7 Of The Worst Military Leaders In History, That You Didn’t Know About

Some were corrupt, others inept, and some just plain old stupid- these are the worst military leaders in history.

There are military leaders who are nasty, vicious, and insane. However, we discovered some of the worst military leaders in human history, who may or may not have had a place in the military.

Quintus Servilius Caepio

Maps of Cimbrian and Teutons invasions Cimbri and Teuton defeats Cimbri and Teuton victories, by Pethrus, licensed under CC BY-SA 4.0 via Wikimedia Commons

The Roman Empire has a long, proud tradition of producing some of the finest generals in human history- and just as many of the worst. Quintus Servilius Caepio takes the cake amongst the worst Roman generals ever to take command of a legion though.

Caepio was born into a noble family and became consul in 106 BC. Self-interested and thoroughly corrupt, he allied himself with a skilled orator to sway the public into accepting a law that ensured only Senators could be jury members, effectively stripping the working class of any power over legal proceedings. The law would eventually be struck down, but Caepio’s corruption wouldn’t end there.


Appointed a Roman general, Caepio was enroute to fight the Cimbri, a tribe of Germanic warriors, when he came across sacred temples in the city of Toulouse. Caepio plundered a whopping 50,000 fifteen-pound gold bars and 10,000 fifteen-pound silver bars- a sum worth over 11 billion dollars today.

Caepio’s plunder was shipped to Rome, but on its way a group of brigands attacked the convoy carrying the loot and stole all of the gold, leaving only the silver to make it back home. It’s widely believed that Caepio had hired the brigands himself, and split the loot between himself and the group of mercenaries at a later point.

Boums Lake in Haute-Garonne, one of the many lakes near Toulouse suspected to have held the ‘cursed’ riches, by AchilleT, Public Domain via Wikimedia Commons

Having plundered billions in gold, Caepio proceeded to link his forces with those of General Gnaeus Mallius Maximus in anticipation of battle against the Cimbri. However, upon learning that General Maximum was of a lower social class than him, he refused to accept his command or to even share camp with him. Thus Caepio moved his legions away from Maximus’ camp and plotted what to do with the Cimbri on his own.


Maximus was by all accounts a capable military commander, and had the wisdom to know when to fight and when to negotiate. With the Cimbri, Maximum decided to negotiate, and was in advanced stages of diplomacy when Caepio got wind of the proceedings. Convinced the Cimbri were weak, Caepio decided to attack- without Maximus’ forces.

Caepio’s forces were utterly annihilated, forcing him to flee for his life. However, the brutal defeat of his legions emboldened the Cimbri to attack Maximus’ own camp. Maximus attempted to rally a defense, but was overwhelmed by the Cimbri. In the end, over 80,000 Roman infantry and 40,000 mercenaries and Roman cavalry were killed, marking this one of Rome’s worst defeats ever.

Maximus would lose all of his sons in the battle, and upon returning to Rome was exiled from the empire for his defeat. Caepio too was forced into exile and stripped of his Roman citizenship, as well as fined 15,000 talens of gold. However, Caepio managed to evade the fine and fled to Asia Minor, where he would live in abundant luxury thanks to the gold he had stolen in France.


Racist, corrupt, and stupid- Quintus Servilius Caepio left his mark on Roman history, though probably not the way he dreamt of. In all likelihood though, he could probably care less.

Our next worst general was as inept and vain as he was cowardly.

Gideon Pillow

General Gideon Pillow, Public domain, via Wikimedia Commons

It’s a commonly held falsehood that during the American civil war, the Union had the advantage in materials while the Confederacy had the superior generals. In truth, the Confederacy did field better commanders in the east, but in the west the Union had far superior leaders. Confederate General Gideon Pillow was by far the worst military commander in the western theater of the civil war.


His career as a terrible military leader began during the Mexican-American war. He was appointed to the rank of Major General by his close friend President James K. Polk, despite having no military experience prior to this. Pillow was nonetheless made commander of a unit of volunteers and dispatched to northern Mexico, under the command of General Zachary Taylor.

Unimpressed by the man, Taylor took Pillow’s forces for an attack on Monterey, leaving Pillow behind to garrison the army’s depot at Camargo. Pillow immediately ordered the defenders to construct fortifications- facing the wrong way.

