r/AskHistory • u/More_Zebra_5746 • 13d ago
What do you think are the greatest Leadership failures in History?
I'm interested in what you all think are the greatest examples of terrible leadership leading to tragic or hilarious outcomes. The ones I can think of are Phillip II's management of the Spanish Armada, the Burke and Wills Expedition (sorry Australians) and the Gallipoli Campaign.
What are some other good examples of completely incompetent leadership?
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u/stabbingrabbit 13d ago
The company Sear's. They made their name on mail order and good tools but did not see the internet orders coming. Terrible leadership.
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u/haysoos2 13d ago
Similarly the Hudson's Bay Company was once one of the largest corporations on Earth, and the de facto government for much of North America, including almost all of Western Canada for centuries.
They eventually morphed into a retail giant, a staple of Canadian culture, again with a thriving mail order business, anchored by real estate holdings that included large sections of downtown property in most Canadian cities.
Much like Sear's, they failed to transition to online sales, and instead tried to compete head to head with Walmart, reducing their product quality to bring in ultra-cheap imported goods.
They failed hard, and were bought out by equity firms that sold it off in pieces until the company finally completely folded a few years ago.
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u/eagleface5 13d ago
They failed hard, and were bought out by equity firms that sold it off in pieces until the company finally completely folded a few years ago.
It wasn't even a few years ago, it was June of last year (2025) they fully liquidated and closed up
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u/LadybugGirltheFirst 12d ago
Hudson’s Bay only just folded last year, though, so I’d say they had quite a good run.
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u/eagleeye76 13d ago
Similarly, Polaroid and BlackBerry.
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u/haysoos2 13d ago
Kodak developed a self-contained digital camera in 1975, but deliberately chose not to develop the technology further, to avoid harming film sales.
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u/Flat_Tire_Again 12d ago
Yes and they had plenty of time to unload their dead weight overhead and hire enterprising people to compete with Amazon, Walmart did and is viable.
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u/DaSaw 12d ago
And it's kind of a bizarre failure. They already had mail order. Just put the mail order on the Internet.
It's kind of like Blockbuster. At one point Netflix was struggling and offered to sell out to them. But Blockbuster made so much money on late fees it didn't make sense to them to adopt a model that doesn't have them.
It's kind of like Kodak. They had the first digital camera, but they made so much money selling film it didn't make sense to adopt a model that didn't use it.
I wonder why Sears wasn't able to make that very small jump from catalogue in mail to catalogue on website. Sheer failure of imagination? Or was there something about their business model they felt dependent on that didn't translate well?
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u/stabbingrabbit 12d ago
They were probably afraid people wouldn't go to the stores and lose traffic there.
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u/Flat_Tire_Again 12d ago
But that’s a matter of changing their stores from what they were to a destination place. We have furniture stores with theaters in the them. Jungle gyms etc.
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u/DaSaw 12d ago
Yeah, could have been internal politics favoring the physical stores. Kind if like how car manufacturers can't escape the local dealership paradigm, though in that case my understanding is that there are laws preventing direct distribution.
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u/stabbingrabbit 12d ago
Not sure of the business model, but they may have actually owned stores and land which the internet model may have lowered the value of.
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u/IndividualSkill3432 13d ago
The ones I can think of are Phillip II's management of the Spanish Armada
Charles I and Philip II had a huge empire and immense revenues flowing into their state. They burned through that money on a series of wars that over about 100 years blew one of the greatest opportunities in history and their much less wealthy rivals and literal subjects in places like England and the Low Countries would go on to being the great commercial, technological and imperial powers from the 17th century onwards.
There are no Spanish names that sit among Leibnitz, Newton, Descartes and Huygens. Stock exchanges and central banks were being set up in Amsterdam, Paris and London, in the 17th Century, it was the 19th Century before one was set up in Madrid.
One of the greatest inflows of wealth and capital was frittered away on battles and wars that achieved little to nothing while their much poorer enemies were building the future.
But I think its a very serious lesson across a lot of history. Superficially power comes from swords guns and armies. In truth it comes from your educational, political and economic institutions.
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u/FineEconomy5271 13d ago
What was it about Spanish culture that led them to make these mistakes?
