Of Heroes and Traitors — Seven Great Generals Who Switched Sides in Wartime 

Benedict Arnold conspires with the British to surrender West Point. He will go down in history as America’s most hated turncoat.

“For some who change sides, it is a shrewd political move that puts them on the path to hero status. Others find that they have squandered any hope of esteem and a glorious reputation.”

By Douglas Brown

EVERYONE LOVES a hero; traitors are almost universally scorned.

Over the centuries, many famous military leaders have found it necessary to play politics and change allegiances either before, during or after wars.

If these defectors wind up on the winning side, posterity tends to forgive their actions. For the losers, however, everlasting ignominy awaits.

Here are seven formidable commanders who nevertheless changed sides.

The Athenian army is destroyed at Syracuse. (Image source: WikiMedia Commons)

Alcibiades

Alcibiades was a brilliant, but mercurial and debauched, general during the Peloponnesian War – the storied 27-year struggle between Athens and Sparta that rocked the Hellenic world between 431 and 404 BC.

Once he gained the clout to serve Athens as a general, Alcibiades persuaded the powerful city-state to send him as one of three commanders in an all-in expedition to Syracuse in Sicily in 415 BC. Shortly before the expedition set sail, someone defaced the statues of the god Hermes all across Athens. It was a shocking sacrilege that seemed designed to curse the city.

When Alcibiades’ political enemies publicly blamed him for the scandal, the general was recalled to face trial for the crime. Instead, he fled to Sparta and informed the rulers there of the whole Athenian strategy for Syracuse. The expedition ended in catastrophe for Athens.

After years of waging vicious war against Athens, Alcibiades tired of the rigorous Spartan lifestyle and contrived to be recalled to command an Athenian fleet. With two great victories for his old city, he again turned the tide of the war. He received a jubilant welcome back to Athens.

Then his drinking buddy whom the general had left in command lost a fleet action disastrously. Amid the political fallout, Alcibiades fled once more, this time to a secluded fortress on the Sea of Mamara to go it alone. Before the last sea battle of the war at Aegospotami, he tried to assist the Athenian fleet once more. It snubbed him and lost the battle—and the war.

Carthage would eventually be crushed at the Battle of Zama. A former ally would help deliver the final blow for Rome. (Image source: WikiMedia Commons)

Masinissa

Light cavalry, especially the elite Numidians, was vital to the Carthaginian commander Hannibal’s efforts during the Second Punic War, but was also important during that war in what is now Spain. There, Hannibal’s brother Hasdrubal fought against a Roman army under Publius Cornelius and Cnaeus Cornelius Scipio. Under the leadership of Prince Masinissa of Numidia, that kingdom’s horsemen helped harass, outflank, and ruthlessly pursue the Roman force, and both Scipio’s were killed in 211 BC. Publius’s son, who would eventually become Scipio Africanus, defeated the Carthaginians, including Masinissa, at Ilipa in 206 BC.

Apparently free from a grudge against the Numidian leader for his role in his dad’s death, the younger Publius wooed Masinissa to join the Romans. It was an act of treachery that would have tragic consequences for Carthage.

Four years later, at the Battle of Zama in 202 BC, Masinissa turned the tables on his old allies. After a failed Carthaginian elephant charge on the Roman lines that saw the huge beasts run amok through Hannibal’s cavalry, Masinissa unleashed his riders. As a hard-fought infantry action raged in the center, the Numidian turncoat encircled the Carthaginians in a feat reminiscent of Hannibal’s own murderous masterstroke against the Romans at Cannae in 216 BC. The Republic’s victory over Carthage was complete. 

Richard the Lionheart confers with France’s Phillip II. (Image source: WikiMedia Commons)

Richard the Lionheart

Richard the Lionheart was one of the Medieval era’s great generals. (However, whether he achieved greatness under English or French colours depends on one’s point of view.)

His first military experience came in 1173 when he joined his mother Eleanor of Aquitaine and two older brothers, Henry and Geoffrey, in a rebellion against his father, King Henry II of England.

