Cautionary Tales with Tim Harford - Derek Bentley Must Hang

Episode Date: October 24, 2025

An amateurish burglary in 1950s London ends in murder. One of the men involved is a 19-year-old named Derek Bentley. Bentley has the understanding of a child - and he wasn't the killer. But the British justice system seems determined to deliver the death penalty. The fate of capital punishment lies in the balance, and so too does the fate of Derek Bentley. For a full list of show notes go to timharford.com, and to join our new Patreon, go to patreon.com/cautionaryclub. See omnystudio.com/listener for privacy information.

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Call 844-844-I-Hart. I'm Jonathan Goldstein, and on the new season of heavyweight. And so I pointed the gun at him and said this isn't a joke. A man who robbed a bank when he was, 14 years old. And a centenarian rediscovers a love lost 80 years ago. How can a 101-year-old woman fall in love again? Listen to heavyweight wherever you get your podcasts.

Derek Bentley towered over the guards pacing beside him in the exercise yard of London's Wandsworth Prison. Derek was broader than his warders too. He was a physically imposing 19-year-old with a look of a weightlifter or a boxer. The prisoner's shock of yellow hair, worn long and combed back as was the teen fashion in 1953,

danced in the cold winter breeze. Occasionally, smoke from a cigarette would blow back into Derek's eyes, making him wince. But despite his bulk, a visitor to the jail, looking down at the scene and carefully sizing Bentley up, saw something childlike in the convict. In his grey prison clothes, he looked like a schoolboy dressed with some classroom charade. the prison doctors agreed since his arrest the previous November they'd subjected Derek to a battery of tests

the results revealed a low IQ a dearth of literacy skills and the developmental age not of 19 but more like that of a child of 11 or 12 the prisoner was deemed to be in the parlance of the time borderline feeble-minded In truth, there were many things that Derek Bentley didn't understand.

But the most pressing was why he was in prison awaiting execution. He had broken into a warehouse. And during the course of that crime, a policeman had been shot dead. But Derek hadn't held the gun and was already under arrest when the fatal shot rang out. The murderer, a 16-year-old named Christopher Craig, had been found guilty of the actual killing. But he wasn't going to hang. It all confused Derek Bentley.

Why was he the one to die? Derek's family didn't think he should hang either. The trial jury had asked for the death penalty not to be imposed, so there seemed to be hoped that the authorities would heed this appeal for clemency. Indeed, so certain were the Bentleys that he'd be freed, they'd wrapped Christmas presents for Derek, a tie and a box of chocolates, and placed them under the family tree. You can open them when you get home, was the implication.

But as December gave way to January, and the date of his execution drew near, the man who held Derek's fate in his hands, Home Secretary David Maxwell Fife was in no mood to show leniency. A petition by more than 200 members of Parliament plus protests outside Downing Street and government offices and finally Maxwell Fife's own home

hadn't yet prompted the Cabinet Minister to change his mind. On the evening before his son's scheduled execution, William Bentley led that noisy round, outside the politician's smart London apartment. Bentley is not sleeping tonight, said William of his boy. And neither shall Maxwell fight. The newspapers and radio were a buzz with these last-minute moves. Political leaders, among the men who'd held senior legal positions,

beseeched Her Majesty the Queen to intervene in a case that was, they said, Out of accord with natural justice. So, at one minute to nine, on the morning of January the 28th, when a well-dressed man burst into the condemned cell, Derek Bentley assumed that this was legal counsel bringing word of a reprieve. Derek stood to receive the good news. The two prison officers, who were his constant shadow, rose to. Then, Derek noticed something peculiar.

In the stranger's hands was a loop of yellow leather. Swiftly, this was passed over Derek's wrists, binding them tightly behind his back. The man in the suit was no lawyer. This was Albert Pierpoint, England's chief hangman. If there was to be a reprieve, it had better happen soon. I'm Tim Harford, and you're listening to another cautionary tale. Let's go back three months to November 2nd, 1952. It's Sunday evening, and darkness has fallen on a cold and drizzly day.

Wiser Britons would seek to be safe beside a fire on such a night, but that wasn't the sort of evening Derek Bentley had in mind. Instead, he was out with his friend Christopher Craig, a 16-year-old whom Derek called kid, or kiddo. By rights, Derek shouldn't have been hanging around with the younger boy. At his age, he should have been conscripted into the military, but the authorities took one look at Derek and decided he was too mentally substandard

to complete compulsory service. Despite his size, Derek was always thought by his teachers to be sheep-like and, Timid. When truancy and petty crime landed him in reform school, it was noted that his lack of intelligence prevents him from joining in many of the indoor games, and he is by no means a sportsman. When tested, Derek's low IQ placed him in the bottom 1% of the population. Today, someone like Derek would be said to have special needs, and and would, we'd hope, have those needs met.