Pillow’s ineptitude would cost lives though at the battle of Cerro Gordo. Tasked with launching a secondary attack on Santa Anna’s right flank to destroy his artillery, Pillow chose to reinterpret his orders and instead launched an attack at the enemy’s center. Pillow’s forces were exposed to withering fire, costing many lives.

1840s newspaper cartoon depicting Pillow’s self-promoting attempts to discredit Mexican–American War commander General Winfield Scott-a pun of Pillow’s name, Public Domain via Wikimedia Commons

Pillow was sent home on leave after the battle, and wasted no time in bragging about his exploits. Tennessee veterans returning home however were quick to correct the record, calling Pillow a coward and an idiot. Despite this, Pillow was returned to the war and promoted to Major General by his good friend, President Polk.

As the war progressed, Pillow would infuriate his fellow generals by writing fanciful stories to the press aggrandizing his own successes while downplaying those of his compatriots- even outright stealing their glory. Pillow nonetheless denied the accusations, and despite being court-martialed was saved by once more, his friend President Polk.

Pillow’s greatest idiocy however would come during the American civil war, when he single-handedly opened up the southern flank for invasion by the Union.


Pillow was tasked with the defense of Fort Donelson, a strategically critical strongpoint on the Mississippi river that threatened to open up the deep south to Union forces if destroyed.

General Ulysses S. Grant had carefully surrounded the fort and cut it off from reinforcements before launching an attack. Surrounded and under fire from enemy ships on the Cumberland River, Confederate forces attempted a breakout so they could reconsolidate and mount a stronger defense.

Battle of Fort Donelson, by Kurz & Allison., Public domain, via Wikimedia Commons

The Union’s right flank and center was thrown into disarray and forced to retreat, opening up a path for the Confederates to slip away and join reinforcements. Pillow however declined to cede ground, and believed that he could hold off another Union attack on his own. Despite being implored to retreat by his men, Pillow ordered them back into their fortifications.


Grant took the opportunity to mount a brutal counter-attack that crushed the Confederate defenses. Only a few thousand troops managed to escape the Union onslaught, with Pillow alongside them, having slipped away in the dead of night.

Pillow’s foolishness handed the Mississippi over to the Union, and guaranteed them access to the very heart of the Confederacy.

Our next worst military leader in history was as bad a general as he was a dictator, almost single-handedly destroying his own country.


Francisco Solano Lopez

Francisco Solano Lopez in 1870, Public Domain via Wikimedia Commons

The eldest son of dictator Carlos Antonio Lopez, Francisco seized power shortly after his father’s death. His father had left him in command of a stable Paraguay with a relatively strong military, and with warnings to not use military force to settle diplomatic disputes. Francisco paid literally zero attention to his father’s warnings, and immediately tried to put himself at the center of Latin American politics- backed up by his military.

With Brazil to the north and the east, and Argentina to the south, Paraguay’s survival counted on the nation remaining neutral between the two South American superpowers. However, sensing an opportunity to raise his own standing in South America, Francisco placed himself smack dab in between the two rival powers as he intervened in the Uruguayan civil war, in which both Brazil and Argentina had their own stakes.

Francisco hoped to help resolve the civil war and thus make himself a political star, but instead he managed to get his country into war with Brazil and pissed off the Argentinians. Flanked by Brazil in the east, Francisco took his idiocy to the next level by demanding that his troops be allowed to station themselves in the Argentine province of Corrientes.


Argentina however had no wish to go to war with Brazil, and Francisco’s incursion on their soil instead prompted Argentina to join a three-way alliance with Brazil and Uruguay to destroy Paraguay.

Death of Francisco Solano López, by Adolfo Methfessel, Public domain, via Wikimedia Commons

Let’s take a moment to appreciate Francisco’s staggering foolishness: wishing to take center stage in South American politics he tried to end the Uruguayan civil war, and instead prompted Uruguay, Brazil, and Argentina to declare war on him

The resulting war would be catastrophic for Paraguay, resulting in as much as half the population dying.


Francisco was forced into hiding in the mountains and hills, where he tried to wage an unsuccessful guerilla campaign against the allied occupiers. Seized by extreme paranoia, he ordered the execution of any soldier or civilian who spoke of surrender. Francisco Solano Lopez would end up dying when he was gunned down trying to charge a group of allied soldiers with a sword.

Our next worst military leader was so out of touch, he completely disregarded the impact technology had on modern warfare- leading to some of the greatest single-day losses of life in the history of war.