Although crushed by the king’s mercenaries, Eleanor’s rebellion against her husband nonetheless horrified the chroniclers of the day. Richard was the last to submit, and when the coup was over, he pledged support for his father.  

Richard was sent to France in 1176 to put down a revolt in Aquitaine, and another in 1182. This time, he fought alongside Henry II against his older brothers. He outlived his siblings to become his father’s presumptive heir.

Richard began a campaign against Philip II of France in 1187, but tensions with Henry over his inheritance coupled with Philip’s skillful diplomacy enticed Richard to join the French in 1189. Richard pursued Henry and forced his dad to accept terms. Still the heir, Richard became king upon his father’s death that same year. 

Robert the Bruce murders John Comyn in the Greyfriars church in Dumfries. (Image source: WikiMedia Commons)

Robert Bruce

It’s ironic that one of Scotland’s finest kings and generals, one who saved her during her greatest crisis in the First War of Independence, should have begun the war in 1296 defending Carlisle with his father against the Scots.

Robert’s grandfather had been passed over for the Scottish throne in 1292, and Robert felt no loyalty to the winner of that contest, John Balliol. When William Wallace began his revolt in 1297, however, Robert joined the rebels, citing his deep love of Scotland. He was even made a Guardian to succeed Wallace after the disastrous defeat at Falkirk in 1298.

In 1302, Robert submitted to the English King Edward I on the terms that the ruler would respect his “right.” But was this “right” his claim to the Scottish throne? Historians remain divided. 

For the next few years, Robert waged war on Edward’s behalf, even pursuing Wallace himself. On February 10, 1306, at Greyfriars’ Kirk at Dumfries, Robert had a conference with his rival John Comyn about Robert getting his support in a bid for the throne on his own behalf rather than Balliol’s. The meeting turned violent, and Comyn was killed. Robert now had to openly claim the throne to escape prosecution for sacrilegious murder. The second chapter of the First War of Independence is one of the greatest against-the-odds stories in history, thanks in large part to Robert’s inspired leadership.

A 1499 German illustration showing Vlad dining among the impaled corpses of his victims. In addition to sadism, treachery was another of Vlad’s quirks. (Image source: WikiMedia Commons)

Vlad III Dracula

The inspiration for Bram Stoker’s Count Dracula, Vlad III Dracula of Wallachia, was an able, if brutal, general. His fondness for butchering captives earned him the grim nickname “The Impaler.”

With his realm unhappily caught between the old Kingdom of Hungary and the rising power of the Ottoman Turks, Wallachia’s prospects seemed bleak. When his father and brother were killed in a revolt backed by the Hungarian warlord Janos Hunyadi, Vlad was forced into the arms of the Turks. He received a commission and, in the wake of Hunyadi’s defeat at Kosovo in 1448, was installed with Turkish help as Voivode (Prince) of Wallachia. After two months, he was ousted by Hunyadi’s Wallachian ally, Vladislav II.

With Hunyadi and Vladislav falling out, Dracula reconciled with Hunyadi and with Hungarian help killed Vladislav and took the throne a second time. In 1462, however, Turkish ambitions clashed with Dracula’s independent streak, so he raided into Ottoman territory. When the Turks retaliated with an overwhelming invasion, Dracula fought a skillful guerrilla and scorched-earth campaign. The Turks retreated, but when they put forward Dracula’s brother Radu as their choice for vassal ruler, Dracula’s people abandoned him. By that point, his cruelty and machinations had alienated almost the entire country.

The Hungarians arrested him, but after 12 years of imprisonment, Dracula changed his religious affiliation to Roman Catholic from Eastern Orthodox. The Hungarians then helped him take the throne of Wallachia one more time. Shortly after they left, however, Dracula was killed under very mysterious circumstances. 

The Duke of Marlborough after his most famous victory at Blenheim. (Image source: WikiMedia Commons)

John Churchill, Duke of Marlborough

One of Britain’s greatest generals, John Churchill owed much of his success to James, Duke of York. The duke got him his first English commission, and Churchill fought for him at Solebay in 1672 against the Dutch before serving him as his representative in Scotland. When the Catholic duke became King James II and a Protestant rebellion erupted against him, Churchill masterminded the defeat of the rebels at Sedgemoor in 1685. 