But the language used to describe Derek back then was brutal, and sympathy for him limited. One expert pleaded that he be sent as far away from home as possible to a school for sub-normals. Derek, who also suffered fits and seizures, fared little better in the world of work. He took a job moving furniture, but his back gave out. A career as a garbage collector was also brief.

Within weeks, he was demoted to sweeping the streets and then fired altogether. Mocked, rejected and belittled, the team then retreated to the security of the Bentley family home. But on this dank November Sunday evening, Derek ventured away from the warmth of the hearth to catch a bus that would take him on a terrible misadventure. His choice of companion was his first mistake of that evening.

Christopher Craig had ambitions to be a gangster. His older brother, Niven, had just begun a 12-year prison sentence for a shocking armed home invasion. Christopher had angrily watched his brother be convicted, and learned a lesson. But it was not that crime doesn't pay. Instead, he decided that you shouldn't ever let yourself be caught. Still seething with resentment, Christopher hopped onto that southbound bus,

carrying a 45 revolver in his pocket. A relic of World War I, the pistol's barrel had been shortened to make it easier to conceal. Its power and accuracy were further. reduced because Christopher had struggled to find the right ammunition. Several of the cartridges were intended for a smaller gun. Still, the weight of the firearm in his pocket no doubt pleased Christopher, making him feel like the Hollywood gangster of his fantasies.

And he'd need that swagger for the job he had in mind. The younger boy had dared Derek to join him breaking into a local butcher shop. Derek was already carrying a small knife but as their bus chugged towards their target Christopher gave his friend a fearsome knuckle-duster too the robbery was a bust somebody was in the butcher shop but Christopher spotted a new opportunity

the nearby warehouse of a candy company Christopher scaled its gate hoping to break in via the roof Derek trailed behind, but they've been spotted. Constables from the nearby police station quickly had them surrounded. Perhaps more athletic than his colleagues, Detective Constable Fred Fairfax was the first to climb the roof via a drain pipe. In the gloom, he saw the boys scurry into hiding

and called on them to surrender. If you want us, fuck you will come and get us! replied Christopher. Perhaps enraged by such impertinence, the constable rushed the burglars and grabbed hold of Derek before the youth broke free. It's here that eyewitness accounts differ. Derek denied shouting anything,

a version of events backed by Christopher. The other policeman heard nothing, or thought the shout came at a slightly different moment, but Fairfax was certain, as he tussled with a hulking 19-year-old Derek yelled, Let him have it, Chris. But was Derek simply pleading for his partner in crime

to surrender the pistol he was now brandishing? Let him have it, Chris! Or was Derek channeling his inner James Cagney and growling for his friend to open fire? Let him have it, Chris! Christopher's opening shot hit ferns, Fairfax, grazing his upper arm. Undaunted, the officer grabbed Derek again and used the boy as a shield while he ran for cover. As more officers closed in, Christopher continued his fusillade. He also kept up a barrage of taunts.

Come on, you brave coppers. Think of your wife. I am Craig. You just given my brother 12 years. Come on, you coppers. I'm only 16. Two of these coppers had made it into the warehouse and were taking the stairs up to a door leading to the roof. Police constable Sidney Miles kicked it open and burst out into the night. A bullet struck him between the eyes,

killing him instantly. Cautionary tales returns in a moment. Run a business and not thinking about podcasting, think again. More Americans listen to podcasts than ad-supported streaming music from Spotify and Pandora. And as the number one podcaster, IHeart's twice as large as the next two combined. So whatever your customers listen to, they'll hear your message. Plus, only I-Heart can extend your message to audiences across broadcast radio. Think podcasting can help your business.

Think I-Hart, streaming, radio, and podcasting. Call 844-8-4-Eheart to get started. That's 844-8-4-Eyheart. I'm Jonathan Goldstein, and on the new season of heavyweight... And so I pointed the gun at him and said, this isn't a joke. A man who robbed a bank when he was 14 years old. And a centenarian rediscovers a love lost 80 years ago. How can a 101-year-old woman fall in love again?

Listen to heavyweight wherever you get your podcasts. There was widespread revulsion at the murder of Sydney Miles. This is not England, said the vicar at Sydney's funeral. The England, for which men and women have laid down. their lives. Sidney's coffin was topped by his police helmet and a wreath from his wife. Officers from across the country were there, senior officials too, including the man ultimately responsible for law and order, the Home Secretary, David Maxwell Fife.

The shooting on that warehouse roof unnerved the nation, partly because it was so unusual. The number of times a year guns were fired in London robberies, you could count them on the fingers of one hand. And yes, the murder rate was rising, but from its lowest point for centuries. After his initial attempt to flee, Derek Bentley had meekly stood with the police, seemingly accepting his detention.

But Christopher Craig had continued to exchange shots with armed police until his supply of ammunition exhausted he'd flung himself from the rooftop. Though badly injured, he survived the fall, unrepentantly telling the arresting officers, I wish I'd kill the fucking lot. Given such violence and such brazenness, It's little wonder that some people wanted to see an example made of these teen criminals.