Sir Douglas Haig

Sir Douglas Haig, by Elliott & Fry, Public domain, via Wikimedia Commons

Sir Douglas Haig was made chief of staff of the British Expeditionary Force as it joined World War I. At the time Britain was a prosperous nation, an economic and military powerhouse which had enjoyed unrivaled supremacy for hundreds of years. Haig would be the nation’s first step towards its tumble from glory.


The opinions of historians differ on Haig, but most agree that he is part of the military leadership that led to the pointless slaughter of hundreds of thousands of British soldiers. Refusing to believe that the machine gun had made traditional combat obsolete, Haig was behind the tragedy that was the Battle of the Somme. On July 1st, 1916, he ordered 110,000 British soldiers over the top. Such an overwhelming attack would indubitably secure victory and break the German army’s center.

20,000 would die in one day, and another 40,000 would be wounded. Over half of the first attack had returned as a casualty or not at all. Despite this, Haig had the nerve to write in his personal journal that the scope of the attack and the wide front made the casualties perfectly acceptable and expected.

Convinced that the attack had weakened the enemy significantly, Haig ordered the British army back over the top again. And then again, and again, and again, for four months straight until nature took pity on the massive loss of British life and winter conditions made further attacks impossible.

Men of the 10th (Service) Battalion, East Yorkshire Regiment of the 31st Division marching to the front line, 28 June 1916, by Ernest Brooks, Public Domain via Wikimedia Commons

Haig was not just stubborn, he was living in a dream world of denial. Despite the massive casualties inflicted on his forces by German machine guns, Haig believed that the machine gun was overrated and not responsible for his great losses.

He believed so little in the machine gun that as each new attack on the Germans was launched, he brought up cavalry reserves, fully expecting the army to punch a hole through the German front which would be exploited by Haig’s horse-born cavalry.

Perhaps the luckiest soldier in the British army at the time were the cavalry- which on their own would be decimated by modern firearms, but thanks to the British army’s inability to break through German defenses, never had to undertake their own suicidal charge.


Haig was so out of touch with modern combat, that he failed to learn lessons from even 100 year old wars- and insisted on his men charging forward at a moderately fast walk, so that their lines could be better maintained and order and discipline enforced. All this did was make British soldiers easier targets for German riflemen and machine gunners. But despite half a million casualties, Haig refused to change tactics.

In 1917 the French army was all but obliterated. America had just joined the war and the British government wanted to wait for US forces to arrive in number before any new campaigns against the Germans. Haig however was eager for another Somme-like battle, only with greater numbers of troops in even worse terrain.

Haig lobbied his allies in the British government though and got approval for yet another offensive across Flanders, in what would become known as the Battle of Passchendaele. Rather than wait for the American Expeditionary Force, Haig ordered a general attack against the German line.

Chateauwood – Battle of Passchendaele, by Frank Hurley, Public domain, via Wikimedia Commons

The terrain decisively favored the defenders, with the landscape consisting of wet, muggy swamp-like conditions made even worse by the moon-scape cratering effect of thousands of pieces of artillery. Massive shell holes had filled in with water, and it’s certain that more men drowned in this land battle than in any other in history.

The absolute slaughter of British forces prompted Winston Churchill to comment that Haig had “wore down alike the manhood and the guns of the British army almost to destruction.” It’s rumored that Haig’s chief of staff was driven to the front and upon seeing the terrain for the first time, broke into tears and said, “Good God, did we really send men to fight in that?” His driver’s response was simple: “It gets worse farther on up.”

250,000 British would become casualties in that battle, prompting the British army to be reduced in strength significantly. Without the intervention of the United States, the entire western front would have collapsed in the year to come, securing a German victory.


Haig would remain in command of the British Expeditionary Force, but after the war would be lambasted for his failure to understand modern combat and the technological innovations that had forever changed it. Today, while some attempt to defend the man’s legacy, most historians agree that he remains one of the worst military leaders in human history.

Our next worst military leader is best known for his failures after a battle than during it.

Erich Ludendorff

Erich Ludendorff in 1915, licensed under CC BY-SA 3.0 via Wikimedia Commons

Few military leaders have the distinction of being considered amongst the worst military leaders in history for the things they did after the fighting was over, rather than during it. Erich Ludendorff is amongst that number.


By all accounts Ludendorff was a capable, if not superior, military leader during World War I. He oversaw the mostly successful Operation Michael, a German offensive that kicked off the German Spring Offensive of 1918.

