Top 10 Obscurely Terrible Traitors in History

Treason is a dark stain on history, but some traitors are more infamous than others. This list intentionally omits the usual suspects. We’re diving into the stories of lesser-known turncoats whose actions were no less treacherous. While we had to include Benedict Arnold, the man synonymous with treason, the rest are figures you might not know.

10. Benedict Arnold: The Dining Defector

Benedict Arnold’s defection during the Revolutionary War wasn’t just about switching sides; it almost crippled the American cause. His motives were a mix of debt, resentment over promotions, and plain greed. On September 21, 1780, Arnold met with British Major John André to scheme the handover of West Point, which Arnold commanded, in exchange for 20,000 pounds and a British military position.

The British aimed to capture General George Washington while he dined with Arnold at West Point. However, American forces managed to thwart the plan, and André was captured and hanged. Arnold escaped and joined the British, forever remembered as America’s most infamous traitor.

9. Horatio Gates: A Lesson in Meritocracy

Horatio Gates was both a hero to Americans and a traitor to the British. Initially commended for his service during the French and Indian War, he faced career stagnation due to his humble background. Frustrated, he resigned his commission and moved to America in 1769, reconnecting with George Washington.

When the American Revolution began, Gates joined the Continental Army. He later overshadowed Benedict Arnold at the Battle of Saratoga in 1777, where Arnold’s daring attack played a key role, but Gates received the credit. Despite later attempts to remove Washington from command and a defeat at the Battle of Camden, Gates has streets, towns, and counties named after him—a stark contrast to Arnold’s legacy.

8. John C. Pemberton: The Sudden Southerner

John C. Pemberton, a Pennsylvanian, made a controversial decision to fight for the South during the Civil War. A US Army officer for 25 years, he resigned his post in 1861 and joined the Confederacy despite his Northern roots. His wife was a Virginian, which influenced his choice.

Pemberton rose to the rank of Lieutenant General but faced defeat at Vicksburg in 1863, surrendering to Ulysses Grant. Demonstrating his dedication, he insisted on a demotion and continued fighting. Pemberton is buried in Philadelphia, making him a geographically confusing figure, as he is a Confederate leader with a statue in the South and a gravesite in the North.

7. Rose Greenhow: “The Northerners Are Coming!”

Rose Greenhow was a Confederate spy who used her social connections in Washington D.C. to gather intelligence. A Maryland native, she mingled with high-ranking military officers and their spouses, learning about Union plans.

In early 1861, she discovered the Union’s plan to strike at Manassas, Virginia. Greenhow sent a coded message to the Confederacy, hidden in the hair of a socialite disguised as a farmer. The rebels consolidated their forces and won the Battle of Bull Run. Eventually caught and exiled, Greenhow died in 1864 while running a Union blockade, returning from Europe on a fundraising mission.

6. Alfred Redl: A Very Compromising Position

Alfred Redl was the chief counterintelligence officer in the Austro-Hungarian Army from 1900 to 1912, but he was secretly a spy for Russia. Born poor, Redl rose through the ranks due to his intellect and language skills. However, he had a secret: he was gay, which Russian intelligence discovered.

The Russians blackmailed Redl, threatening to expose his homosexuality, and he began exposing Austro-Hungarian war plans and weaknesses. When military leaders realized Russia knew their secrets, they tasked Redl with finding the traitor, which he did by framing innocent officers. Eventually, sloppy Russian intelligence led to his discovery. Faced with execution, Redl committed suicide.

5. Patrick Heenan: Code-blooded

During World War II, Patrick Heenan became New Zealand’s sole traitor. Stationed in northern Malaya with the Royal New Zealand Air Force, Heenan was responsible for Japanese attacks because the enemy seemed to know the Allied recognition codes. Despite the ciphers being changed daily, they were destroying Allied aircraft.

Suspicion fell on Heenan when a warm radio was found in his quarters. Before a formal trial could be conducted, guards reportedly shot him dead. His story remains one of the most scandalous in New Zealand’s history.

4. Pierre Laval: From High Office to High Treason

Pierre Laval, a two-time Prime Minister of France, became a notorious traitor during World War II. Initially a socialist, he drifted towards right-wing extremism and helped convince the French Assembly to cede powers to Marshal Pétain, a Nazi collaborator, to form the Vichy Regime.

Convinced Germany would win the war, Laval collaborated with the Nazis, persecuting French Resistance fighters, rounding up Frenchmen for the Nazi war effort, and deporting French Jews to concentration camps. Arrested after France’s liberation, he was convicted of high treason and executed by firing squad in 1945.

3. Lee Harvey Oswald: Traitor Turned Triggerman

Lee Harvey Oswald is more known for his role in the assassination of JFK. Before that, he was a US Marine who defected to the Soviet Union, renouncing his US citizenship and claiming to know US military secrets.

After returning to America with a Russian bride, Oswald openly professed Marxism, founded the “Fair Play for Cuba” committee, and attempted to murder a high-ranking US military officer. Documents revealed that Oswald had contact with both the Russian KGB and a Cuban intelligence officer shortly before JFK’s assassination. Oswald was a traitor who was influenced by America’s enemies.

2. Mohammed Ismail: Osama bin Bieber

In 2014, British citizen Mohammed Ismail left England to join ISIS in Syria. His ISIS comrades nicknamed him “Osama bin Bieber” due to his boyish looks. However, his time with ISIS was short-lived.

After another British-born ISIS member was killed in an American drone strike, ISIS leaders blamed Ismail, suspecting him of being a double agent. Ismail allegedly confessed and was executed, becoming the first known British citizen killed for espionage by ISIS.

1. ???: The Cyber-traitors of Today & Tomorrow

Today, cyber-traitors pose an unprecedented danger. They can cause widespread chaos with a keyboard, targeting crucial businesses and infrastructure. Unlike whistleblowers, cyber-traitors cripple essential services through ransomware and supply chain disruptions.

A recent hack targeted Florida-based IT company Kaseya, spreading through 200 corporate networks. Agencies fear that compromised individuals with access to critical systems like power grids, water supplies, and nuclear weapons could aid enemies. The threat of cyber-treason is a chilling reality of the modern age.

From the dining defector to the cyber-traitors of today, these figures remind us that treason comes in many forms, with devastating consequences. Their stories serve as cautionary tales, highlighting the importance of loyalty and vigilance in protecting our nations and values.

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