What would y'all say are some of the most profound "yikes" moments in history. Moments where a leader/commander realized they'd miscalculated badly. Custer at Little Bighorn comes to mind. Give me some other classic ones!

Varro and Paullus allowing their water supply to be cut off and then marching their legions directly into the middle of a Carthaginian trap at Cannae.

Battle of Hattin. Crusader forces marching out into the parched desert with no water supply where they were easily overwhelmed and destroyed by Saladin's army.

It's been mentioned but in Western history probably the two most well known examples of miscalculations leading to disaster are Napoleon's invasion of Russian and Germany's Operation Barbarossa/Case Blue. I'm not sure these really count as a single yikes moment or battle decision leading to disaster. They seem to count more as a systemic failure of the Military chain of command that places complete control at the very head of the Government.

I was just reading about the Visigoth sacks (plural) of Rome and… yikes. No reason for it to have gotten to that point. The Visigoth leadership wanted some land and some tribute. The Roman leadership was both duplicitous in the negotiations and made multiple attempts to form an army that never materialized. Finally the Visigoths had enough and reading over it, you can understand their actions.

The misadventures of admiral nagumo. (At pearl and midway)

The US decision to invade Canada in 1812 was an astounding miscalculation and blunder. Possibly the worst blunder in American history if you think about it. Not only did the we completely miscalculate the Canadian desire to a part of the US, we also lacked the military leadership to carry out the invasion, Hull and Dearborn were wholly incompetent.

Gaius Terentius Varro at Cannae since legend says it was his day to command and he seemed more arrogant than Pallus.

The peace agreement that the Delawares (Lenape) made with the Iroquois (Mengwe) before the French and Indian War and its subsequent effects on North American history.

Sure Mr. Maginot, your plan of fortifications along the border sounds like a great buy!

I'd say the James Gang kind of had a "yikes" moment coming out of the bank at Northfield, Minnesota!!

The Army of Northern Virginia, on July 3, 1863, when they realized that the Union artillery supporting Hancock's II Corps in the center of the Union line hadn't been knocked out after all, but just holding their fire.

Soviets invading Finland in 1939 in the winter war.

Rabid Cougar said:

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Smeghead4761 said:

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The Army of Northern Virginia, on July 3, 1863, when they realized that the Union artillery supporting Hancock's II Corps in the center of the Union line hadn't been knocked out after all, but just holding their fire.

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And yet they still went in and broke the line….

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"Broke the line" is debatable. They were obliterated almost immediately by fewer than half the number of Union soldiers as Confederate.

Jaydoug said:

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Texas joining the United States

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A case can be made that Texas would have been better off if it had been able to keep its original borders. avoid the War Between the States (and join Britain and France in making slavery illegal), and keep ALL its oil & gas revenues....but the reality was Texas was broke and very threatened.

Cordova Rallies Indians in a War Against the Texians, Burleson Meets Him at Seguin, 1839 - YouTube

Edit to show a map of Federal posts that helped to protect the Texas frontier just BEFORE the Civil War.
See it at 7:20 of the following account of General Baylor vs Comanches...and know that without this protection the Indians pushed the frontier back many miles

General Baylor's Fight with Comanches on Paint Creek, 1860, Parker and Stephens Counties - YouTube

Rice and sugar cane are both grown in low, wet, hot areas that Europeans didn't have the evolutionary background to stand as well as black Africans could, as a generality.
Cotton became a big crop later and could be grown in places like West Texas where cotton farming was done by anybody and everybody poor to have enough to have to do it.

doubledog said:

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Battle of the Somme

EOT.

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I've always thought this was one of the worst decisions ever made. Allied casualties exceeded 620,000 with 60,000 British dead or wounded on the first day.

Oh, and anyone who ever picked a fight with Genghis Khan.

I've always thought Tarleton must have had an impressive "yikes" moment at Cowpens when the militia he had just dispersed suddenly reappeared on his left flank.