However, he failed to tie together this operation with a grander strategic picture, leaving the Germans with little to show for their battlefield victories. He also helped secure victory against the Russian army at the start of the war in the Battle of Tannenberg.

Ludendorff’s failures began with his and German General Helmuth von Moltke’s alterations to the Schlieffen Plan, which was Germany’s plan for victory in a two-front war established in 1905. The plan called for a holding force to simply keep Russian troops at bay while fighting a defensive action.


The second part of the plan involved a massive flanking attack on French forces with overwhelming numbers, with an attack wave that would push through the north and then hinge down south into France’s defenses. Ludendorff helped weaken the plan by diverting the required troops from the western theater to the east, reducing the required 7:1 ratio to secure victory.

Western Front 1914; Schlieffen Plan of 1905. French Plan XVII, by Tinodela, Public domain, via Wikimedia Commons

Ludendorff also helped ensure America’s entry into the war by pushing for unrestricted submarine warfare against ships entering British waters, including the merchant and civilian vessels of foreign nations.

While the British were indeed hiding supplies inside ships carrying American civilians, unrestricted submarine warfare proved to be a strategic disaster that directly led to the entry of the United States into World War I, and Germany’s defeat. Cutting Britain off from war supplies was simply not worth the cost of losing the war due to overwhelming American numbers.


Ludendorff’s real failures however came at the end of the war, as the defeated German army was demobilized and sent home. Bristling with anger and indignation, Ludendorff stubbornly held on to the belief that Germany had in fact not been militarily defeated, completely failing to appreciate the strategic weight of America’s entry into the war.

While he may have been right had the United States not entered the war, the fact is the civilian population was already exhausted from years of war, and the resulting economic collapse of Germany as it shifted to total war mobilization. In fact, many soldiers on the front were eating better than some German civilians, and the war had quickly lost any form of popular support.

Undeterred, Ludendorff was instrumental in spreading the ‘stabbed-in-the-back’ myth, which painted Germany as having been stabbed in the back by Jews, Communists, and other hated minorities. It was them, and not the failure of the German military, that was responsible for losing the First World War. The general quickly became a zealous nationalist and helped set the stage for Hitler and his Nazi party.

Ludendorff (center) with Hitler and other early Nazi leaders and prominent radical German nationalists, April 1924, Bundesarchiv & Heinrich Hoffmann, licensed under CC BY-SA 3.0 via Wikimedia Commons

Despite later disavowing Hitler, Ludendorff had already helped set the stage for the atrocities of the Nazi party and for World War II. He’d also write a book that helped spur the nation back into a war frenzy with the Nazis at the leash with the publication of his book, The Total War, which argued that humanity existed in a state of perpetual war and thus nations should remain mobilized for war at all times.

Peace was merely a short interim period between wars, and only the nation that remained completely committed to war at all times could ultimately emerge victorious.

For helping bring about the horrors of the holocaust and World War II both, Erich Friedrich Wilhelm Ludendorff has the unique distinction of being one of the worst military leaders in human history.


Our next worst military leader was as brilliant as he was unfit for command.

George McClellan

George McClellan, by Mathew Benjamin Brady, Public domain, via Wikimedia Commons

Union General George McClellan is a perfect example of assigning the right man for the right job- unfortunately for the Union during the American Civil War, McClellan was the wrong man for the job.

McClellan was a decorated soldier and West Point graduate. He served with distinction during the Mexican-American War, and was sent as an observer to the Crimean war where he learned the importance of logistics for a modern army. This would prompt the genius of the man, as he would learn organizational skills which would be instrumental in the Union’s war effort against the rebellious Confederacy in the American Civil War.


At the outbreak of war McClellan was pursued by several states to command their militias, eventually accepting Ohio’s offer. A month later he would be given responsibility for the defense of Ohio, Indiana, Illinois, and later Western Pennsylvania, Western Virginia, and Missouri. Two weeks later he was made a major general in the Union army, second only to Lt. General Winfield Scott, general-in-chief.

McClellan immediately took to the task of processing the thousands of volunteers joining the army, as well as the logistical nightmare of outfitting and equipping the entire Union army. The secession of the southern states had wreaked havoc on the traditional logistics of the United States army, and the entire system had to be rebuilt from the ground up.

He set up routes of supply from new sources as well as training camps across the north for the rapidly growing Union army. McClellan would prove a strategic genius at fixing the logistical issues of the early Union forces, and the men under his command would always enjoy good food, high morale, and plenty of resupply.


