History's Greatest Crime Sprees
History’s Greatest Crime Sprees

History’s Greatest Crime Sprees

Khalid Elhassan - April 15, 2021

History’s Greatest Crime Sprees
River piracy was an ever-present risk to nineteenth-century settlers, like these descending the Ohio River. Clermont County Park District

5. Big Harpe’s Most Depraved Crime Was Against His Own Infant Daughter

The Harpe Brothers were forced to flee to Kentucky, and began a lethal crime spree en route. They killed a peddler and stole his horse and goods, did in two travelers from Maryland, and slew a Virginian. They were pursued and captured but escaped the gallows by breaking out of the state prison in Danville, Kentucky. When a posse was sent after them, the Harpes retaliated by slaughtering a young son of a man who had helped the authorities pursue them. When Kentucky’s governor placed a $300 reward on their heads, the brothers fled northward to Illinois. Along the way, they slew five men.

History’s Greatest Crime Sprees
Cave in Rock, the crime den where the Harpe brothers sheltered with river pirate Samuel Mason and his crew. Wikimedia

The brothers eventually made their way to Cave-In-Rock, a cave in bluffs overlooking the Illinois bank of the Ohio River. It was the stronghold of a ruthless river pirate named Samuel Mason, and the Harpes joined his crew. However, the Harpes’ sadism appalled even cutthroats like river pirates. Among other things, the brothers enjoyed taking captives to the top of the bluff, stripping them naked, and kicking them off. So Mason forced them to leave. They returned to Tennessee and continued piling up the bodies. Among them was Big Harpe’s own infant daughter, whom he killed in August 1799, because her crying annoyed him.

History’s Greatest Crime Sprees
The Harpe brothers. Pinterest

4. The Harpe Brothers’ Violent Spree Ended When Violent Justice Caught Up With Them

In August, 1799, the Harpe Brothers also gutted a man. When the unwary Stegall family gave them shelter in Kentucky, they repaid the hospitality by slaying one of their house guests. In another crime against an infant, they also slew Mrs. Stegall’s four-month-old baby boy, because his crying annoyed them. When a horrified Mrs. Stegall screamed, the Harpe brothers did her in too. Those depravities led to the formation of a posse that included Moses Stegall, whose wife and baby the Harpes had slain. They caught up with the siblings on August 24th, 1799, just as they were about to kill another victim. The brothers tried to flee, but Micajah “Big” Harpe was shot in the leg and back.

While Big Harpe was still conscious, Moses Stegall slowly cut off his head, which was later spiked on a pole. Wiley “Little” Harpe escaped and rejoined Samuel Mason’s river pirate crew. Four years later, the Cave-In-Rock was raided, and Little Harpe escaped with Mason, who was wounded. Harpe, who was using an alias, killed Mason, cut off his head, and along with another escaped pirate, tried to claim a reward. While presenting Mason’s head, Harpe and his companion were recognized as outlaws and arrested. They were tried, convicted, and sentenced to death. The Harpe depravities ended in January, 1804, when Little Harpe was hanged.

Related: America’s First Serial Killers Were Kicked Out of a Pirate Gang For Being Too Violent.

History’s Greatest Crime Sprees
Harold Cole. Imgur

3. The English Jailbird Who Went on a WWII Crime Spree

Career criminal Harold Cole (1906 – 1946) was an English jailbird who served during WWII in the British Army, the French Resistance – and double-crossed both by working for the Germans. Then he betrayed the Germans by working for the Americans at war’s end to hunt down Nazis. During his extraordinary wartime career, which combined espionage with crime, Cole lied and conned his way across France, joined the Nazis, and snitched on the Resistance, resulting in the arrest and execution of many.

By the time he was a teenager, Cole was already a burglar, check forger and embezzler. By 1939, he had served multiple stints behind bars in various prisons. When WWII began, he lied about his criminal history to enlist in the British Army and was sent to France. Promoted to sergeant, he was arrested for stealing money from the Sergeants’ Mess to spend on hookers. He became a POW in May 1940, when the Germans captured the guardhouse where he was jailed.

