Biggest "You Blew it!" moments in History (Pre-1900)

"You had it all and you blew it!"
What were the biggest "You blew it" moments in history prior to 1900?
Great Northern War: Sweden tossed away its mighty empire in a bungled war against Russia.
Battle of Karansebes: Worst friendly fire incident ever
Commodus in general
Khrwazm vs. Mongol Armies
 
Darius III cowardly fleeing the field at Gaugamela just as Mazaeus was about to break Parmenion's left flank. If he had a little more courage, Alexander would've failed. Also, Thomas failing to launch a sortie from Damascus just as Khalid was dealing with a relief force.
 
Bragg Post Chickamauga, full stop. He won the only real big victory in the west for the Rebels, and then he wasted it on political infighting with his subordinates.
 

Ficboy

Banned
Fredericksburg? (American Civil War). A Union force lost to much smaller Confederate Army due to tactical blunder?
The Maryland and Kentucky Campaigns. Coupled with Britain and France considering foreign recognition and intervention, it was the best-case scenario for the Confederacy to achieve independence and victory.
 
Would Battle of Adrianople count? Fell into an obvious trap and doomed the Western Roman Empire...
On non-military matters: Selling Alaska?
 
Antiochus III at Magnesia
The Western Confederacy when they decided not to press their advantage after the Battle of the Wabash to negotiate a favorable peace with the US
 
Charles IV & Ferdinand VII going to meet Napoleon only to both be deposed and lead to the collapse of the Spanish Empire (shoulda pulled a Portugal and ran to the colonies)
France through most of the HYW; Hapsburg Spain's entire existence
yeah absolutely. Spain kinda has a history of blowing things
 
Charles IV & Ferdinand VII going to meet Napoleon only to both be deposed and lead to the collapse of the Spanish Empire (shoulda pulled a Portugal and ran to the colonies)

yeah absolutely. Spain kinda has a history of blowing things
Honestly backing Napoleon made sense when Spain tried, since he was so dominant over Europe, but yeah that's a case of neutrality being the only option
 
Hmm.
Classic you blew it
Napoleon vs. Russia
Would it have been smarter to fortify his Empire's border with Russia and let the Russians come to him instead? That way the Russian Armies can't scorched earth or use their harsh climate as effectively.
 
Túpac Amaru II disregarding his wife's advice and not attacking Cusco when said city was completely vulnerable to his rebel army. By the time he finally decided to do so, it was too late and the rebellion was defeated.

Had Cusco fallen, Spain's colonial empire would've likely crumbled decades earlier than OTL, in the middle of the American and French revolutions.
 
The Makkan chiefs not looking in that particular cave while pursuing Muhammad(SAW), and his companions while they were on the Hijra. Though if you are a Muslim, maybe there was a divine element to it...
 
Sulla not putting Julius Caesar to death when he had the chance?

Richard III trusting Lord Stanley @ Bosworth Field?

The British Parliment refusing to accept Pitt the Elder’s plan to end the friction with the American
colonies.

(Post-1900): Wilhelm II issuing that “blank check” to Austria Hungary in the summer of 1914.
 
Last edited:
Would Battle of Adrianople count? Fell into an obvious trap and doomed the Western Roman Empire...
On non-military matters: Selling Alaska?
According to Louis L'Amour the Russians thought the British would seize Alaska if they didn't sell it, and by selling to America they got a buffer against the British Empire.
 
Top