However, as brilliant as McClellan was in logistics, he was equally timid about battle itself. McClellan scored two small victories in the territory that would become West Virginia, and was subsequently summoned to lead the Union army after its terrible defeat at Bull Run. Having been the only Union general with victories under his belt- no matter how small- McClellan was a national hero.

Maryland campaign, actions September 3–15, 1862, by Hal Jespersen, Public domain, via Wikimedia Commons

He then spent weeks fortifying the capital against Southern attack, building a series of forts and fortifications that made Washington utterly impregnable to attack. McClellan excelled at construction defenses- because he was absolutely terrified of the Confederacy.

General McClellan refused to take offensive operations against the Confederacy due to his belief that the Union was facing a massive army over 100,000 strong at the time- when in fact the Confederates had struggled to put together 35,000 troops for the offensive in Bull Run.


Over and over again through the course of the war, McClellan refused to seize the initiative and push any advantage he discovered, for he always believed he was vastly outnumbered.

This growing sense of extreme paranoia would end up robbing the Union of key victories which could have ended the war years before it did- with McClellan once refusing to advance on the Confederate capital, despite being close enough to hear the church bells ringing, because he was convinced a far superior force was ready to defend it.

In reality, McClellan rarely ever faced a battle where his forces didn’t outnumber the enemy 2 to 1. General Robert E. Lee would eventually figure out McClellan was a very timid commander and use this to his advantage, with bold offensives against the Union that relied more on McClellan’s paranoia about superior strength than any actual combat ability of the confederate forces involved.


McClellan would work to restore the morale of a seriously demoralized Union army after the staggering defeat at the second Battle of Bull Run, but would fail to secure victory against the Confederacy at the Battle of Antietam, believing once more that his strategic position was vastly inferior than it really was.

First Battle of Bull Run, by Kurz & Allison, Public Domain via Wikimedia Commons

Later commentators would observe that McClellan’s doctrine was extremely sound for a man fighting against a numerically superior foe- but as this was not the reality he faced, and all that McClellan’s timidness netted him and the Union was an unnecessarily long civil war and a spot amongst the worst military leaders in history.

Our next worst military leader was so bad, he was directly responsible for the establishment of another military leader as one of the greatest in history.


Pierre-Charles-Jean-Baptiste-Silvestre de Villeneuve

Pierre-Charles-Jean-Baptiste-Silvestre de Villeneuve, by E. T., Public domain, via Wikimedia Commons

Rising to the top of Napoleon’s naval ranks simply by virtue of being the only guy left alive, Pierre Charles Villeneuve began his naval career in Napoleon’s fleets by commanding one of only two surviving ships from the destruction of the Battle of the Nile. After that he was captured by the British when he landed at Malta and the island fell to the Royal navy.

Villeneuve was eventually released, and with other French admirals dead or having incurred Napoleon’s wrath, Villeneuve was suddenly one of the French fleet’s most senior officers. He was thus placed in charge of the French fleet at Toulon in 1804 with one simple mission.

Attack British holdings in the Caribbean so as to draw the British fleet there, thus opening up Britain to invasion over the Channel. With the British distracted in the Caribbean, he was then to rush back to the Channel to defend the French invasion. 

Battle pf Trafalgar, by Clarkson Frederick Stanfield, Public domain, via Wikimedia Commons

Villeneuve managed to draw the attention of Horatio Nelson and the British fleet, but then disobeyed orders by sailing for Cadiz instead of the Channel, where he was supposed keep the royal navy out of the Channel as the French army crossed it. Nelson was able to return to the Channel in time to stop Napoleon’s plans, and the British fleet would end up in control of the French coast for the remainder of the war.

Napoleon ordered Villeneuve to be relieved of command for his disobedience, and upon hearing the news, Villeneuve rashly decided to attack the British fleet directly. The legendary Battle of Trafalgar would result in an overwhelming British victory that established the Royal Navy as ruler of the high seas for 100 years, and propelled Horatio Nelson’s name to legendary status.

Featured image: General George B. McClellan with staff & dignitaries (from left to right): Gen. George W. Morell, Lt. Col. A.V. Colburn, Gen. McClellan, Lt. Col. N.B. Sweitzer, Prince de Joinville (son of King Louis Phillippe of France), and on the very right—the prince’s nephew, Count de Paris, Public Domain via Wikimedia Commons