12 Generals You Won’t Believe Switched Sides and Defected to the Enemy

Alcibiades

Alcibiades (450 – 404 BC) was a brilliant and unscrupulous Athenian politician and general, and was the most dynamic, fascinating, and catastrophic Athenian leader of the Classical era. Born into a wealthy family, his father was killed when Alcibiades was a toddler, and raised without firm guidance, Alcibiades grew into a self-indulgent man, whose gifts of brilliance and charm were counterbalanced by self centeredness, irresponsibility, extravagance, and debauchery.

Early in the Peloponnesian War against Sparta, Alcibiades won a reputation for courage and military talent. By 420 BC he had become one of Athens’ generals, and in 415 BC, he persuaded Athens to invade Sicily and conquer Syracuse. Soon before departure, however, statues of the god Hermes were desecrated, and suspicion fell upon Alcibiades, whose immoral clique had a reputation for drunken vandalism and impiety. The expedition sailed to Sicily, with a cloud hanging over its leader, and when Alcibiades was eventually summoned to face trial before the Athenian Assembly, he fled and defected to Sparta.

He advised the Spartans to adopt a strategy that annihilated the Sicilian expedition – the force he had organized, convinced Athens to send to Sicily, and whose men he once led. That was the most catastrophic defeat suffered by Athens during the war, and of the tens of thousands of Athenians who took part, only a handful survived: the remainder were either killed outright, or enslaved and worked to death.

Alcibiades also persuaded the Spartans to alter their strategy of marching into Athens’ Attica region each year, burning in looting, then withdrawing and repeating the following year. Instead, he had the Spartans establish a permanent base in Attica, from which they could pressure Athens year round. He also went to Ionia, where he stirred Athens’ allies and client states into revolting.

Alcibiades wore out his welcome in Sparta, however, after he was caught in bed with Spartan king Agis II’s wife. Fleeing again, this time to the Persians, Alcibiades persuaded them to opportunistically intervene in the war in order to prolong it, and keep Athens and Sparta too busy fighting each other to challenge Persia’s interests.

Athens fell into chaos that culminated in an oligarchic coup. However, Athens’ fleet, composed predominately of the lower classes, remained pro democracy, and in the turmoil, Alcibiades managed to persuade the fleet to take him back. Between 411 – 408 BC, he led the Athenian navy to a series of stunning victories that turned the war around, and suddenly it was Sparta that was reeling and on the verge of collapse.

Alcibiades returned to a hero’s welcome in Athens, his earlier treasons forgiven and temporarily forgotten. However, the Athenians turned on Alcibiades a few months later, after a minor naval defeat during his absence from the fleet. He fled again, and having burned bridges with all sides, took refuge in Phrygia. There, a Spartan delegation persuaded Phrygia’s Persian governor to murder Alcibiades in 404 BC.

Hermann

Hermann (circa 18 BC – 19 AD) was a German tribesman in Roman service, whose switching of sides against the Romans had far-reaching historic impact, and made him a Roman villain and a German national hero. His gigantic statue and memorial, the Hermannsdenkmal, stands today near Detmold in Westphalia, close to the site of his betrayal.

Hermann rose to command an auxiliary cohort in the Roman army. He gained the respect of his employers, who bestowed Roman citizenship and high social status upon him. He was posted to the Rhine, where he served under Publius Quinctilius Varus, a Roman general married to a niece of the emperor Augustus, who ordered Varus to conquer and pacify Germania.

Varus’ arrogant treatment of the Germans, however, caused them to revolt, and Hermann decided that his loyalty lay with his people rather than his paymasters. In 9 AD, acting as guide for Varus and his army as they returned from campaigning to winter quarters, Hermann suggested a shortcut through a hilly and heavy forested region, and lured them into an ambush in the Teutoburg Forest in which three legions were annihilated. To avoid capture, Varus committed suicide.

The disaster shocked Rome, and in its aftermath, Augustus went into mourning, let his beard grow out, and took to banging his head against the wall while wailing “Quinctilius Varus, give me back my legions!” Roman plans for expansion into Germania were halted and never resumed, and Germania eventually became a springboard and highway for the barbarians who demolished the empire.