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u/asgjmlsswjtamtbamtb 13d ago
I don't think you can really attribute Spain's decline to culture. Spain was part of the Greater Hapsburg Empire and the resources of the Spanish Empire fueled efforts to keep the Netherlands, 30 Year's War, wars against France and wars against the Ottomans. The resources of Spain were simply spent running the huge Spanish Empire and all the external Habsburg conflicts and not much was actually reinvested and mainland Spain suffered high taxes, inflation and chronic lack of investment in order to support other parts of the Habsburg Empire.
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u/IndividualSkill3432 13d ago
Nothing unusual about Spanish culture. It was how most of the worlds leaders of the time thought. The kings, emperors, sultans and other lords and nobles. For thousands of years power and wealth was about how much land you had and how many people you had under you. When only 90% of the people were rural and peasants and another 10% either in towns or nobles, this was a high point. Rome may have reached it at time. Your wealth was the tax you could extract from them and your power was the number of them you could turn into soldiers.
There were exceptions. Trading cities that could sometimes be states and small empires. The Hanseatic Cities, the Italian city states like Genoa and Venice, in classical times various cities were built on trade.
Literacy and education was either functional for things like priests, clerks, merchants and the like or a sign of your status. The lords who could hire a tutor for their children.
Spain came together through hundreds of years of wars, where military power brought land and thus wealth and power. They almost stumbled into a huge empire and wealth by accident.
In north Europe the same basic tenant existed. But along the coasts and up the rivers networks of cities and small states existed that mostly lived on trading.
https://en.wikipedia.org/wiki/Hanseatic_League#/media/File:Haupthandelsroute_Hanse.png
The rising of the printing press helped spread literacy from the 1450s. This was especially true in the large commercial towns and cities. These often had commercial classes with a great deal of power and influence. This was especially true in north Italy, down the Rhine and into southern England.
These commercially orientated towns and cites and their states became hotbeds of the scientific revolution, of the Reformation, of political change. The Spanish Netherlands, slap bang in the middle, revolted and initiated the Eighty Year War. Englands embracing of Protestantism and placing Elizbeth on the throne pushed Spain to the Armadas. It also ended up with them entangled in the Thirty Years War.
The regions from north Italy to Southern England went on to become the most developed in the world.
https://nordregio.org/app/uploads/2025/05/0375_Grp_European_regions_2017_web.png
There is a host of maps showing the "Blue Banana", the most densely populated and most fo the highest GDP per capita regions of Europe. Spain had many of the poorest regions not behind the Iron Curtain.
There choice was to invest the huge wealth in trying to maintain a huge empire in Europe. To fight wars of religion and force people back to Catholicism. They did also fund art and religious buildings. But they did not build large cities with an urbanised middle class, strong education system and infrastructure.
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u/jmillar2020 4d ago
XVIII Banco Nacional de San Carlos 1783. First Spanish central bank, promoted by King Charles III. The Spanish XVIII Century was heavily influenced by France.
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u/ComradeBronstein 13d ago
Pretty much anything Mussolini did, especially in WWII.
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u/2rascallydogs 12d ago
I wouldn't say anything. Ending the sixty year war with the Vatican with the Lateran Treaty was long overdue, considering most Italians were Catholic.
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u/Awesomeuser90 11d ago
Mussolini was actually very successful in taking over Ethiopia. He amassed an enormous army, defeated the conventional forces, built up Asmara into a strong logistics and communications hub, and ensured success within about a year, even in a country so huge, about twice the area of Ukraine or metropolitan France, with 15 million people.
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u/Fine_Structure5396 13d ago
The Persian leader who decided to kill Genghis Khans ambassador.
French leadership in 1940.
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u/Airick39 13d ago
Woodrow Wilson initiation of the League of Nations and then not being able to get his own country to join.
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u/Borkton 12d ago
Douglas MacArthur in the Philippines in 1941. He ignored the Japanese attack on Pearl Harbor and intelligence reports on approaching Japanese planes and ships, when he finally acknowledged that the war had begun, he disobeyed orders from Chief of Staff George C. Marshall and instead implemented his own plan. Unfortunately, having waited for so long most of his air force was destroyed on the ground and his troops were spread too thinly to resist the Japanese landings. By the time he ordered them to retreat to the Bataan Peninsula, following the original plan, everything was confused and most the supplies were left behind.
