10 Daring Bluffs That Paid Off Enormously

It’s inspiring to hear stories of people using hard work, intelligence, and charisma to assemble great and powerful forces to accomplish amazing things. But we’re not about that with this list. This is about people being sneaky or full of chutzpah to take on opponents in better positions. These stories have all the satisfaction of a good underdog story while also indulging a common suspicion that beyond appearances, a lot of things that seem all-powerful in reality aren’t. From huge military bodies, to powerful businesses, to expert athletes, people who can take advantage of someone else’s uncertainty can achieve what we only dream about.

10. John Dillinger Breaks Out of an “Escape Proof” Prison with a Wooden Gun Despite Dozens of Guards

In 1934, John Dillinger was the most famous bank robber in America, which gave him a certain folk hero status during the Great Depression due to the grudge the average American had with the banks that were evicting so many people from their homes with foreclosures. However, that same year he was imprisoned in Crown Point Prison in Indiana, an institution with so many guards and stop-gap doors that it had a reputation for being escape proof.

Undeterred, Dillinger carved himself a wooden Colt pistol (more like just a fake barrel: The prop didn’t have a full fake handle). With the fake gun and a system of locking every guard and prisoner in cells and offices as he went through, Dillinger bested thirty-three guards and left the prison with the sheriff’s car and two machine guns. He was dead within a year, but the story of that escape is a legend that will never die.

9. George Washington Drives the British from Boston with Nearly Empty Cannons

We mostly remember the fight for the city of Boston during the American Revolution for the Battle of Bunker Hill, and have overlooked the action that won the Americans the city. In 1775, the American army captured Fort Ticonderoga in New York and began the arduous task of moving its heavy artillery to Boston under the supervision of Henry Knox. In January 1776 the cannons arrived and George Washington very conspicuously placed them at the American stronghold of Dorchester Heights.

As it happened, for more than a month after the artillery arrived, Washington’s army wasn’t in a good position to fire them. Indeed the American army was so badly equipped and the infrastructure of the country was so impoverished that they barely had enough gunpowder for their troops, let alone for artillery bombardments. There had been a pretty strong indication of this when the Americans had been driven from Breed’s Hill because they had run out of ammunition. Yet the British commander William Howe was kept at bay by weapons that were essentially empty, and in March 1776 he negotiated terms of retreat with the Americans threatening him with cannons they could barely shoot. It was one of the greatest American victories of the war.

8. Siege of Yorktown

In March 1862, relatively early in the American Civil War, Union commander George McClellan had a clever solution to the problem of capturing the Confederate capital of Richmond, Virginia while a large Southern army was between it and his base in Washington, DC. He landed over 60,000 troops on the Virginia Peninsula, adjacent to Richmond, basically allowing him to approach the city from behind, where there were only about 10,000-13,000 Confederate troops.

The commander of the Confederate army was James Magruder, and he more than made up for the disparity in numbers with guile. He mislead his opponent by having large parts of his command march in circles in areas observable by the Union. To reinforce the ruse (and possibly disturb his enemy’s sleep) he had his bands play music for more fictional arriving troops at night. In the end, McClellan overestimated his enemy’s strength ten times over, leaving him hesitant to attack. It allowed the main Southern army to move south and eventually stop his army at the Battle of Seven Days, leaving the whole campaign a drawn out failure.

But McClellan was not done being on the receiving end of very audacious bluffs.

7. Battle of Antietam: Stand with Cartridges

Best known for being the single bloodiest day of American military history, the signing of the Emancipation Proclamation, and on Toptenz for being the battle where one of the stupidest blunders ever occurred. But it also featured an absurdly, impressively awesome bluff on September 17, 1862. The battle had begun with an attack on the Confederate Army’s western flank. By 9 a.m., the Union troops under McClellan shifted their attacks to the Confederate center at a place called Sunken Road, where so many soldiers from both sides were killed that it became known as Bloody Lane. By noon, the Union troops drove the Confederates from their positions, meaning the Confederate Army was on the verge of collapse.

As the Union paused to consolidate their positions, a scant force of Confederates rallied and stood, daring the enemy to attack them again while a few artillery pieces fired on the Union troops on the edge of victory. The Confederates weren’t just tired and hopelessly outnumbered (during the entire battle they would be outnumbered more than two to one). They were also so short on ammunition that their commander General James Longstreet said of them “They haven’t a cartridge.” Longstreet would also say that if McClellan sent as few as half of the troops he was holding in reserve into the battle, he would have completely destroyed the Southern Army. Instead, once again, McClellan pulled back and basically let the Confederates get away.

Considering that their army not being destroyed at that battle resulted in the deaths of hundreds of thousands of Americans, the eventual passing of the 13th Amendment, and the burning of multiple Southern cities, even the Confederates probably eventually wished they’d just let McClellan win.

6. Battle of Fishguard

In 1797, France was expanding into the powerhouse on the world stage it would become under Napoleon Bonaparte. This venture was one of its more awkward moments as well as the last time in modern history that the United Kingdom was invaded by land. In February the French landed about 1,400 soldiers near Llanwnda in Wales. The landing site was chosen under the assumption that the Welsh were as inclined to rebel against British rule as the Irish. Even if that were the case, the fact the French soldiers’ first act was to raid a local community was not the wisest way to inspire enthusiasm.