Flavius Josephus

Yosef ben Matityahu (37 – 100 AD), who went on to Latinize his name into Titus Flavius Josephus, was a Jewish general and leader who commanded the Jewish forces in Galilee at the start of the First Jewish-Roman War (66 – 73 AD), also known as the Great Jewish Revolt, before switching sides after he was captured, and joining the Romans.

The revolt had erupted in 66 AD after the Roman authorities responded to tax protests by arresting prominent Jews and looting the Jewish Temple in Jerusalem. That heavy-handedness transformed the protests into a full-blown rebellion, which forced the Romans to flee Judea. Armed bands seized forts across the country, while in Jerusalem, which the rebels captured, a national military government was organized.

In Galilee, Josephus, a 29-year-old priest, was chosen to lead. With a combination of guile and force – such as his bluffing the town of Tiberias into surrender with an overwhelming display of force from a navy of 230 boats that, unbeknownst to the Tiberans carried no more than five men each – he managed to bring Galilee under his control.

After its early setback, however, the Empire struck back, and the Roman general Vespasian was appointed to crush the revolt. Vespasian, with his son Titus, marched his legions from Syria into Judea, with Galilee as his first stop. Josephus gathered an army, but its undisciplined ranks broke and ran at the first sight of the Roman legions, and fled to the hilltop town of Jotapata. There, Vespasian surrounded Josephus and his men, and after a 47-day siege, successfully stormed the town.

Josephus and the rebel leaders fled to a secret hiding place down a well, but a prisoner told the Romans, who shouted an offer down the well for Josephus to surrender, as Vespasian wanted him alive. Josephus wanted to surrender, but the other leaders insisted that they all commit suicide instead. So Josephus suggested they do so in an orderly fashion, by drawing lots, with the loser of each round getting killed by the others. Josephus rigged the lots, as one by one the leaders were killed until he was one of only two men left alive, at which point he convinced the other survivor that they should surrender. They did, and while the other man was summarily executed, Josephus was taken in shackles to Vespasian.

There, claiming to be a prophet, Josephus told the Roman general that he had a vision in which he saw Vespasian as emperor. Vespasian, who was already pondering a revolt, spared Josephus’ life and kept him as a prisoner. In 69 AD, following Nero’s ouster and suicide, 3 Roman generals had followed in quick succession as Roman emperors, and Vespasian decided that he should be the fourth. He led a successful revolt that put him on the throne, and recalling Josephus’ prophecy, ordered him freed.

While Vespasian sailed off to Rome, Josephus joined Vespasian’s son, Titus, in besieging Jerusalem and finishing off the revolt. After a horrific siege, the city fell in 70 AD, and Titus ordered Jerusalem’s complete destruction, while tens of thousands of prisoners were sold off as slaves or forced to fight to the death in games for Titus’ amusement and to celebrate his victory.

Titus then took Josephus back with him to Rome, where he held a triumphal parade featuring captive rebel leaders chained to models of their towns on floats that paraded down Rome’s street, and off to their execution sites. Josephus joined Vespasian’s household, and spent the remainder of his life writing, leaving behind a valuable history of the Jewish Revolt.

Ashikaga Takauji

Ashikaga Takauji (1305 – 1358) was a Japanese warrior, general, and statesman whose life and career featured numerous twists and turns, during which Takauji switched sides multiple times. At the end, he rose to become shogun, or military dictator, and founded the Ashikaga Shogunate at age 33, which dominated Japan for nearly two and a half centuries.

Takauji began his career in service to the powerful Hojo clan, which ran Japan’s then-Kamakura Shogunate. In 1333, Takauji was tasked by the Hojos with ending a civil war against Japan’s figurehead emperor, but he came to dislike the Hojos and switched sides, joining the emperor, instead. With Takauji’s help, the Hojos were defeated and compelled to commit suicide, ending the Kamakura Shogunate.

The emperor was restored to power and established the first imperial government that wielded both military and political power since the 10th century. For his troubles, however, Takauji was rewarded with an accusation of having murdered an imperial prince while campaigning. He responded by switching sides once again, and turning on the emperor whom he had only recently restored to the throne. He defeated the emperor, reducing him once again to a figurehead, and assumed the military dictatorship of Japan, founding the Ashikaga Shogunate, which ruled the country from 1338 to 1573.

