History’s Biggest Villains Who Got Exactly What Was Coming to Them
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Some people go through life doing genuinely terrible things and somehow manage to die peacefully in their sleep. It’s infuriating. But history, at its most satisfying, occasionally dishes out consequences that fit the crime with almost poetic precision. Some of these stories have featured on UtterlyInteresting.com before, others are new additions to the rogues' gallery but they all deserve to be included
This list features some of the most spectacularly awful human beings who ever lived, and the deeply satisfying ways the universe eventually settled its accounts with them. No dashes. No mercy.
1. Leopold and Loeb: The ‘Superior Intellects’ Who Weren’t
In 1924, Nathan Leopold and Richard Loeb were wealthy University of Chicago students and lovers who had convinced themselves their towering intellects placed them above the law. To prove it, they committed petty crimes for sport, then escalated: they kidnapped and murdered 14-year-old Bobby Franks, a distant cousin of Loeb’s, not for money or revenge but simply to demonstrate they could get away with it. After the killing, they went for root beer and hot dogs.
They were quickly caught, not because detectives were particularly clever but because Leopold left his custom eyeglasses at the crime scene. All that superior intellect, and it cost them a pair of spectacles. Famed attorney Clarence Darrow saved them from the electric chair and they were sentenced to life plus 99 years.
Loeb’s karmic reckoning arrived in 1936 when a fellow inmate named James Day attacked him in a prison shower, slashing him more than 50 times with a straight razor. The man who believed himself intellectually superior to everyone around him was killed by someone he looked down on. Leopold, frustratingly, was paroled in 1958 and lived another 13 years. Some karma takes longer to arrive.
You can read the full story of these two in the Utterly Interesting article on Leopold and Loeb
2. Sigurd the Mighty: Killed by a Dead Man’s Tooth
Sigurd the Mighty was a Viking Earl who conquered much of northern Scotland in the 9th century, leaving a trail of destruction across the land. After defeating a Scottish chieftain named Máel Brigte in battle, Sigurd beheaded him and tied the severed head to his saddle as a trophy, because Vikings weren’t subtle.
As he rode home in triumph, the dead man’s teeth grazed Sigurd’s leg. The wound became infected and Sigurd died shortly after. He was killed by a corpse he’d already defeated. History rarely gets more poetic than that.
3. Andrew Myrick: The Man Who Said Let Them Eat Grass
In the summer of 1862, Andrew Myrick was a trader at the Lower Sioux Agency in Minnesota when the Dakota people, starving after being forced onto reservations and denied treaty payments and food shipments, came to him for help. His response was as cruel as it was memorable. When asked what the starving people should eat, he reportedly sneered that they could eat grass or their own dung.
Days later, the Dakota rose up in what became known as the Dakota War of 1862. On the very first day of the uprising, Myrick was killed. When his body was found, the Dakota had stuffed his mouth with grass. History may not always remember the names of the cruel, but it occasionally gives them a fitting last line.
4. Michael Anderson Godwin: Escaped the Chair, Not the Toilet
In 1983, Michael Anderson Godwin was convicted of murder and sentenced to death by electric chair in South Carolina. His conviction was later overturned on appeal and he received a life sentence instead. A lucky break, you might think.
Six years later, Godwin was sitting naked on the metal toilet in his prison cell, attempting to repair a pair of earphones connected to his television. He bit into a live wire. He electrocuted himself on the toilet. The man who escaped the electric chair was killed by the electric toilet. There’s really nothing to add.
5. George Beurling: The Ace Who Flew Too Close to His Own Ego
George Beurling was Canada’s most celebrated fighter pilot of World War II, with 31 confirmed kills and a nickname – “Buzz” – earned from his habit of flying dangerously low over airfields to show off. He was genuinely brilliant in the air and completely insufferable on the ground, insulting fellow pilots, flouting regulations, refusing to fly in formation and generally making himself impossible to work with.
After the war, no air force wanted him. Not Canada’s, not Britain’s. He eventually took a contract flying for the newly forming Israeli Air Force and died in 1948 when his plane exploded on takeoff during a test flight in Rome. He was 26. Whether it was sabotage, mechanical failure, or one final ill-judged bit of showboating, the pilot who thought he was above the rules died far from home with nothing left to prove.