History’s Greatest Crime Sprees
A disguised Harold Cole. Second World War Blogspot

2. Stealing From the French Resistance

Harold Cole escaped from his German captors, and made his way to Lille, France. There, he got in touch with the French Resistance and falsely claimed that was a British intelligence agent sent to help stranded and escaped British military personnel. For some time, Cole actually did some positive work and escorted escaped personnel across Nazi-occupied territory to the relative safety of Vichy France. From there, the fugitives slipped into neighboring Spain, and secured berths on ships headed to Britain.

However, Cole was unable to shake his shady ways. He went back to the same kind of crime that had got him locked up in a British Army guardhouse, and embezzled from French Resistance, stealing from the funds intended to finance escape operations. Cole used the money to pay for a high society lifestyle of nightclubs, pricey restaurants, expensive champagne, fast cars, and faster girls. When his thefts came to light in 1941, the Resistance arrested and locked him up. While they deliberated what to do about him, Cole escaped.

History’s Greatest Crime Sprees
Harold Cole in disguise. Daily Mail

1. This Crime Bird Betrayed the Resistance by Joining the Nazis, then Betrayed the Nazis by Helping the US Army Hunt Them Down

On the run from the French Resistance, Harold Cole turned himself in to the Germans. He gave them 30 pages of Resistance member names and addresses and became an agent of the SS’ Sicherheitdienst, or SD. In the ensuing roundup, over 150 Resistance members were arrested, of whom at least 50 were executed. Cole was present during the interrogation and torture of many of his former colleagues. When the war turned against the Germans and Allied armies neared Paris in 1944, Cole fled in a Gestapo uniform. In June 1945, he turned up in southern Germany, where he claimed to be a British undercover agent and offered his services to the American occupation forces.

History’s Greatest Crime Sprees
Harold Cole mugshots. Daily Mail

Triple crossing, he turned against the Nazis, hunted and flushed them out of hiding, and murdered at least one of them. The British discovered Cole whereabouts and arrested him, but he escaped his military prison and headed to France. There, French police received a tip revealing his whereabouts in a central Paris apartment. On January 8th, 1946, they crept up a staircase to seize him. However, the cops’ heavy tread gave them away, and Cole met them at the doorway, pistol in hand. He was killed in the ensuing shootout after he was hit multiple times and bled to death.


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

American Weekend, October 23rd, 1998 – Frontier Serial Killers: The Harpes

Bondeson, Jan – Queen Victoria’s Stalker: The Strange Story of the Boy Jones (2012)

Botting, Douglas – The Pirates (1978)

Cracked – 7 ‘Whaaat’ Crimes You Won’t Believe Are True

Daily Mail, June 30th, 2017 – The Worst Traitor of All: How an East End Jailbird Lied and Cheated His Way Across France, Joined the Nazis and Condemned 150 Resistance Fighters to Death

Duggan Christopher – Fascism and the Mafia (1989)

Gigantino, Anthony, La Salle University Digital Commons, The Histories, Volume 4, Issue 1, Article 3 – Il Duce and the Mafia: Mussolini’s Hatred of the Mafia and the American Alliance With Organized Crime

Guardian, The, December 11th, 2003 – Keely’s Trickster Engine

History Collection – Criminal Schemes You Won’t Believe Actually Happened

Legends of America – The Vicious Harpes: First American Serial Killers

Lock Haven University – The Keely Motor Hoax

Murderpedia – Harpe Brothers

Murderpedia – Sada Abe

Murphy, Brendan – Turncoat: The Strange Case of British Sergeant Harold Cole, the Worst Traitor of the War (1987)

Museum of Hoaxes – Keely Motor Company

Republic of Pirates – Stede Bonnet Biography

Smithsonian Magazine, July 31st, 2007 – The Gentleman Pirate

Smithsonian Magazine, June 30th, 2014 – The Amazing (if True) of the Submarine Mechanic Who Blew Himself Up Then Surfaced as a Secret Agent for Queen Victoria

Timeline – This Teen Stalker Stole Queen Victoria’s Panties and Lived in Buckingham Palace Chimneys For a Year

True West Magazine, October 11th, 2016 – October Was Black Bart’s Favorite

Wikipedia – Harpe Brothers

Wikipedia – Sada Abe