Contemporary Japanese intellectuals credited Takauji’s success to three factors. First, calm courage in battle, during which exhibited no fear of death. Second, mercy towards defeated foes and tolerance, which often meant that surrender was a viable option for his opponents. Third, an open handed generosity to subordinates, which earned and cemented their loyalty.

John Hawkwood

Sir John Hawkwood, Italian byname Giovani Acuto, meaning “John the Astute” (1320 – 1394) was an English soldier of fortune who plied his trade in Italy as a condotierre. As captain of a powerful mercenary band, Hawkwood played a significant role in 14th century Italy’s wars and politics, and switched sides on numerous occasions between the peninsula’s competing factions and states.

Hawkwood began his military career during the Hundred Years War in the armies of England’s king Edward III, who knighted Hawkwood for exceptional service. When that war was temporarily interrupted by a peace treaty in 1360, Hawkwood left for Italy at the head of a company of mercenaries, and joined the English unit known as the White Company.

In 1364, he was elected captain-general of the White Company, and he elevated its reputation, transforming it into an elite and highly sought after mercenary unit by adopting the English longbow and tactics successfully used in France, lightened his men’s armor and equipment, which made them famous for the rapidity of their movements, and instilled strict discipline.

During the 1370s, he served the Pope, but when the Holy Father stiffed Hawkwood on payment, the mercenary bided his time, and when the Pope sent him to put down a rebellion in Citta di Castello, Hawkwood captured and kept the city in order to compel payment. Strapped for cash, the Pope was forced to invest Hawkwood with the city, granting it to him in return for uncompensated services.

Between 1372 and 1378, Hawkwood repeatedly switched sides between serving the Pope and his rival, the duke of Milan, whose illegitimate daughter he married in 1377. In 1378, after quarreling with his new father in law, Hawkwood switched sides and signed a contract with Milan’s rival, the city of Florence, and was appointed its captain-general. He remained in Florence until he finally decided to sell his Italian properties and retire to England to spend his last years, but died in 1394 before he could do so.

Francesco I Sforza

Francesco Sforza (1401 – 1466) was an Italian condottiero, or soldier of fortune. During a lifetime filled with twists and turns, he became a mercenary general, turned on his employers and switched sides multiple times. Finally, he made himself Duke of Milan, founding the Sforza Dynasty which ruled that city and strongly influenced northern Italy and Italian politics for a century.

Sforza was the illegitimate son of a mercenary commander and accompanied his father on campaigns starting at age 17. He quickly developed a reputation for toughness and strength, and became famous for his ability to bend metal bars with his bare hands. Following his father’s drowning during battle, against a rival in 1424, Sforza took command. He proved himself a brilliant tactician and battlefield commander, went on to win the battle, and killed his father’s rival in the process.

He then signed on to fight for multiple Italian rulers, including the Pope, the Neapolitans, and duke Visconti of Milan. Sforza fought alternately for and against these groups during the next two decades. During one of the intervals when he got along well with Milan’s duke, he betrothed Visconti’s illegitimate daughter and only child in 1433.

The following year, however, Sforza switched sides and left the duke of Milan’s employ for that of his rival, Cosimo de Medici of Florence. In 1438, Sforza fought for Florence against his prospective father in law, and inflicted crushing defeats on Milan. In 1441, he patched things up with Milan’s duke, and finally married his daughter. But two years later, in 1443, he again switched sides and fought against his now-father-in-law.

When the duke of Milan died in 1447 without a male heir, the Milanese rebelled and proclaimed a republic, and hired Sforza as their military commander. A three-sided struggle then ensued between the Milanese republic, the rival city of Venice, and Sforza. When the Milanese signed a peace treaty with Venice in 1449 against Sforza’s wishes, he turned on his employers and switched sides, this time backing himself. He besieged Milan, starving it into submission, and entered the city in 1450 as its new duke.

