7 Most Famous Botched Executions in History

Updated: 4/28/2025

Authorities try to make an official execution as quick and painless as possible – the punishment is the ending of someone’s life, not the method of the killing.

The US Constitution forbids ‘cruel and unusual punishment,’ which is why the Death Penalty is generally carried out by lethal injection in most states these days.

Even with experienced executioners, things can and do go wrong. A lethal injection using new drugs went wrong in 2014, people have taken a lot longer than normal to die in the gas chamber, and all sorts have gone wrong with hangings in years past.

Here are 7 of the most famous botched executions in history!

#1: Joseph Wood Execution (2014)

When European countries banned exporting execution drugs to the U.S., Arizona had to improvise.

Bad idea.

Wood, convicted of double murder, became an unwitting test subject for a new drug cocktail.

Instead of the quick death promised by sodium thiopental, Wood spent nearly 40 minutes gasping and writhing on the gurney—like a fish out of water, but with much higher stakes.

When they couldn’t get it from there, Arizona tried a combination of midazolam and hydromorphone, which led to his death.

This DIY chemistry experiment proved that sometimes, alternative medicine isn’t the answer.

#2: Barzan Ibrahim al Tikriti Execution (2007)

Following Saddam Hussein’s execution, his half-brother Barzan Ibrahim (convicted of murdering 148 Shiite Muslims) was next in line for the gallows. The executioner, apparently not a measuring tape enthusiast, miscalculated the rope length needed.

When Ibrahim dropped through the trapdoor, physics took over with gruesome efficiency.

Instead of breaking his neck, the force completely separated his head from his body—turning what should have been a solemn punishment into a medieval spectacle that nobody had signed up to see.

#3: Donald Eugene Harding Execution (1992)

After Arizona dusted off its death penalty following an 18-year break, double murderer Donald Harding became their first “customer.”

The gas chamber was supposed to provide a quick death by cyanide-induced asphyxiation.

Instead, witnesses watched in horror as Harding gasped, screamed, and thrashed for nearly 11 minutes, even smashing his head against a steel pole.

Officials later claimed he was already brain-dead during the pole-smashing phase—a strange comfort to those who had to watch the whole ordeal.

#4: Pedro Medina Execution (1997)

The electric chair was invented with the belief that it would cause a humane, painless death. The truth, however, was far from that.

Even with a very powerful current passing through the body from the leg to the head, it often took a great deal of time to stop the heart from beating.

In 1997, murderer Pedro Medina was sent to the Electric Chair in Florida. Witnesses gasped when they witness actual flames fly from the top of Medina’s head and reported the smell of burning flesh as the current passed through his body.

When the flames came out of his head, the executioner stopped the current, but Medina was dead a minute or two later.

Investigators said that the sponge that was put on his head to conduct the current wasn’t wet enough at the time of the execution.

#5: Joachim von Ribbentrop Execution (1946)

Following the end of World War II, 10 high-ranking Nazi officials were sent to the gallows at the request of the Allies, who had tried them at the famous Nuremberg Trials.

The hangman got his calculations wrong with a number of Nazis. The Nazi Foreign Minister Joachim von Ribbentrop ended up spending 15 minutes at the end of the rope, slowly being strangled to death.

The head of the German Luftwaffe, Hermann Goering, who gave orders to bomb millions of innocent people in cities all over Europe during the war, managed to escape his own death by hanging.

How?

Goering concealed a glass vial of cyanide, and the morning he was due to hang, he took it out and bit into it, killing himself before the hangman could do it.

#6: George Painter Execution (1891)

In 1891, George Painter was sentenced to death for murdering his girlfriend. He protested his innocence until the day he was due to die.

Painter was allowed to say his last words before being led onto the scaffold. The executioners tied his legs together and put a hood over his head before the noose was lowered around his neck.

When they pulled the lever to the trapdoor, his body fell straight through and snapped the rope that was meant to kill him.

This must have burst a blood vessel because as they were carrying him up to be hanged again, blood spurted everywhere.

Thankfully, the second hanging was successful.

#7: Lady Margaret Pole Execution (1541)

In 1541, Lady Margaret Pole was sentenced to be beheaded at the command of King Henry VIII in England. She committed no crime, but her son had refused to accept that the King’s marriage to Anne Boleyn was legal.

He had escaped to France, so the King’s men couldn’t get to him and got his Mum instead.

The executioner was inexperienced, and Lady Pole was in no mood to cooperate.

The story goes that she had to have her head forced onto the block and the ax man missed several times, slashing her shoulder and cutting off part of her head before finally taking her head off.

Wrapping it Up

These seven botched executions show us a simple truth – there’s no perfect way to execute someone.

From Wood’s 40-minute struggle to Lady Pole’s brutal beheading, these cases span hundreds of years but share the same problem: what’s meant to be quick and painless becomes anything but.

It’s strange that we try so hard to make killing painless. We want death to be quick but certain, just but merciful. These execution failures remind us that even when we try to make death “clean,” it rarely cooperates.

As we argue about the death penalty today, these grim stories make us wonder: if we can’t guarantee a quick and painless death, should we be in the business of execution at all?