11 Risky Military Moves That Actually Paid Off

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Vote up the moves that most justified the risk

The scrapheap of history is piled high with risks that didn't pan out. As one WWII general wryly observed, the first rule of war is that you don't march on Moscow. History has turned on those ill-considered decisions, but every so often, risky moves actually work out. 

Many of the most accomplished military commanders in history achieved some of their finest victories on the back of great risks. From Alexander the Great's devil-may-care approach to battle to Ulysses S. Grant's uncomplicated personal art of war, this collection looks at those risky military moves that fortunately paid off.

  • Napoleon's Greatest Victory Was Still A Major Gamble
    Photo: United States Military Academy / Wikimedia Commons / Public domain

    Napoleon fought 60 battles over the course of his career, and possibly the greatest of his many victories was the triumph at Austerlitz, in what is now the Czech Republic. He smashed a combined Austrian and Russian army, ending the Third Coalition and cementing France’s position as the dominant force in Europe at the time. 

    During the conflict, Napoleon sought to bait the larger Austrian and Russian armies into a decisive engagement by appearing much weaker than he really was. It’s unlikely he ever had a chance to flip through Sun Tzu’s The Art of War, but his plans perfectly encapsulated the ancient text’s advice for fighting on favorable terms:

    Hold out baits to entice the enemy. Feign disorder, and crush him.

    Napoleon feigned a retreat to Austerlitz while sending out envoys to seek a settled peace, a trick to persuade the allied army to press their apparent advantage and attack his much smaller army. Unbeknownst to Russian Czar Alexander I and Holy Roman Emperor Francis II, Napoleon had reserves close enough to join the battle he was trying to force.

    Even with his hidden reserves, the French army was still well outnumbered and faced an enemy in a strong defensive position. To entice the enemy out, Napoleon left his southern flank under General Claude Juste Alexandre Legrand weak. Reinforcements from Vienna set out to relieve Legrand once the battle was joined, but any delay would be fatal. The plan was incredibly risky and hinged on the ability of Legrand’s heavily outnumbered division to hold the line long enough for Napoleon’s battle plan to work.

    The Austro-Russian army took the bait and shifted to envelop the weak French flank. As they pivoted to overwhelm and the French right flank, Napoleon waited for the optimal moment to launch his main strike at the Austro-Russian center. The approach of the main attack was masked by mist, and had that lifted earlier, the ruse would have been foiled. But his luck held that day. As he ordered the attack of the 16,000 men under Marshal Nicolas Soult, Napoleon remarked:

    One sharp blow and the war is over.

    The attack smashed through the middle of the Austro-Hungarian army as planned. By the time the dust had settled, the Austro-Russian army was in tatters; 36,000 men were killed or captured. 

    It was a remarkable victory, but one that relied on gigantic risks paying off. Napoleon risked it all to win it all - for a while at least.

    52 votes
  • The Manstein Plan Was Only Tried Because Of A Plane Crash
    Photo: Bundesarchiv, Bild 183-H0175 / Wikimedia Commons / CC BY-SA 3.0 DE

    After the invasion of Poland, WWII was unusually quiet. German peace overtures were rejected as the Allies looked to confront the German army in the Low Countries. The often-maligned Maginot Line did its job, by funneling the Wehrmacht into the Netherlands and Belgium rather than invading France directly. The Allies essentially intended to redo WWI, but with fewer losses outside of France. Fighting on the defensive favored Britain and France. With overseas empires to draw upon, time was on their side. 

    The Germans needed to win - and quickly - so in the winter of 1939-40 they tried to come up with a war-winning offensive. The initial plans were quite similar to the Schlieffen Plan in WWI - an advance through the Low Countries to encircle Paris. The plan was unlikely to succeed in 1914 and was all but impossible in 1940. Erich von Manstein had another idea, a risky plan to move an armored column unexpectedly through the Ardennes Forest and punch through the Allied lines at Sedan. The German command was hesitant to adopt such an unorthodox approach, but when a plane carrying German plans crash-landed in Belgium, a new approach was required.

