British Field Marshal Sir Bernard Montgomery
Britain Field Marshal Sir Bernard Montgomery – If an American is making this list, then you know British General Montgomery is included toward the top. Most American’s gripe at the fact that he largely got in the way of General George Patton (who beat him to Messina during the invasion of Sicily, despite having to travel farther and through tougher terrain).
In this case though, his ability to navigate tough terrains quickly came to the help of no one. Of course, let’s give credit where credit is due and first recognize Montgomery’s victory at El Alamein in Egypt which earned him respect.
Operation Market Garden
But let’s also point out that it took him another seven months to drive the Germans out of North Africa. And then there’s also Operation Market Garden, which was his attempt to end the way and make it home for Christmas 1944, and instead resulted in 6,000 British airborne troops surrendering in Arnhem.
Even though is was resounding defeat, Montgomery did not see it the way the public and his leaders did. He called Market Garden “90% successful,” which prompter the Prince of the Netherlands to say, “My country can never again afford the luxury of another Montgomery success.” Ouch.
United States General George McClellan
Now that our British readers are fuming let’s take a look at an American commander who was even more in denial of his lack of ability to lead military forces effectively. Like Montgomery, McClellan will be remembered for his overly cautious approach to battle and lack of ability to pull the proverbial trigger.
The man considered a “Young Napoleon” trained the Union army in the Civil War into an extremely effective fighting force, then fought hard to keep them out of battle. Often ignoring or downright disobeying President Lincoln’s pleas to attack, McClellan finally placed the superior-in-number Union army into battle with the Confederates.
Battle of Antietam
On the eve of the Battle of Antietam he received a rare gift: the Confederate army’s battle plans! It’s the kind of come up that only comes around once in a blue moon. It indicated exactly where Confederate Commander Robert E. Lee was going to amass his troops and where he was going to strike.
Instead of properly leveraging the information about the enemy to his advantage like most military leaders would have, he slowly gathered his forces (that were double in size) and the result was the bloodiest day in American history (September 17) with 23,000 casualties. The general was sacked by President Lincoln two months later.
German Corporal Adolf Hitler
Don’t laugh but… actually go ahead and laugh all you want about the fact that British Prime Minister Winston Churchill use to joke about “Corporal Hitler.” This was the highest military rank he achieved before he arrogantly felt himself qualified enough to be Fuhrer and launched on of the biggest military fights in history.
Hitler had some of the most talented commanders warfare has ever seen at his disposal, but like Sadaam Hussein, he is guilty of ignoring their advice and taking command himself. Even before Operation Barbarossa starting going bad, which was effectively the turning point in the war, Hitler made some seriously poor choices.
Battle of the Bulge
It was his call to turn the German army South when they were less than 30 miles from Moscow, forever dooming Operation Barbarossa. His insistence on launching the Battle of the Bulge was a doozy too, as that hastened Germany’s defeat. As the war began going increasingly bad (largely from his strategic decisions) for Germany he became more paranoid about the loyalty and competence of his commanders.
Assassination attempts on Hitler were entirely internal efforts, as allied leadership wasn’t eager to kill the man who was often wrong and never in doubt (“Never interrupt your enemy when he is making a mistake.” – Napoleon). Hitler does deserve some credit though; he did kill Hitler.
United States Lt. Colonel George Armstrong Custer
Custer, Custer, Custer oh my dear, dear boy what were you thinking?! Custer was on track to go down as one of the most courageous commanders in history if it weren’t for one Little Big problem: The Battle of Little Big Horn. Instead, his legacy is making it onto this list.
Custer may have been brave having been decorated for valor and amassing an impressive record in the Civil War, but his tenacity as an Indian fighter would make him a modern-day war criminal. Conduct aside, Custer committed a series of leadership blunders that cost him and his entire command their lives.
Battle of Little Big Horn
On the morning of June 25, 1876 Custer unwittingly led his troops into a gathering of several Native American tribes. His men were weakened and in no condition to have to fight, having ridden their horses virtually nonstop for three days.