The British could muster an army of only 600 to first meet the French invasion under the command of Colonel William Tate. However, thousands of other Welsh civilians came near the site of the two small armies. Not to enlist in the defense, or any such thing. They just wanted to see the fight. However, as many of them wore traditional red clothing, Tate was able to claim to the French that the ranks of civilians were hastily recruited soldiers and negotiate the surrender of the much larger French force without a fight. Rarely have mobs of bystanders been so useful in war.

5. Rhineland Militarization

When they think of the period leading up to World War II, most people picture Neville Chamberlain making concessions to Adolf Hitler and the Third Reich in the pursuit of “Peace in Our Time.” However, in 1936 one of the greatest opportunities to improve the 20th Century was passed up. In March of that year, Hitler ordered 16 battalions (about 22,000 troops) into the Rhineland in Western Germany, a move explicitly prohibited in the Versailles Treaty, which had ended World War I.

To counter this, the French had an army of 100 divisions available, numbering in the hundreds of thousands. As mad and stupid as Hitler was, he knew well enough that if the French so much as crossed the border, he would have to order withdrawals. However, memories of WWI were too fresh and invading the Rhineland was judged too expensive, so the violation stood, emboldening the country to plunge Europe into war.

4. Ferdinand Demara

Let’s take a break from the military entries and focus on a man whose story was as inspirational as it was eccentric. Ferdinand Demara was a man who lived from 1921 to 1982 and spent many of those years bluffing his way into assuming other people’s identities. From 1941 on he would take jobs in the American Armed Forces under the name of his friend Anthony Ignola, then eventually desert and become a monk in Louisville, Kentucky. He then went west and took the identity of Dr. Cecil Harmann to study law. While continuing to convince people of that stolen identity, he met a doctor named Joseph Cyr, and decided to bluff his way into being Joseph Cyr as he enlisted in the Canadian Navy in time to serve during the Korean War.

He was able to continue convincing people of his false identity, and wound up performing some pretty astounding, and very real heroics: during his time in the Navy, the untrained Demara performed 16 lifesaving surgeries, including bullet extractions. It was an amazing feat that blew Demara’s cover, since his surgical feats as Joseph Cyr got him featured in Canadian news, prompting Cyr’s mother to protest that someone in the Navy was posing as her son. It was not Demara’s last feat under an assumed identity, but it was such a great trick pulled on the world that in 1961 a film was made about him called The Great Imposter, in which Tony Curtis assumed Demara’s identity.

3. Pakistan’s Flight 544

On May 25, 1998, three hijackers took this airliner with thirty-eight people aboard hostage. They demanded to be taken to India even as the hijacking drew jet interceptors. Thinking quickly, the pilot claimed that they didn’t have the fuel to fly to New Delhi, the city the hijackers had in mind, and offered instead Bhuj, much closer to the border with Pakistan. In fact, he was flying to Hyderabad, where Pakistani police were waiting.

The pilot spoke to the airport tower in Hindi to reinforce the illusion that they were in thoroughly Indian territory, and on the ground all lights that illuminated signs that it was Hyderabad were turned off. The pilot continued speaking Hindi as police, claiming to be bringing supplies and fuel, surrounded the plane. Everyone he communicated with continued the ruse until they were in place to overpower the hijackers. The passengers were saved without a life being lost. As for the hijackers, they were executed by hanging 17 years later.

2. Maskirovka

The Nazis had no monopoly on using bold power plays without the material strength to back them up during the Second World War and the buildup. One of the most significant and overlooked instances of this was performed by the Soviet Union in 1942. In the lead up to the portion of the Battle of Stalingrad where the Soviets attacked from the north and south to surround the German 6th Army that was stuck in there, the Soviets began bluffing pretty much everywhere other than the areas they intended to attack.

Defenses around Moscow were built up, and radio activity increased in those areas. Most ambitious of all was the construction of 17 phony bridges to lead the German air force to believe that the Soviets were planning to cross bridges to attack areas other than their real objective for encirclement. The effort was so successful that the German Intelligence completely fell for it, leaving the areas around Stalingrad vulnerable enough for the Soviets to win perhaps the most significant victory of the war.

1. Nguyen’s Win

Let’s finish this list with an example of the kind of bluff the average reader is most likely to engage in: Bluffing at a game of poker. The single most successful bluff in poker history was performed by Qui Nguyen against Gordon Vayo in November 2016. From the beginning Vayo had the advantage, and initially thought that he was the one luring Nguyen by betting $9.7 million, which Nguyen accepted. Then when the second card was put into the river, Nguyen moved into bluffing mode, greatly increasing the bet even though Vayo had a 90% chance of winning.

When the final card was uncovered and Vayo had a hundred percent chance, Nguyen went all in. After thinking about it for minutes, Vayo decided to fold. Nguyen won $162 million in chips and a total of $8 million for his incredible nerve with a lousy hand. Surely Gordon Vayo will never fold again if anyone might ever be bluffing him… right?

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