James continued to alienate England with pro-Catholic and autocratic policies, leading English magnates to invite the Dutch Prince William of Orange to come to England with an army and take the throne in 1688.

This time, Churchill picked Protestantism and very reluctantly abandoned James for William, who took the throne without bloodshed (in England, anyway) in the Glorious Revolution. William made him Earl of Marlborough but never really trusted him. He eventually dismissed him and charged him with treason. His successor Anne restored Marlborough and gave him command of her army, which he led to great glory in the War of Spanish Succession.

Benedict Arnold was one of Washington’s most capable commanders. Wounded in action twice, had the general perished before his infamous act of treason, he might very well remain one of America’s most beloved heroes. (Image source: WikiMedia Commons)

Benedict Arnold

It is another irony that America’s most loathed traitor did as much as anyone to win the American Revolution. In 1775, Arnold led his men in a harrowing trek through the Maine wilderness on an expedition to seize Quebec.

During the assault, he was severely wounded, but failed to capture the city. After recovering, he cobbled together a fleet on Lake Champlain to block a British invasion from Canada in 1776. The British won that engagement too, but Arnold’s stubborn resistance prevented them from pressing their victory that winter, at George Washington’s direst moment in the war. Against orders, Arnold led the decisive attack at Saratoga in 1777, the battle that helped decide the war by bringing in French military support. He was severely wounded in the action, and had he died then, he would have gone down in history as one of America’s greatest heroes.

His wound however led him to be appointed governor of Philadelphia. The rumormongering there against him and what he saw as ingratitude from prominent locals drove him to put out feelers to the British to change sides.

In secret collusion with the enemy, he was part of a plot to capture Washington. He next tried to sell the British the strategic fortress at West Point. His liaison, however, was captured, and Arnold’s treason was found out. He was forced to flee. 

“Arnold has betrayed me,” a furious Washington cried. “Whom can we trust now?”

The British certainly never trusted him fully, so one of the bravest officers in the Revolution missed out on being anyone’s hero. Arnold died in London in 1801.

Each of these generals displayed great skill in winning battles against the odds. Yet, each of them, for one reason or another, were willing to turn on their former friends and allies and fight against the cause they had originally espoused. For some who change sides, it is a shrewd political move that puts them on the path to hero status. Others find that they have squandered any hope of esteem and a glorious reputation.

Douglas Brown is a Texas-based writer who specializes in military history and historical fiction. His novel The Honorable Spy was released by Cheetah Publishing in July of 2022. Buy it on Amazon HEREFollow him on Twitter @DougBrownAuthor or Instagram at douglasbrownauthor, or like his Facebook page, “Douglas Brown – Author.

 

Sources

Barrow, G.W.S. Robert Bruce & the Community of the Realm of Scotland. Third ed. Edinburgh: Edinburgh University Press, 1988.

De Souza, Philip, Waldemar Heckel, and Lloyd Llewellyn-Jones. The Greeks at War: From Athens to Alexander. Oxford: Osprey Publishing, 2004.

Ferling, John. Almost a Miracle: The American Victory in the War of Independence. Oxford: Oxford University Press, 2007.

Florescu, Radu R., and Raymond T. McNally. Dracula: Prince of Many Faces: His Life and His Times. Boston: Back Bay Books, 1989.

Gillingham, John. Richard the Lionheart. New York: Times Books, 1978.

Goldsworthy, Adrian. The Punic Wars. London: Cassel & Co., 2000.

Hale, John R. Lords of the Sea: The Epic Story of the Athenian Navy and the Birth of Democracy. New York: Viking Penguin, 2009.

Konstam, Angus. Marlborough. Oxford: Osprey Publishing, 2010.

Salimbeti, Andrea, and Rafaela D’Amato. The Carthaginians 6th-2nd Century BC. Oxford: Osprey Publishing, 2014.

 

 

 

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