First, he sent his men into an attack after riding for he divided his men in half, and then with his just over 200 men he ordered an attack on a force of over 1,000. Without any reinforcements or big guns, and zero effort to reconnoiter the battlefield with his exhausted army Custer led his men to slaughter in the village by the Little Big Horn River.
French General Robert Georges Nivelle
Just about every German, British, and French general in WWI should be on this list, but since General Nivelle’s conduct is especially egregious, we’ll go ahead and single him out. Nivelle did successfully defend Verdun — a French victory — but he lost over half a million men doing it. So many died that the land still sometimes raises the bones of the fallen to this day.
Incorrectly assuming it was his tactics that won the Battle of Verdun (the German high command simply had enough of the proverbial meat grinder), he threatened to resign if the French leadership wouldn’t let him attack. Less than 10 days into the “Nivelle Offensive” in April 1917, the French had suffered a quarter million casualties with little to show for it. A full-scale mutiny nearly ensued that was only avoided when French leadership decided to sack Nivelle.
British General Sir Douglas Haig
Okay, we’ll go ahead and single out a WWI commander on all the aforementioned sides. For the British, we’re going after General Haig, primarily for his conduct at the Battle of the Somme. Just six months into obtaining command of the British Expeditionary Force (BEF), he ordered a massive offensive to help relieve pressure on French forces at Verdun.
The Battle of the Somme ensued, where Haig ordered 20,000 men to their slaughter (and another 40,000 wounded) on the first day of the battle. It remains the bloodiest day in British history. He produced another gem at the Third Battle of Ypres (or Passchendaele) where he wasted another 310,000 British youths without producing any substantial gains. To add another staggering number, consider that 800,000 men died under his command — almost double the amount of British killed in all of WWII.
German General Alexander von Kluck
You can blame the fruitless, bloody stalemate that was trench warfare on General von Kluck. In the early 20th century, the Germans developed the “Schlieffen Plan” — a how-to guide on defeating France. It called for a massive right hook through Belgium, and von Kluck was at the extreme right of this maneuver.
In August of 1914, Germany was kicking the hell out of the French and Expeditionary Force, and rather than envelop Paris from behind like the plan called for, von Kluck turned 13 miles in front of the French Capital. A gap in the German lines opened up, and each force tried to outflank each other all the way to the British Channel. With lines formed, and each side exhausted after experiencing extremely heavy casualties, the two sides settled in with little change over the next four years.
Mexican General Antonio López de Santa Anna
Like many on this list, Santa Ana’s country of origin (Mexico) see him as hero. But the “Napoleon of the West,” as he liked to call himself (one thing this list reveals is any comparison to Napoleon is the quickest way to find yourself being labelled as a bad commander), lost a whole lot more than he won.
Let’s start with the Alamo. Even though he won the battle, he emboldened resistance from Texans when a garrison was able to hold him up for 13 days despite an at least 10–1 advantage. Weeks later his entire army would be vanquished in a 15-minute battle where in the end he would find himself captured. Generals, stop trying to compare yourself to Napoleon; there can only be one!
United States General William Westmoreland
When it comes to the Vietnam War, there is plenty of blame to pass around among senior leadership in the United States about how the whole thing was handled, but commander of US forces General Westmoreland deserves the lion’s share of the blame.
He had full autonomy in prosecuting the war, and chose tactics that played well into enemy hands. He tried to kill as many of the enemy as possible, which really only strengthened their cause and turned every single person in the country against him. Search and destroy missions netted body counts that were exaggerated, not necessary or really justifiable, and often included civilians.
Poor decisions aside Westmoreland also lied many times to the American people, claiming that the situation was better than the actual reality. Just two months prior to the Tet Offensive in January 1968 – which turned the tide of the war against the Americans – he said, “We have reached an important point where the end begins to come into view.”
If that were true, then the NVA shouldn’t have been able to coordinate a massive assault on all US positions in entirety of the country, but if he had been talking about North Vietnam taking over South Vietnam then he would’ve been absolutely right.
Japanese Empire Admiral Kurita Takeo
There are a few Japanese Admirals that could have made this list (such as Vice Admiral Chuichi Nagumo who may have cost Japan the war by calling off an all important third wave of attacks on Pearl Harbor), but we’re going to focus on Admiral Kurita and his unsuccessful attack on Leyte Gulf in the Philippines.