    Manstein’s plan worked better than the Germans dared to dream. The Allies were still thinking in WWI terms and allowed a tactical setback to escalate into a strategic disaster. After breaking through the Allied lines, German panzers raced to the coast, encircling almost the entirety of the British expeditionary force in the process. Only a swift evacuation at Dunkirk saved the British from certain defeat, but France was doomed. Often seen as the birth of Blitzkrieg, the Battle of France was a gamble that paid off spectacularly for the Germans. However, every subsequent attempt to repeat the success of 1940 ended in dismal failure.

    31 votes
  • The Mongols Broke The Rules Of War To Take Moscow
    Photo: Vassily Maximov / Wikimedia Commons / Public domain
    24 VOTES

    The Mongols Broke The Rules Of War To Take Moscow

    Rule 1, on page 1 of the book of war, is: “Do not march on Moscow”… [Rule 2] is: “Do not go fighting with your land armies in China.”

    WW2 General Bernard Montgomery’s knack for pithy quotes was only moderately overshadowed by his penchant for self-promotion. The two maxims outlined in a speech to the British House of Commons generally hold true, but not completely. In the 13th century, the Mongols launched a successful invasion of Kievan Rus, a medieval kingdom that incorporated parts of Russia, Belarus, and Ukraine. 

    Not only did the Mongols march on Moscow successfully, but they also did so in the midst of winter. It was an attack the Russian princes had brought upon themselves. Mongol emissaries sent into Kievan Rus were promptly slain by the princes who felt they couldn’t trust any deal struck with the Mongols. The Mongols came back in great numbers under the leadership of Batu and Subutai

    While the harsh winters of Kievan Rus might have stayed the hand of western armies, the Mongols were made of sterner stuff. The famously durable Mongol ponies and their equally stout riders traveled light to cover vast tracts of ground. The Mongol horde reached Moscow in January 1238 and sacked the city after just five days. Moscow would come under Mongol dominion until the 16th century, and Kievan Rus effectively ceased to be. The invasion had a huge long-term impact on the history of Russia.

    24 votes
  • General Grant Took Huge Risks During The Vicksburg Campaign
    Photo: Currier and Ives / Wikimedia Commons / Public domain

    In 1862, an ambitious combined operation to seize the Confederate capital of Richmond, VA, fell flat when the Union army led by George B McClellan hesitated and allowed Robert E. Lee’s forces to muster and launch a counteroffensive to drive the Union army out. 

    A year later, a similar operation was unfolding in the west to take the key stronghold of Vicksburg, MS. To seize the city was to wrest control of Mississippi and effectively cut the Confederacy in two. Unlike McClellan, Ulysses S. Grant had no qualms whatsoever about pressing an advantage. He once outlined his approach to combat in a characteristically unpretentious way to a surgeon

    The art of war is simple enough. Find out where your enemy is. Get at him as soon as you can. Strike him as hard as you can, and keep moving on.

    An earlier Union approach to Vicksburg had been foiled when Confederate cavalry cut supply lines. Rather than try to secure a long supply line, Grant used the Mississippi itself as a barrier. The gunboats under David Dixon Porter’s command ran through the gauntlet of coastal barriers at Vicksburg to make a crossing to the south of the city. The risky gambit worked as Porter's ships got through intact. Grant’s army made it across, but without a secure supply line. 

    The need to move quickly justified the enormous risk of outpacing his own supply line in Grant’s eyes. His subordinate generals were alarmed by the idea, but Grant believed his men could live off the land long enough for supplies to catch up. Where the Union army in the east made slow progress, Grant’s forces moved with breakneck speed to engage and defeat several smaller Confederate armies before they could meet up with the garrison at Vicksburg under John Pemberton. 

    Grant’s army managed to get in between Pemberton’s garrison and a relief army under Joseph E. Johnston. The speed of Grant’s army prevented the two forces from combining and presenting a credible threat to the Union army. The city fell after a 47-day siege.

