Turncoat Generals – Commanders From History Who Switched Sides

19. Josephus Was One of the Jewish Revolt’s Most Brilliant Commanders

Josephus, a 29-year-old priest, was chosen to lead the rebel forces in Galilee. He used a combination of guile and force to bring the region under his control. In one ruse, he bluffed the town of Tiberias to surrender with an overwhelming display of force from a navy of 230 boats. Unbeknownst to the Tiberans, the boats carried no more than five men each. After early setbacks, however, the Empire struck back, and the Roman general Vespasian was sent 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.

18. Cheating Death With a Rigged Lottery

Vespasian surrounded Josephus and his men at Jotapata, and after a siege that lasted 47 days, successfully stormed the town. Josephus and other rebel leaders fled to a secret hiding place down a well, but a prisoner told the Romans. The victors shouted an offer down the well for Josephus to surrender, as Vespasian wanted him alive. He 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. He rigged the lots, and one by one the other leaders were killed, until Josephus was one of only two men left alive. At that 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.

17. From Rebel Commander to Prophet

When he was brought before Vespasian, Josephus claimed that he had a gift for prophecy and that he could see into the future. He told the Roman general that he had a vision in which he saw Vespasian as emperor. Vespasian, who was already contemplating a revolt, liked Josephus’ prophecy. So he spared his life and kept him as a prisoner. In 69 AD, after the ouster and suicide of Emperor Nero, three Roman generals followed in quick succession as Roman emperors. 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.

16. The Great Jewish Revolt’s Greatest Turncoat

While Vespasian headed to Rome, Josephus joined the new emperor’s son, Titus, in besieging Jerusalem and finishing off the revolt. After a horrific siege, the city fell in 70 AD. Titus ordered Jerusalem’s complete destruction, and tens of thousands of prisoners were sold off as slaves or forced to fight to 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 that featured captive rebel leaders chained to models of their towns on floats that paraded down Rome’s streets, before they were executed. Josephus joined Vespasian’s household, spent the remainder of his life writing, and left behind a valuable history of the Great Jewish Revolt.

15. The Soviet Union’s Most Infamous Turncoat

Andrey Andreyevich Vlasov (1900 – 1946) is the USSR’s most infamous turncoat and traitor. He had been one of Stalin’s favorite generals early in World War II. Vlasov went from golden boy to redheaded stepchild when he switched allegiance after his capture by the Germans in 1942. Throwing in his lot with the Nazis, Vlasov went from hero to reviled turncoat when he fought against his countrymen at the head of the so-called Russian Liberation Army. His military career  had started in 1919, when he was drafted into the Red Army. He fought in its ranks during the Russian Civil War that followed the communists’ seizure of power in 1917, and distinguished himself. He rose steadily through the officer ranks, and became known for his ability to whip poor units into shape. In 1930, Vlasov gave his career a boost by joining the Communist Party.

14. A Brilliant Commander Who Earned Stalin’s Admiration

Vlasov was sent to China on 1938 as a Soviet military advisor to its generalissimo, Chiang Kai-Shek. Vlasov was a mechanized corps commander in Ukraine when the Nazis invaded the Soviet Union in 1941. He was one of the few generals who managed to get their units to safety, as he successfully fought his corps out of multiple encirclements. Such skill and aggressiveness brought Vlasov to Stalin’s attention. The Soviet dictator summoned him to the Kremlin in November, 1941, and promoted him to command an army in Moscow’s defenses. Vlasov played a key role in keeping the Germans out of the Soviet capital.  In January, 1942, he spearheaded a counteroffensive that pushed the Germans 100 miles from Moscow. Vlasov earned decorations and acclaim, plus the admiration of Stalin, who promoted him to deputy commander of the Volkhov Front, 300 miles northwest of Moscow.

13. Switching Sides from the Communists to the Nazis

Vlasov was eventually put in charge of the 2^nd Shock Army after its commander fell ill. However, his army got cut off and encircled as it advanced towards Leningrad, and was destroyed in June, 1942. Vlasov escaped temporarily, but was captured ten days later. In captivity, he agreed to become a turncoat and switch sides. Taken to Berlin, he and other Soviet traitors drafted plans for a Russian provisional government and for the recruitment of a Soviet turncoat army. Vlasov wrote an anticommunist leaflet in 1943, of which millions of copies were airdropped on Red Army positions. Using Vlasov’s name, the Nazis recruited hundreds of thousands of Soviet defectors for a so-called Russian Liberation Army. The Russian turncoats were nominally under Vlasov’s command, but he exercised no real authority, as the men were kept strictly under direct German control.