This was arguably the largest naval engagement in the history of warfare, and after successfully fooling American commanders with a diversion (more on that in a second), he had a smaller US force dead to rights and in a vulnerable position on foreign waters.
Battle off Samar
Some extreme heroism from the American contingent called Taffy 3 deserves some praise here, but Kurita had an advantage in the battle that he failed to press home. He even had the largest battleship the world has ever seen (Yamato) at his disposal but turned it around before it could even fire a shot.
He didn’t think he was up against the small contingent of Taffy 3, which contained smaller escort aircraft carriers that he mistook for larger ones. Instead of crushing the small force protecting the American landing site in Leyt he lost four carriers, three battleships, and over 10,000 men.
United States Admiral William “Bull” Halsey
While we go through this list, it must be remembered that these men are here because of the terrible situation they created for the men who served them. General Sun Tzu (author of The Art of War) said to never put the burden of victory on your soldiers, but that’s exactly what Admiral Halsey did.
He did have a number of successes in WWII, but his over eagerness to win the war (he said he was going to ride the Emperor’s Horse when the war was over, a claim he never made good on) cost many lives in the Battle of Leyte Gulf.
Battle of Leyte Gulf
Prior to the first shots being fired in the Battle of Leyte Gulf, Admiral Kurita created a diversion that Halsey chased like a dog after a tennis ball. After taking the bait and chasing after Kurita’s carrier group, he left Leyte Gulf defended by only a small task force.
The move, dubiously known as “Hulsey’s blunder,” cost many sailors their lives. Making matters worse, Hulsey only turned around to help them when a damning message from his superior, Admiral Nimitz, arrived. The icing on the cake was that he subsequently threw a hissy fit and his subordinates had to calm him down.
French General Charles de Gaulle
I know some French people out there will not like this addition, but when you look at De Gaulle’s war record with an objective eye, it’s not very flattering. Of course, any French general in this time may have similar accolades, or lack thereof.
The French banked the fate of their country on a set of fixed fortifications called the Maginot Line, which the Germans happily drove around and bypassed completely. De Gaulle was part of efforts to counterattack against Germany’s “blitzkrieg,” and while his actions were no doubt brave at a desperate time, his army was hammered in the process.
Dien Bien Phu
France then lost control of their country in just a few weeks. In exile he did successfully guide French resistance, which was a factor in the liberation of France. Years later, he would commit another serious blunder as part of French senior leadership’s decision to drop paratroopers into Indochina (Cambodia, Laos, and Vietnam).
The hope was that France could hold onto their colonial possessions in the area after the war. That led to a separate seven-year war that ended with the French disaster at Dien Bien Phu, where all 15,000 men were either killed wounded or captured. Then in 1956, France also lost possession of Morocco and Tunisia in another ill fated war.
French Admiral Pierre-Charles-Jean-Baptiste-Silvestre de Villeneuve
While we’re picking on France, there’s an offender that probably did more to hurt French prestige than any other commander. The man with six names is the reason behind hundreds of years of British dominance of the sea. Napoleon (the actual Napoleon, not some impostor) gave orders to Villeneuve to draw the British fleet away from the British Isles, and then sneak back to support an invasion of the island nation.
Instead, Villeneuve drove straight at the British fleet, and his counterpart in Admiral Nelson promptly destroyed 19 of his 33 ships, without losing a single vessel of his own. As a result, the British were captains of the world’s seas for well over 100 years. As for Villeneuve, he was captured and later released, but decided to take his own life rather than face Napoleon.
British General Arthur Percival
England as a nation has over a thousand years of history, and General Percival has the distinct honor of being in command of the country’s most embarrassing defeat. Percival was well supplied and had a garrison of 100,000 men to defend his stronghold in Singapore during WWII. But when a force of 20,000 Japanese troops hacked their way through the Malay jungle and arrived behind the garrison, panic set in among the troops.