    28 votes
  • Alexander The Great Risked His Life At The Granicus
    Photo: Charles Le Brun / Wikimedia Commons / Public domain
    26 VOTES

    Alexander The Great Risked His Life At The Granicus

    Alexander the Great is heralded as one of the greatest military commanders in history, and with good reason. His conquests over the course of 13 short years forever changed the world and cemented his place in history. Not bad for someone who didn’t see the age of 33.

    For all his great accomplishments, there’s little doubt Alexander made some incredibly risky moves throughout his career. His habit of leading from the front was certainly brave and inspiring, but it also meant his conquests relied heavily on luck. Few examples typified this quite like his first major battle against the Persian Empire at the Granicus. 

    His army found itself facing a satrap of Darius whose forces were bolstered by just over 5,000 Greek mercenaries led by seasoned commander Memnon of Rhodes waiting for them on the other side of the Granicus River. Had the Persians actually listened to the Greek commander, Alexander might have been undone long before the battle. 

    A contested river crossing is usually a major tactical faux pas, especially on horseback, but the rules of war don’t seem to apply to Alexander. He figured the Persians were relying on geography rather than courage, and so personally led a charge against the Persian cavalry on the opposite side of the river.

    Fortunately for Alexander, the Persians had rather obligingly placed their mounted forces in front of the Greek mercenaries, rendering Memnon’s troops little more than bystanders. Still, Alexander’s conquests almost came to a swift and ignoble end when he was very nearly slain by a Persian noble named Spithridates. Only the timely intervention of Clitus the Black saved Alexander’s skin. After a hard and dangerous skirmish, the Persian cavalry broke and Alexander’s whole army turned against the now badly outnumbered Greeks. Although quarter was sought by the mercenaries, it was not given. The few who lived were enslaved as Alexander's army marched onward.

    26 votes
  • Robert The Bruce Staked His Kingdom On Winning The Second Day At Bannockburn
    Photo: Andrei Nacu / Wikimedia Commons / Public domain

    The Battle of Bannockburn was a decisive engagement in the First Scottish War Of Independence with England. At the time, the only major Scottish stronghold in English hands was the key castle of Stirling, right in the heart of the kingdom. Because of its central location and proximity to Edinburgh and Glasgow, Stirling has been historically viewed as the key to Scotland.

    The English garrison commander agreed to surrender the castle if a relieving English army did not arrive in time. Edward II, the disappointing heir to Edward I, personally led a sizeable English force to save the castle. Robert the Bruce gathered his men to block the path to Stirling Castle at nearby Bannockburn. 

    Generally speaking, the Scots did not fare particularly well against the English in pitched battles. Superior English arms and deadly longbows meant most of the skirmishes went the way of the English, but the Scots were never out for very long. Robert had shown himself to be a very effective guerilla leader, but he knew that sooner or later he would have to defeat the English in battle to secure his crown. 

    On June 23, 1314, the Scottish army clashed with the vanguard of the English force. The Bruce even defeated an English knight in single combat. The carefully chosen ground greatly favored the Scottish pikemen as the mounted English knights failed to gain any ground. As the Scots retired to the woods at the end of the first day, Robert strongly considered quitting while he was ahead. As he pondered his fate, a defecting knight arrived to report that English morale was low and urge him to push his advantage. Robert chose to risk it all the following day.

    As they approached the English army they knelt. Edward II mistakenly took this as a plea for mercy, but an English knight reportedly said they were praying for mercy from God, not Edward:

    These men will either conquer or die.

    The second day was a brutal slog in the marshlands; the mounted knights made no headway while the English archers were kept at bay by Scots cavalry. As the English were pushed back to the banks of a nearby river, the Scottish camp followers - a motley rabble known as the “Small Folk” - appeared from the woods. The appearance of the Small Folk broke the English army’s will to fight on. Many drowned attempting to escape, and Edward II was very nearly taken prisoner as he fled. Only a handful of English troops made it back safely. The struggle for independence would continue, but the victory at Bannockburn was a pivotal moment in the struggle.

    22 votes