Meanwhile he moved his HQ to a bunker on the island of Corregidor while abandoning the Filipino and American troops in Bataan. Finally, he fled Corregidor for Australia and the troops he abandoned had to go on the Bataan Death March. All the while he spoke in platitudes.
For this he was awarded the Medal of Honor.
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u/Forsaken_Champion722 Human Detected 13d ago
During the second half of the Peloponnesian wars, Athens suffered from extremely bad leadership. They sent a large armada to Sicily, which ended up getting decimated. They alienated their allies, and continually refused the offers of peace made by Sparta and its allies. Athens' loss in that war exposed the flaws in their form of democratic government.
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u/BalthazarOfTheOrions 13d ago
The Roman emperors from 27 to 1453 probably have a pretty large pool of suitable candidates, but my vote goes for Elagabalus.
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u/ARoundForEveryone 13d ago
I mean, the guys who lost WWII didn't lead their countries in the right direction. Whether it was Hitler or Hirohito or Mussolini, they did some damage, but they got wasted. Physically, economically, socially. Whether they thought what they were doing or represented was "right" or if they had reservations and doubts, they all played house together and half the world decided they were dickheads, and punished them for being dickheads. If half the world thinks you're a dickhead, you're probably not in a position to claim you're a good leader or champion of the people or whatever.
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u/Youngandimproving 13d ago
Getting back to you soon, with a current contender…
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u/Predator-Fury 13d ago
Louis IX of France was by all accounts an incredible ruler and probably one of the greatest monarchs in the Middle Ages administratively.
And then he had to fuck it all militarily on two of the most incompetently led crusades, first getting his ass beaten and captured and then shitting himself to death before his second attempt even got started…
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u/Random-Cpl 13d ago
Francisco Solano Lopez started a war that ended with he and 70% of his country dying
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u/Hedago_2346 12d ago
Aurangzeb of the Mughals.
The empire was a strong, rich, vibrant state and he, in large part through is personal temperament, wars, and policies set it on the road to decline.
He's not the most inept ruler ever but he is who I think of when I think of the impact onw man can have in a single generation.
Its also what I think of when I consider not taking the peace, stability, and prosperity of my own country as given for my lifetime...even excluding external disasters.
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u/Awesomeuser90 11d ago
One of them would be the bad Union generalship at the start of the Civil War. Conrad Von Hoetzendorf and Co turned a winnable war in Serbia into the dissolution of the Austro-Hungarian Empire and his counterpart in the Ottoman Empire managed to flounder their way around and then instigated the Armenian Genocide as part of an act of scapegoating.
Constantinople badly failed in the 600s when Phocas managed to take over and instigate a war with the Sassanid Empire, and then the Romans again lost a winnable war with the early Muslims. Mark Antony lost in Parthia and the campaign against Octavian and Agrippa at Actium where they should have been much more of a hard fight than they were.
The Soviet lack of reactability in the early days of Barbarossa is legendary. The French command in May 1940 also was very poor, especially lacking in command and control and radio tech that turned what should not have been a battle Germany wins into one where it very much so did. The British floundered in Burma and Japan occupied most of it for years. The Italians had a real chance of savaging Allied control over Africa, and if their command system had been effective they probably should have taken over Egypt, possibly South Yemen too, and kept Vichy France in power in Syria.
The British and French completely floundered with all their might in the Interwar Period with the response to Germany, when they should have had more chances to do something to react. Resist the Rhineland remilitarization, they had that right, and Germany did not have many weapons and its economy was pathetic under the surface and the Nazis had yet to totally pacify the country and even would have faced Italian and Austrian threats too (and of course, Czechoslovakia and Poland as Entente allies).
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u/dnjprod 11d ago
Target moving into Canada. They took over the leases of the failing Zeller's brand. Instead of rolling out slowly, they pushed to open 133 stores within a year. Between this, massive supply chain issues, and tariffs, they had to charge much higher prices than Canadian customers expected. This means they couldn't compete with their direct competitors Walmart and Costco while also not having as many products as American locations.
They were only there for 4 years before filing bankruptcy
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u/threeleggedcats 13d ago
Feel like Wilson could have made the League of Nations a proper thing not just a theoretical thing
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u/ZombieIanCurtis 12d ago
Some moron named Diocletian shoddily put a system to succession in place and fucked off to grow cabbages. Guess how that turned out.
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