You can read more about George Beurling and his escapades in the Utterly Interesting article here
6. Thomas Midgley Jr.: Inventor of Two Environmental Catastrophes, Killed by His Own Machine
Thomas Midgley Jr. helped General Motors develop leaded petrol in the 1920s. Workers promptly began dying of lead poisoning. Rather than back down, Midgley staged a now-legendary press conference in which he poured leaded fuel over his hands and held it to his face to demonstrate it was safe. He was quietly removed from work shortly afterwards to recover from lead poisoning.
He also helped introduce CFC refrigerants, later found to be destroying the ozone layer. Two inventions, two global disasters.
In 1940, Midgley contracted polio and designed an elaborate rope-and-pulley system above his bed to help him move. In 1944, he became entangled in the device and accidentally strangled himself to death. The man whose inventions may have harmed more people than almost anyone in history was ultimately killed by one of his own.
7. Robespierre: The Guillotine Finally Came for Its Most Devoted User
Maximilien Robespierre didn’t start out as a monster. In the early days of the French Revolution he argued for the abolition of slavery, universal suffrage, and the end of the death penalty. Then he discovered how useful the guillotine was for silencing enemies and never looked back.
During the Reign of Terror, Robespierre signed off on the executions of thousands: nobles, political rivals, ordinary citizens who seemed insufficiently enthusiastic about the revolution. He came to believe he alone could determine who was virtuous enough to survive in the new France.
By July 1794, his own allies were terrified they’d be next. They staged a coup, and Robespierre was taken to the very same guillotine he’d used to purify France. The man who sent thousands to their death by guillotine was guillotined by the people he’d inspired. The revolution ate its own.
8. Marcus Crassus: The Richest Man in Rome Died Choking on Gold
Marcus Crassus was the wealthiest man in the Roman Republic, having made his fortune through silver mines, slave-labour fire brigades (he’d let your house burn until you sold it to him at a knock-down price), and entire districts of Rome. His greed was so legendary it’s still a byword for avarice.
Unsatisfied with mere obscene wealth, Crassus wanted military glory to match the reputations of Caesar and Pompey. In 53 BCE he launched an invasion of Parthia (roughly modern Iran) with no clear strategy and a spectacular underestimation of the enemy cavalry. His army was massacred at the Battle of Carrhae. Crassus tried to negotiate surrender and was captured.
Ancient writers record that the Parthians, mocking his insatiable hunger for gold, poured molten gold down his throat so he could “finally have his fill.” Historians note this may be propaganda rather than literal fact, but the story has stuck for 2,000 years because it feels exactly right.
9. Pope John XII: The Pontiff Who Apparently Died Mid-Sin
Pope John XII became pope at around 18 years of age and spent much of his pontificate making a spectacular mockery of the office. Medieval sources, some hostile and some extremely colourful, accused him of turning the Lateran Palace into something closer to a brothel, drinking toasts to the devil, ordaining a deacon in a horse stable, and invoking pagan gods while gambling. His court was so scandalous that Holy Roman Emperor Otto I convened a synod to deal with him.
He was deposed in 963 CE, reinstated, and died in 964 CE at around 27 years old. The most persistently repeated account of his death holds that he died of a stroke while in bed with a married woman, though some sources suggest the woman’s husband may have had a direct hand in the matter. Whatever the precise truth, the man who turned the papacy into a personal pleasure palace managed to exit it in equally scandalous fashion. You can read the full story on the
10. Ken McElroy: The Town Bully Nobody Saw Shoot
Ken McElroy terrorised the small town of Skidmore, Missouri for years. He was accused of assault, arson, child molestation, and murder, yet managed to avoid conviction through witness intimidation and legal delays. He was tried dozens of times. Nothing stuck. In 1981 he was finally convicted of shooting a 70-year-old grocer named Bo Bowenkamp over a disputed piece of candy and was out on bail pending appeal.
On 10 July 1981, with roughly 60 townspeople gathered in the main street, Ken McElroy was shot dead in his truck. Two weapons were fired. Forty to sixty people were present. Nobody saw a thing. Not one person in that town of 400 was willing to name a shooter, and no one was ever charged. Sometimes the justice system fails and a community does its own accounting. You can find the full story in the Utterly Interesting piece on Ken McElroy.
11. Lavrentiy Beria: Stalin’s Monster Outlived His Protector by Less Than a Year
Lavrentiy Beria ran Stalin’s secret police, the NKVD, and is widely considered one of the most sadistic figures in Soviet history. He personally oversaw mass executions, signed off on torture as standard procedure, and has been credibly accused of serial sexual violence against women and girls picked up off the streets of Moscow by his security detail. Stalin himself reportedly told his daughter to avoid Beria.