Unaware that he possessed an extreme advantage in numbers, and the Japanese were down to their last bit of ammunition, he was brow beaten into surrendering his 80,000 surviving troops. As Winston Churchill put it, it was the “worst disaster and largest capitulation in British history.” Percival should’ve fought it out, because 40,000 of the troops that surrendered died as POW’s to the Japanese empire.
United States General William Hull
Just like Percival, General Hull is guilty of surrendering to an inferior force with a ready army at his disposal. But Canadians probably will like him for that fact that he’s also one of the reasons Canada never became part of the United States.
Hull was given the task of defending Michigan from the British and attacking them in Canada during the War of 1812. In fairness, he was up against some very talented commanders, but instead of taking the fight to the enemy as he was instructed, it was the British who struck first when they took control of the Straits of Mackinac.
His response was to order the evacuation of a nearby fort (who were promptly slaughtered by a waiting band of Potawatomi warriors), and when he tried to regain the initiative his attack failed. His enemy pressed their advantage and attacked his headquarters at Fort Detroit. He then fell for a rouse put on by the British, when they marched their army around in circles to make it look like the force was much bigger.
Miss assessing the situation, Hull though he was outnumbered, so he quickly quickly surrendered the fort without firing a shot. Hull was captured and later returned to the US only to face a court martial for cowardice and neglect of duty. Ouch.
Tsar Nicholas Romanov II
Our list contains one last leader of a country who couldn’t shake his ability to constantly blunder. The tale of the last Tsar of Russia is a bloody tragedy that ends with him losing his life and his family would also pay the ultimate price for his mistakes.
But that’ll happen when you fight two wars over 20 years, never win a battle, and lose close to three million of your country’s people. Needless to say, his popularity within his country was damaged. In 1904 he emboldened the Japanese empire when his army lost the first major battle to an Asian nation in decades. This loss was the beginning of the end for the Romanov family.
Ten years later, he ordered his ill-equipped and under-trained army into early action against Germany in the early days of WWI. At the Battle of the Tannenberg, the Russian forces outnumbered German forces more than 2–1. Still, just about all of Nicholas’s force of half a million were either killed, wounded, or captured.
The Russian army lost a staggering four million men in the first year of the Great War alone. Unable to achieve success on the battlefield, and with general strikes and rising political tensions on the home front, just like Sadaam and Hitler did, Nicholas II lost his country.
United States General John Sedgwick
Okay, this next general certainly had more admirable qualities than anyone else on this list, but he arrives here for terribly underestimating Confederate rifle fire. General Sedgwick received the dubious distinction of being the most highly ranked Union soldier to be killed during the American Civil War, and General Ulysses S. Grant would say losing him was “greater than the loss of a whole division of troops.”
One of the reasons the Civil War was so deadly were the combination of Napoleonic tactics (there he is again!) and modern-day rifle technology. Lines of men marched to the slaughter as rows of bullets cut them down at distances of 500 yards. Upon seeing some of his men taking cover from long range rifle fire his last words before he was shot in the face will live in infamy: “Stand up. They couldn’t shoot an elephant from this distance.”
United States General Lloyd Fredendall
Probably the most embarrassing defeat for the United States in WWII was the debacle at Kasserine Pass, and the blame for that blunder lies squarely at the feet of General Frenendall. Untested in battle and fresh off the landing boat, General Fredendall was abruptly confronted by none other than famed and skilled German General Erwin Rommel.
“The Desert Fox” hit Lloyd’s men hard at the Pass, and Fredendall was well in the rear. His conduct during the fight would cost him his job (which was good, because he was replaced by General George Patton, who is not on this list for a reason).
Pass was known for cryptic messages that no one could understand. And while he was speaking babble to his troops, the enemy was gaining ground on their victory. This is why you always hear that communication is key and unfortunately for Pass, the stakes were higher thank usual.
His orders to his troops were as follows: “Move your command, i. e., the walking boys, pop guns, Baker’s outfit and the outfit which is the reverse of Baker’s outfit and the big fellows to M, which is due north of where you are now, as soon as possible. Have your boss report to the French gentleman whose name begins with J at a place which begins with D which is five grid squares to the left of M.” Um… What?!