Top 10 Generals Who Switched Sides

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Can you imagine serving under a general who until recently was commanding soldiers who wanted to capture or kill you? Would you ever trust that person to be at all concerned for your safety or loyal to the cause at all? Well, thousands and thousands of soldiers have had to put up with that situation. It has worked out for all parties involved in many interesting ways, sometimes in very surprising ones.

10. Jean-Baptiste Bernadotte

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Napoleon’s relative by marriage to Josephine, he rose to the rank of Field Marshal (commander of about 20,000 men) and was with Napoleon through 1805 to 1809, winning numerous battles. However, in 1809, during the Battle of Wagram his corps was routed and Bernadotte rode back to try to rally them. Napoleon saw him doing that, mistook his actions for fleeing the fight, and ordered him to leave the battle. A few years later, Napoleon fired him after a couple more blunders including bragging about how many troops he had to the press. Naturally bitter, Bernadotte lucked out in a big way after his reputation and connections (even despite being the general Napoleon fired) got him the position of Prince of Sweden, and by 1813 the title commander of the Swedish Army.

When Napoleon invaded Russia, he offered to invade France if the Czar would give him Norway. The deal fell apart but after Napoleon’s disastrous campaign he finally took arms against his old Emperor, contributing to his defeat at the Battle of Leipzig, the largest and bloodiest battle of the Napoleonic wars. In 1814, he approached a French fort to receive its surrender, and when he was shot at despite having a flag of truce, the soldier said he’d merely been trying to apprehend a French deserter. While writing his memoirs, Napoleon generously said the general and eventual King of Sweden was not a treacherous man, just an ungrateful one.

9. Andrei Vlasov

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A Russian general who was so prominent in the defense of Moscow in 1941 that he was dubbed “The Hero of Moscow,” Vlasov’s changing allegiance seemed to have more to do with desperation than treachery. His number came up in when in 1942 he was in command of an attack to lift the siege of Leningrad and was captured when the entire attacking army was encircled. He defected while a prisoner and supposedly took command of the “Russian Liberation Army.” Since the Nazis weren’t about to trust the sorts of prisoners they would usually force into labor with guns, it was mostly a nominal position until 1944 due to the fact that the Nazis had become that desperate. The unit was about 50,000 people and saw combat once. Soon they attempted to surrender to the Americans in Czechoslovakia, seemingly the safest bet for mercy after the war. It turned out the Allies were in no mood to be merciful to traitors, and he was turned over to the Soviets, which effectively doomed him. It’s frankly a wonder it took until 1946 for him to be executed.

8. Alaric

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His main claim to fame was that in 410 he was the first Barbarian for centuries to sack Rome, signalling the end of the Roman Empire in the West. Prior to that, however, he had been a loyal and successful general for Rome, particularly at the battle of River Frigidus. However, his followers were betrayed by not being granted rights to the land they intended to settle on and formed an army to pressure Rome to pay up for that land in gold. His main opponent would have been Flavius Stilicho if it hadn’t been for a member of the Roman Olympius who suspected Stilicho troops were disloyal and ordered another group of Roman soldiers to put them and their loyal general to death. The most significant effect of this was that Alaric was easily able to add 30,000 of Flavius’s former soldiers to his defiant army, showing that treachery is often not the best way to combat perceived treachery.

7. Ashikaga Takauji

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Although there’s a stereotype in America that came out of caricaturing them in World War II that Japanese society is obsessed with honor and loyalty, feudal Japan is full of stories of generals who switched allegiances. Ashikaga Takauji from the fourteenth century has to be the most successful. In 1331, war broke out between the emperor of Japan and the Hojo Dynasty who were basically functionaries running the country. The emperor was defeated, but tried it again in 1333. This time the commander of the Hojo forces was Takauji, who decided to abandon his command, go home, and raise an army for the emperor. He succeeded in helping get the emperor on the throne, but two years later, the Hojos raised a new army. Takauji went and defeated them, and was rewarded with accusations he had murdered a prince during the campaign. Takauji switched sides again and drove the emperor out of power and had himself declared Shogun (i.e., dictator) of Japan, starting a bloodline that would last into the later half of the sixteenth century. Despite apparently being ready to fight with just about anyone on his way up the chain of command, it should be noted that he was supposed to be a kind, generous man of an artistic and religious nature in person.

6. Alcibiades

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Never has someone betrayed so many factions only to end up back where he started. In the fifth century BC, Alcibiades was a charming, hard-drinking, troublesome Athenian who was well-known to be unusually attractive. Although he had a good record, during one night of carousing he defaced statues of the god Mercury and had to abandon the city before he was sure to be punished after a show trial to appease the Gods. He offered his services to Athens’ sometimes rival, Sparta, and advised them on how to inflict some martial disasters on the Athenian military. Aiming high in terms of angering his new hosts, he impregnated the queen of Sparta and naturally soon had to flee. His new hosts were the Persians, whom he urged not to help the Spartans in their war with Athens before abandoning the Persians to seek a command with, of all places, the Athenians again, which he amazingly was given. He also was reunited with his old mutual admirer, the famous philosopher Socrates.

