

Custer assumed his superior training would allow him to defeat a much larger force.
Napoleon ignored logistics and failed to account for the Russian winter.
Hindenburg and Ludendorff wasted Germany’s last offensive chance due to bad planning.
Hood destroyed his army through reckless frontal assaults.
Saddam Hussein underestimated U.S. military capabilities and global response.

Sun Tzu warns: “If you do not know your enemy nor yourself, you will be imperiled in every battle” (Sawyer, 1994, 84).

Each of these leaders ignored key strategic factors that should have been obvious—and their armies paid the price. Their failures serve as enduring lessons in why strategic analysis and humility are critical in warfare.

Strategy in Brief