12. The Painful End of a Turncoat

Vlasov’s only combat against the Red Army took place while in charge of a turncoat division near the Oder River in February, 1945, in the war’s closing stages. Afterwards, he was forced to retreat to German-controlled Czechoslovakia. In May, 1945, a few days before WWII ended, Vlasov’s division turned coat once again, this time against the Germans and in support of a Czech uprising. At war’s end, Vlasov tried 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 was tortured for months. He was tried for treason in the summer of 1946 along with eleven of his leading subordinates. All were found guilty and sentenced to death, and on August 1^st, 1945, Vlasov and his fellow traitors were hanged.

11. America’s Most Infamous Turncoat

American Revolutionary War General Benedict Arnold (1741 – 1801) is the most infamous turncoat in the history of the United States. Indeed, his name has become an epithet, synonymous with treason and betrayal. That was a dramatic turn from his early war career, when he had been a prominent Patriot hero. Arnold had been highly regarded in the fight against the British, and was perhaps the American side’s most capable combat leader. That all changed when a combination of resentments over slights, coupled with financial distress, led him to turn traitor. Before that, however, Arnold had provided valuable service to the Americans, and played a key role early in the war in the capture of Fort Ticonderoga. He then led an expedition through extremely rough terrain in an attempt to capture Quebec.

10. Brilliant Success that Aroused Jealousy

The Quebec Expedition ultimately failed. However, to even get his men to the outskirts of Quebec exhibited great leadership on Benedict Arnold’s part. In 1776, he demonstrated his enterprise when he constructed a fleet from scratch at Lake Champlain. With it, the Patriots defeated a vastly superior British fleet. While lionized as a hero by the public, Arnold’s successes, rash courage, and driving style aroused the jealousy and resentment of other officers, who backbit and schemed against him. When Congress created five new major generals in 1777, Arnold was stung when he was bypassed in favor of some of his juniors. Only George Washington’s personal entreaties prevented his resignation. Soon thereafter, Arnold successfully beat back a British attack in Connecticut, and was finally promoted to major general. However, his seniority was not restored – another slight that ate at him.

9. Growing Resentment Against the Patriots

Offended that his seniority was not restored, Benedict Arnold once again sought to resign, but was prevailed upon to remain. He performed brilliantly in halting the British advance into upstate New York in 1777, and played a key role in its defeat. It culminated in the British surrender at Saratoga, where Arnold fought courageously and suffered a serious leg wound. Crippled by his injury, Arnold was put in charge of Philadelphia. There, he began to socialize with families loyal to the British. He took to an extravagant life with lavish expenditures, financed through questionable methods that led to scandal. Arnold also married a much younger woman of loyalist sympathies, and her spendthrift habits soon drove him deep into debt. Between resentments and financial difficulties, he secretly approached the British to offer his services. As seen below, Arnold was perfectly positioned to deal the Patriots a fatal blow.

8. A Terrible Betrayal Thwarted at the Last Minute

Benedict Arnold had been placed in charge of American fortifications at West Point on the Hudson River. Upstream from occupied New York City, the fortifications barred the British from sailing upriver. Arnold plotted to sell the fortification’s plans to the enemy, and contrived to deliver them into British hands for £20,000. However, his British contact was captured, along with documents that incriminated Arnold. He fled just in time to evade arrest. Arnold was made a brigadier general in the British Army, and led soldiers against the Patriots for the rest of the war. The British never fully warmed to him however, and he was unable to secure a regular commission after the war. He pursued a variety of ventures, including privateering and land speculation in Canada, before he finally settled down in London, where he died in 1801.

7. A Commander Who Kept Switching Sides

Albrecht Wenzel Eusebius von Wallenstein (1583 – 1634) was a Protestant Bohemian soldier who treated soldiering and war as financial transactions and business moves. He commanded the Holy Roman Empire’s armies during the Thirty Years War, fought for the Catholics, turned coat to join the Protestants, switched back to the Catholics once again, and only his sudden death prevented his turning coat for a third time. Born a Lutheran, Wallenstein was orphaned at age thirteen and raised by an uncle who saw to his education. In 1604, he fought for the Hapsburgs 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. Her wealth and lands, which Wallenstein inherited after her death in 1614, instantly vaulted him into the ranks of the Hapsburg realm’s most powerful figures.

6. Securing Protestant Bohemia for Catholicism

Wallenstein fought in numerous campaigns and battles, and earned a reputation for military brilliance. At the outbreak of the Thirty Years War, the Hapsburgs feared having to face the Protestant-born Wallenstein. However, Wallenstein calculated that siding with the Catholics was more profitable, so he offered his services and an army of 30,000 to 100,000 to Holy Roman Emperor Ferdinand II. Wallenstein then proceeded to destroy Protestant armies and the Protestant cause in his native Bohemia. He did that so thoroughly, particularly at the Battle of White Mountain in 1620, so as to eradicate two centuries of a powerful Protestant tradition that dated back to Hussite Wars in the early 1400s. From a Protestant stronghold in Central Europe, Bohemia became a Catholic bastion, and remains Catholic to this day. Wallenstein then proceeded to wreck the Protestant cause in western and northern Germany.