When Stalin died in March 1953, Beria made his move for power. He positioned himself as a reformer, freed some political prisoners, and began manoeuvring to take the top job. His Politburo colleagues moved faster. Within months he was arrested, accused of treason and espionage, and shot. The man who had ordered the deaths of hundreds of thousands of people was executed in a basement in December 1953, reportedly begging for his life.
Read more in the Utterly Interesting article on Lavrentiy Beria.
12. Irma Grese: The “Beautiful Beast” of Auschwitz
Irma Grese was one of the most feared guards in the Nazi concentration camp system, serving at both Auschwitz and Bergen-Belsen. She was 19 when she began her service and quickly developed a reputation for sadistic cruelty, selecting prisoners for the gas chambers, beating inmates with a plaited whip she carried everywhere, and having dogs set on people for entertainment. She was known, with grim irony, as the “Beautiful Beast.”
Captured by British forces after the liberation of Bergen-Belsen, she was tried at the Belsen Trial in 1945 alongside other camp staff. She was found guilty of crimes against humanity, showed no remorse in court, and was hanged on 13 December 1945 at the age of 22. She was the youngest woman executed under British jurisdiction in the 20th century. The full story is covered in the
13. Oskar Dirlewanger: Too Brutal Even for the SS
Oskar Dirlewanger managed the remarkable feat of being considered too violent and unstable even by the standards of the SS. A convicted child molester who somehow secured a command through connections to Heinrich Himmler, he led the Dirlewanger Brigade, a unit staffed largely by convicted criminals, through some of the most horrific atrocities of the Second World War. The unit was responsible for massacres across the Eastern Front and played a central role in the catastrophic suppression of the Warsaw Uprising in 1944, during which tens of thousands of civilians were murdered.
Dirlewanger was captured by French forces after the German defeat and, depending on which account you believe, was either beaten to death by Polish guards in custody or died from injuries inflicted during his interrogation in June 1945. He never faced a formal trial. The full, deeply unpleasant story features in the Utterly Interesting piece on Oskar Dirlewanger.
14. Charles Ponzi: Died Penniless After Promising Everyone Easy Riches
In 1920, Charles Ponzi promised Boston investors a 50% return in 45 days by trading international postage coupons. It was sophisticated enough that people nodded and handed over their savings without asking too many questions. He never invested any of it. He simply paid early investors with money from new ones and pocketed the difference, buying a mansion, hiring servants, and strutting around Boston like a financial genius.
When the scheme collapsed, Ponzi was arrested, served time, was released, ran another scam, was arrested again, and was eventually deported to Italy. He spent his final years working as a low-paid hospital clerk, in failing health, barely able to cover his bills. The man who promised the world died with virtually nothing, which is exactly what his victims were left with.
Sources
1. Smithsonian Magazine – The Leopold and Loeb “Crime of the Century”: https://www.smithsonianmag.com/history/the-crime-of-the-century-a-century-later-180984586/
2. The Orkneyinga Saga (medieval Icelandic source on Sigurd the Mighty)
3. Minnesota Historical Society – Andrew Myrick and the Dakota War of 1862: https://www3.mnhs.org/usdakotawar/stories/history/andrew-myrick
4. Los Angeles Times – Michael Anderson Godwin electrocution, 1989: https://www.latimes.com/archives/la-xpm-1989-03-08-mn-277-story.html
5. Canada Eh X – George Beurling: https://canadaehx.com/2022/07/18/george-beurling/
6. NPR / Smithsonian Magazine – Thomas Midgley Jr.: https://www.npr.org/2013/04/18/177046258/the-man-who-tried-to-clean-up-the-world
7. Britannica – Maximilien Robespierre: https://www.britannica.com/biography/Maximilien-Robespierre
8. Britannica – Marcus Crassus: https://www.britannica.com/biography/Marcus-Licinius-Crassus
9. UtterlyInteresting – The Depraved Life of Pope John XII: https://www.utterlyinteresting.com/post/the-depraved-life-of-pope-john-xii-history-s-most-scandalous-pontiff
10. UtterlyInteresting – Ken McElroy, The Town Bully: https://www.utterlyinteresting.com/post/ken-mcelroy-the-town-bully-murdered-in-front-of-a-crowd-of-witnesses-but-nobody-saw-a-thing