Francesco Sforza’s shrewdness, opportunism, and successful deviousness made him the exemplar and model of Machiavelli’s prince. He won his state by his exceptional ability and skill rather than through luck or inheriting it by winning the lottery at birth. He then went on to consolidate his gains and secure them sufficiently to found a dynasty.

Albrecht Wallenstein

Albrecht Wenzel Eusebius von Wallenstein (1583 – 1634) was a Protestant Bohemian soldier who approached soldiering and war as financial transactions and business moves. He rose to command the armies of the Holy Roman Empire during the Thirty Years War, fought for the Catholics before switching sides to the Protestants, then switched back to the Catholics once again.

Born a Lutheran, Wallenstein was orphaned at age 13 and raised by an uncle who saw to his education. In 1604, he fought for the Habsburgs and ingratiated himself with them and the influential Jesuits at their court by nominally converting to Catholicism. His Jesuit confessor arranged for him to marry a fabulously wealthy elderly widow with huge estates, which wealth and lands Wallenstein inherited after her death in 1614, instantly vaulting him into the ranks of the powerful in the Habsburg realms.

He fought in numerous campaigns and battles, and earned a reputation for military brilliance. At the outbreak of the Thirty Years War, the Habsburgs feared that they would end up facing the Protestant-born Wallenstein. But calculating that serving the Catholics would prove more lucrative, Wallenstein offered his services and an army of 30,000 to 100,000 to the Holy Roman Emperor Ferdinand II.

Wallenstein then proceeded to thoroughly destroy Protestant armies and the Protestant cause in his native Bohemia. Particularly at the Battle of White Mountain in 1620, so as to eradicate two centuries of a strong Protestant tradition, dating back to Jan Hus’ uprising in the early 1400s. From a Protestant stronghold in Central Europe, Bohemia was transformed into a Catholic bastion, and it remains Catholic to this day.

Wallenstein then proceeded to wreck the Protestant cause in western and northern Germany, but his successes and ambition, plus fears that he was preparing to switch sides, led Emperor Ferdinand to remove him from command in 1630. The Protestants recovered, and particularly under Swedish king Gustavus Adolphus, won a series of stunning victories. Reasoning that a potentially treasonous general was better than incompetent ones, the Emperor recalled Wallenstein. Wallenstein stabilized the situation by defeating Gustavus Adolphus at the Battle of Alte Veste in 1632, and killed him at the Battle of Lutzen later that year.

However, Wallenstein grew increasingly resentful of his treatment by Ferdinand, and did little to hide his intent to switch sides and defect to the Protestant cause by joining the Swedes, as soon as he negotiated an agreeable deal. Word got back to the Emperor of Wallenstein’s planned defection, however, so he nipped the problem in the bud by having the problematic general assassinated in 1634.

Shi Lang

Shi Lang, Marquis Jinghai (1621 – 1696) was a Chinese admiral who served the Ming Dynasty, before switching sides and turning against his people. He defected to help the Manchu invaders in their successful conquest of China, overthrow of the Ming Dynasty, and its replacement with the Manchu Qing Dynasty which ruled China until the early 20th century.

Shi Lang was born into a prominent family in Fujian, studied the military arts, and gained an expertise in naval warfare. He joined the Ming navy, which was led by the powerful Zheng family and quickly distinguished himself. Lang rapidly rose to command a powerful contingent by his mid-20s. A falling out with a scion of the Zhengs led Shi Lang to defect to the rising Manchus in 1646. The Zhengs retaliated by slaughtering the family he left behind as traitors, killing Shi Lang’s father, brother, and son.

The Manchus, who lacked a seafaring tradition and capable naval commanders, warmly welcomed Shi Lang for his naval talents and network of contacts throughout East Asia’s port cities. In 1656, he helped the Manchus conquer his native province of Fujian. Later, in 1663, he conducted a successful campaign against the Zheng family, in cooperation with a naval contingent from the Dutch East India Company.

In 1681, he led the Manchu invasion of the Ming Dynasty’s last bastion in Taiwan which gave him great personal satisfaction. He once again defeated the Zheng family, crushing their leading admiral in a sea battle off the Pescadores, and forcing the final surrender of his old enemies. After conquering Taiwan for the Manchus, Shi Lang was given the hereditary rank of marquis, and granted the title of “General Who Maintains Peace on the Seas”.