5. Nipping Another Coat Turn in the Bud

Wallenstein’s success and ambition, plus fears that he was about to turncoat, led Emperor Ferdinand to remove him from command in 1630. The Protestants recovered, and particularly under Sweden’s King Gustavus Adolphus, won a series of stunning victories. Ferdinand reasoned that that a potentially treasonous general was better than incompetent ones, and recalled Wallenstein. He 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. He 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 Ferdinand that Wallenstein planned to turncoat, however, so he nipped the problem in the bud by having the problematic general murdered in 1634.

4. The Adventurous Life of an Ancient Turncoat

Few have lived as adventurously as Phanes of Halicarnassus (flourished sixth century BC). A Greek mercenary general, Phanes rose high in service to Egyptian Pharaoh Amasis II (570 – 524 BC). However, he turned on his employers, and turned coat during a war between Egypt and Persia. He abandoned the Egyptians, joined the army of Persia’s King Cambyses II, and played a key part in the defeat of his former employers and paymasters. The conflict between a then-declining Ancient Egypt and a rising Persian Empire was reportedly instigated by a disgruntled Egyptian physician in the Persian court. He was upset that Amasis had picked him, out of all of Egypt’s physicians, to get dragged away from his family and sent to Persia when Cambyses wrote the pharaoh asking for an eye doctor. So the angry ancient ophthalmologist schemed to get his revenge.

3. An Angry Ophthalmologist

The disgruntled Egyptian physician advised Cambyses to ask for Amasis’ favorite daughter. He knew that a request from Cambyses for the hand of the pharaoh’s daughter would put the Egyptian ruler in a bind. Amasis could accept and grow wretched at the loss of his daughter, or refuse, and offend Cambyses. Amasis did not want to send his beloved daughter to Persia. Especially since he knew that Cambyses wanted her for a mere concubine, not a wife. However, he was also intimidated by Persia’s power. So he fudged, sent a former pharaoh’s daughter, and falsely claimed that she was his. That backfired. Soon as she reached Persia, the former princess told Cambyses that Amasis had tried to fob him off with somebody else’s daughter. That greatly upset Cambyses – who was itching for an excuse to conquer Egypt, anyhow.

2. A Disgruntled General’s Flight to the Enemy

Cambyses declared war and prepared to invade Egypt. As Amasis gathered forces and prepared his kingdom’s defenses, he managed to offend Phanes. The disgruntled Greek general turned coat, and set out to join Cambyses. Reaching him turned out to be more adventurous than Phanes had expected. The pharaoh sent assassins to kill or capture Phanes before he joined his enemies. After a harrowing flight that included an escape from captivity by getting his guards drunk, Phanes reached Cambyses, who was trying to figure out the best invasion route into Egypt. Phanes recommended a route through Arab tribal lands. He advised the Persian king to seek safe passage from their rulers, and to sweeten the request with generous gifts. Cambyses heeded Phanes’ advice, and the Arabs gladly granted him and his armies safe conduct through their territory.

1. A Thorough Revenge

Before the Persians reached Egypt, Pharaoh Amasis had died, and was succeeded on the throne by his son, Psamtik III. Enraged at Phanes, Psamtik tricked the mercenary general’s sons to meet with him, took them captive, and had them executed. He then ordered their blood drained and mixed with wine, which he quaffed down and made his subordinates drink as well. Phanes got his revenge by leading the Persian army into Egypt, and acting as Cambyses’ guide and military advisor. The Persians defeated Psamtik, and forced him to retreat to his capital, where they besieged and eventually captured him. Phanes then engineered the execution of his sons’ murderer by uncovering and informing Cambyses of a plot by the captive pharaoh to stir up a revolt.

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Where Did We Find This Stuff? Some Sources and Further Reading

Andreyev, Catherine – Vlasov and the Russian Liberation Movement (1987)

Arnold, Isaac Newton – The Life of Benedict Arnold: His Patriotism and His Treason (1880)

Briant, Pierre – From Cyrus to Alexander: A History of the Persian Empire (2002)

Encyclopedia Britannica – Benedict Arnold

Encyclopedia Britannica – First Jewish Revolt

Gonick, Larry – Cartoon History of the Universe II (1994)

Herodotus – The Histories, Book 3

History Collection – 25 Reasons Why George Washington Was the Most Fascinating President in American History

Mann, Golo – Wallenstein, His Life Narrated (1976)

Military Heritage Magazine, Spring, 2013 – Wallenstein: Generalismo

Thorwald, Jurgen – The Illusion: Soviet Soldiers in Hitler’s Armies (1974)