5. Bartolomeo Colleoni

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While we associate the Renaissance with great advances in art and philosophy, for the average person it was a frightening, war torn period, particularly in the constantly feuding nation states of Italy. Bartolomeo Colleoni was a mercenary who in 1431 joined the ranks defending Venice. By 1439, he was commanding 1,200 troops. By 1441 the war between Venice and Milan stopped temporarily. Apparently thinking that meant they could do what they wanted to their soldiers, the Venetians didn’t pay Colleoni the 32,000 ducats amount owed. Colleoni responded to that by joining Milan in 1442, and for four years fought against his old employers before being arrested on suspicion of conspiring to go back to Venice. After a year in prison, he was cleared of charges and appointed commander of all Milanese soldiers, where he then thoroughly beat French armies that had invaded.

In 1448, Colleoni was rehired by Venice (how either could have suspected the other party wouldn’t cheat them again is a mystery.) He fought against Milan again for two years before finally conquering it. But then, once more, Colleoni was almost going to be arrested to prevent him from leaving before his contract was up, so he went back to the apparently very understanding arms of Milan and fought against Venice again for two more years. In a truly bewildering final act, once more in secret he was rehired by Venice, and this time finished out his term in command of the Venetian army where he remained until he retired from his topsy-turvy military career.

4. Phanes

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Anyone who has seen 300 might be inclined to think Greece and Persia were the bitterest of enemies, but decades before the events of that film, a Greek general rendered a service vital to the Persian empire. In 523 B.C., war between Egypt and Persia was brewing. A Greek mercenary named Phanes of Halicarnassus had just had a falling out with the Pharaoh and went over to Persia, telling Cambyses that the trick would be to sneak into Egypt using Bedouin guides to make sure they knew the way to some sources of water on the way.

Unfortunately for Phanes, the Egyptians had suspected he was going to betray them and briefly caught him while he attempted desertion. Later, a spy sent Phanes an offer to abandon the Persians again and return to their service, but Phanes could tell that of course he’d be killed immediately if he did so. Ultimately his switching sides cost him dearly, for when he led his mercenaries to the gates of Egypt’s capital, the sons he’d left behind were taken before him and their throats were slit. At least Phanes had the consolation of sacking the city and then becoming one of the Persian emperor’s most trusted generals.

3. Albrecht Wallenstein

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Wallenstein was one of the few military commanders who openly approached rising through the military ranks purely as a financial move. During the 1620s, the Holy Roman Empire found itself at war with Protestants from Germany, France, and Britain, so Emperor Ferdinand needed more troops. Wallenstein offered to raise an army from his Bavarian lands, but being independently wealthy, the ostensibly Imperial army stayed his because he paid the wages. Wallenstein basically saved the Empire but the emperor distrusted him and, after Wallenstein enraged much of Europe by issuing an edict that would seize hundreds of Protestant churches and make them Catholic property, fired him. Sweden sent an army to invade the Empire and the newly independent Wallenstein had the nerve to offer an army of 12,000 troops to the Swedish king Gustavus Adolphus if he could stay in charge of it. In the end, Wallenstein ended up being rehired by Ferdinand and his army killed the king he’d just offered an army to at Luetzen, but Wallenstein was assassinated a few years after that.

2. Frank Crawford Armstrong

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During the American Civil War, he was initially a commander for the Army of the Potomac with the Union. In 1861 he fought at the Battle of Bull Run, effectively the battle that made the Civil War as a prolonged conflict possible by being a disastrous Southern victory, and shortly after he apparently decided to switch sides. Armstrong at least had the courtesy to attempt to go through official channels and tried to resign his commission with the Northern army before joining the Southern one. His resignation took three days, so he’d already been given an officer’s commission before his original one ended, meaning that for a time he was listed as a soldier by both sides. His service for the South was pretty long and distinguished, with the famous general/KKK founder Nathan Bedford Forrest praising the performance of his troops. Nothing if not flexible, after the war he worked for a mail company in Texas then worked as a commissioner of Indian Affairs.

1. Benedict Arnold

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The inclusion of this entry isn’t surprising anyone, but perhaps it’s surprising to learn what a hero for the American Revolution Arnold was until he became the embodiment of treachery. He helped win a vital victory at Fort Ticonderoga, then stopped the British from seizing control of New York in 1775 by stopping their fleet with his much smaller one at Lake Champlain. Most important was that at the Battle of Saratoga he disobeyed the orders of General Horatio Gates, who’d recently tried to relieve him of command, and launched a daring assault which defeated the British forces and was largely rewarded with a bullet in the leg and the news his wife had died.

Feeling betrayed by the continental forces, he offered the British Army the American stronghold of West Point for some cash and a commission. The effort failed, but Arnold escaped and was given a job anyway. Benedict Arnold was not trusted with a very prominent role by his new British commanders. Indeed, pretty much all he accomplished was further tarnishing his name by commanding raids on Colonial civilians which included burning down Richmond, Virginia. In 1783, when the war officially ended, he moved to Britain and eventually died destitute in 1801.

Dustin Koski will never betray Top Tenz, but you’d better follow him on Facebook just so you can make sure.


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