Benedict Arnold

Benedict Arnold (1741 – 1801) is America’s most notorious turncoat, whose name became an epithet, synonymous with treason. He had played a leading role early in the American War of Independence from Britain, and had probably been the rebelling patriots’ most capable general and combat commander, before resentments over slights, coupled with financial distress, led him to switch sides.

Before his treason, Arnold had fought valiantly for the revolutionaries. Early in the conflict, he even played a leading role in capturing Fort Ticonderoga. He then led an expedition through difficult terrain in an attempt to capture Quebec, and although the expedition ultimately failed, it demonstrated great leadership skills on Arnold’s part that he even managed to get his force to the outskirts of Quebec.

In 1776, a creative Arnold constructed a fleet from scratch at Lake Champlain, with which he defeated a superior British fleet. While proclaimed a hero, he also aroused the resentment and jealousy of fellow officers, who began a whispering campaign to tarnish his name. In 1777, Congress created five new major generals, and Arnold was aghast upon discovering that his name was not on the list while some of his juniors were.

He was kept from resigning only by personal pleas from George Washington. A short time later, after defeating a British advance into Connecticut, Arnold was finally promoted to major general. However, his seniority was not restored, which he took as another slight. He again sought to resign his commission but was prevailed upon to remain. He performed brilliantly in thwarting the British advance from Canada into upstate New York in 1777, and was instrumental in bringing about its defeat, culminating in the British surrender at Saratoga, where Arnold suffered a serious wound.

Crippled by his injuries, he was made military commander of Philadelphia, where his socializing with loyalist families and lavish lifestyle, which he financed with questionable dealings, led to scandal. His marriage to a much younger woman of loyalist sympathies and extravagant spending habits soon pushed him into debt, and between stewing over slights and his increasing financial difficulties, Arnold secretly approached the British, offering to switch sides.

After his stint in charge of Philadelphia, Arnold was put in command of West Point, a fortified position on the Hudson river, upstream from British-occupied New York City. West Point barred the British from sailing upriver. Arnold schemed to sell the British plans of the fortifications, and to help deliver them into their hands, for £20,000. However, his British contact, major John Andre, was captured, along with documents incriminating Arnold, who barely escaped ahead of arrest.

Arnold was then made a brigadier general in the British army, and led Redcoats against his former comrades. His new masters never warmed to him however, and he was unable to secure a regular commission in the British Army after the war. After the conflict’s end, he engaged himself in a variety of enterprises, including privateering and land speculation in Canada, before finally settling in London, where he died in 1801.

Bernadotte

Jean-Baptiste Jules Bernadotte (1763 – 1844) was a French Revolutionary general who was granted high rank and honors by Napoleon Bonaparte. Bernadotte returned the favor by switching sides, and at the head of a Swedish army, helped defeat Napoleon at the Battle of Leipzig in 1813, the Napoleonic Wars’ largest and bloodiest single engagement, whose lose effectively sealed Napoleon’s fate.

The son of a prosecutor, Bernadotte enlisted in the French army at age 17. When the French Revolution erupted, he became an ardent supporter. Within two years, between 1792 and 1794, he experienced rapid promotions from sub-lieutenant to brigadier general in the Revolutionary armies. Campaigning in the Low Countries, Germany, and Italy, he developed a reputation as a disciplinarian who kept his troops under tight control, and in 1796 he played a key role in saving the French army in Germany from destruction following its defeat by the Austrians and ensured its safe retreat across the Rhine.

Bernadotte first came in contact with Napoleon in 1797, and the pair developed an early friendship, which eventually frayed and broke as a result of rivalries and misunderstandings. While relations between the two were still good, however, Napoleon recognized Bernadotte’s talents, and in 1804 – following his declaration of empire and Bernadotte’s declaration of loyalty to him – Napoleon appointed him a Marshall of France.

Following the successful 1805 Ulm Campaign and victory at the Battle of Austerlitz, Napoleon further rewarded Bernadotte by making him Prince of Ponto Corvo in Italy. Things began to sour between the two, however, during the Prussian campaign in 1806, when Napoleon severely criticized Bernadotte for failing to bring his corps to the fight at the hard-fought battles of Jena and Auerstadt, and barely refrained from court-martialing him for dereliction of duty. The relationship was sundered at the 1809 Battle of Wagram, after which Napoleon relieved Bernadotte of command for his poor handling of his troops during the fight. Napoleon sent him back to Paris under the face-saving guise of “health reasons”.

Things soon looked up for Bernadotte, however, when the childless and ill king Charles XIII of Sweden, a French ally and client state, adopted him in 1810 and made him Crown Prince and heir to the throne. Bernadotte assumed the regency and governance of Sweden, and cast about for an accomplishment to solidify his authority and future dynasty.

The opportunity came when Napoleon was weakened following the destruction of his Grande Armee after his catastrophic invasion of Russia in 1812. In 1813, Bernadotte switched sides, signed a treaty with Britain, and declared war on France. He landed a Swedish army in northern Germany, and in alliance with the Austrians, Russians, and Prussians, got his payback against Napoleon by helping defeat him in the war’s biggest and bloodiest battle, at Leipzig, in 1813. After the war, he returned to Sweden, where he established the Bernadotte Dynasty, whose royal family reigns in Sweden to this day.

Andrey Vlasov

Andrey Andreyevich Vlasov (1900 – 1946) was one of Joseph Stalin’s favorite Red Army generals, who turned on the Soviet dictator during WWII and switched sides after his capture by the Germans in 1942. Throwing in his lot with the Nazis, Vlasov turned coat and fought with the Germans against the Soviet Union at the head of the so-called Russian Liberation Army.

Vlasov had been drafted into the Red Army in 1919 and fought in its ranks during the Russian Civil War, during which he distinguished himself. Rising steadily through the officer ranks, he earned a reputation for his ability to whip poor units into shape. In 1930, Vlasov gave his career a boost by joining the Communist Party, and in 1938, he was sent to China as a Soviet military advisor to its generalissimo, Chiang Kai-Shek.

When the Nazis invade the USSR in 1941, Vlasov was a mechanized corps commander in the Ukraine and was one of the few generals who managed to get his unit to safety, as he successfully fought his corps out of multiple encirclements. His skill and aggressiveness brought him to Stalin’s attention, who summoned him in November of 1941 and promoted him to command an army in Moscow’s defenses.

Vlasov and his army played a key role in keeping the Germans out of Moscow, and in January, 1942, he spearheaded the counteroffensive that pushed the Germans 100 miles from the Soviet capital. He earned decorations and acclaim in so doing, plus Stalin’s admiration, who promoted him to deputy commander of the Volkhov Front, 300 miles northwest of Moscow.

Later, he was put in charge of the 2nd Shock Army after its commander fell ill, but it got cut off and encircled as it advanced towards Leningrad, and was destroyed in June 1942. Vlasov escaped temporarily but was captured 10 days later. In captivity, he agreed to switch sides. Taken to Berlin, he and other Soviet traitors began drafting plans for a Russian provisional government and for recruiting a Soviet turncoat army.

In 1943, he wrote an anticommunist leaflet, millions of copies of which were dropped on Soviet positions. Using Vlasov’s name, the Nazis recruited hundreds of thousands of Soviet defectors, forming them in a so-called Russian Liberation Army, but although they were nominally under Vlasov’s command, they were kept strictly under direct German control, with Vlasov exercising little or no authority.

His only combat against the Red Army took place while in charge of a turncoat division near the Oder river in February of 1945, during the war’s closing stages, after which he was forced to retreat to German-controlled Czechoslovakia. There, in May of 1945, a few days before war’s end, Vlasov’s division turned coat once again, this time against the Germans and in support of a Czech uprising.

At war’s end, he attempted to escape to the Western Allies’ lines but was captured by Soviet forces, who discovered him hiding under blankets in a car. He was flown to Moscow and held in its dreaded Lubyanka prison, where he underwent torture for months. He was tried for treason in the summer of 1946 along with 11 of his leading subordinates. All were found guilty and sentenced to death, and on August 1st, 1945, Vlasov and his fellow turncoats were hanged.