The topic even came up when Sir Charles Hardy, one of the most famous businessman of the day, lunched with a certain Baron Goddard, the uncompromising Goddard who basked in the nickname the Tiger, told his dining companion that Bentley and Craig had to be found guilty at all costs. Such of you might not seem so remarkable, given public anger in 1952, only Goddard was the Lord Chief Justice of England, the most senior judge in the land,

and he'd just appointed himself to oversee the trial. William Edgar Raynor Goddard, seems to have been a lifelong fan of the hangman. As a pupil at one of England's most exclusive private schools, he was said to recite, word for word, the death penalty. The sentence of the court is that you be taken from this place to a lawful prison and thence to a place of execution. It was said to be Goddard's party piece,

preferred to telling a joke or singing a song. And that you may be hanged by the neck until you be dead. And may the Lord have mercy on your soul. As an adult, he remained an enthusiastic supporter of violent punishments, meeting out whippings and beatings for lesser offences and hangings for more serious crimes. However, his elevation to the highest level of the judiciary came at a time that such views were being challenged.

Following World War II, an election swept the anti-hanging Labour Party into power. And many of the new socialist politicians taking their seats in the House of Commons were young servicemen returning from war, sick perhaps of violence. These elected politicians voted to end hanging, only for the unelected lords in the upper chamber where Baron Goddard sat, to overrule them. This sparked a constitutional crisis. The lords weren't supposed to defy the commons. But a compromise was reached. A special commission would thoroughly review how the death penalty was administered, so thoroughly, in fact, that the report would take four whole years to complete.

So hanging was reprieved, much to Goddard's delight. He threatened to resign as Lord Chief Justice whenever the repeal of the death penalty looked imminent. But with the political tide clearly shifting against execution, Goddard thought it was time for the justices beneath him to hand down death sentences whenever possible. I advise all judges to harden their heart. The joint trial of Derek Bentley and Christopher Craig

took place at the central criminal court, London's famous Old Bailey. The prosecution case against 16-year-old Christopher was clear. He'd fired the fatal shot. But Derek, it was argued, was also a murderer because he'd known Christopher was armed, and furthermore had verbally encouraged him to open fire. Derek denied knowing anything about the pistol until it was drawn on Detective Fairfax, but the jury was told this version of events was...

Almost inconceivable. I should think you would come to the conclusion that the first thing, almost, Craig would tell him, if they were going on a shop-breaking expedition, was, it's all right, I've got a revolver with me. This bold statement, not backed up by any evidence, was made not by the prosecutor, no, but by the judge, Tiger Goddard. From the outset, the 75-year-old in his red robes and ceremonial wig

seems to have made good on his pledge that the pair would be found guilty at all costs. A judge's role at trial is complex. But the bedrock of their duty is to explain to jurors that the onus is on the prosecution to prove its case beyond reasonable doubt. But at Derek Bentley's trial, Goddard didn't bother to explain what reasonable doubt meant. He did mention that it was for the prosecution to make their case and not for the defendants to prove their innocence,

but he did so in a single sentence, adding grumpily that he considered that such a reminder was hardly necessary. But don't be fooled into thinking Goddard wasn't keen to address the 12 men in the jury box. He was. With both defendants denying that Derek had said, Let him have it, Chris, the jury only had the slightly confused testimony of the police witnesses to go on.

Instead of pointing out that police officers don't have some special status as accurate and reliable witnesses, Goddard drew a direct link between the gallantry and resolution of the constables on the rooftop that night and their evidence to the court. They were conspicuously brave. Are you going to say they are conspicuous liars? That's quite something for a judge to tell a judge. jury. Given public outrage about the murder of a police constable, Goddard's other duty was to tamp down emotions in his courtroom and encourage the jurors to weigh the facts as presented and not let any personal prejudices or feelings of disgust or anger cloud their decisions. But instead, Goddard indulged in courtroom theatrics of the most stunning kind. At one point, he asked for the weapons found on Derek Bentley to be passed to him.

Where is that knuckle duster? Have you ever seen a more horrible sort of weapon? You grasp it here. Your fingers go through. I cannot quite get mine through. And you've got a dreadful, heavy steel bar to strike anybody with. And you can kill a person with this, of course. It is a shocking weapon. Goddard then held aloft a small knife taken from Bentley, which he emotively referred to as a dagger. What is he carrying that with him for?

Goddard didn't answer his own question. Perhaps because one plausible response is that Derek Bentley had absolutely no plans to use the weapons. Derek was being tried as an accessory in joint enterprise. It's clear that he was in a joint enterprise with his younger friend to rob the warehouse. He'd scaled a gate and climbed atop the roof. Once discovered by Detective Fairfax, Derek had tried to run away, arguably in a joint enterprise to evade

arrest, but then quickly gave up that effort. Was the joint enterprise now at an end? Long before the murder of Constable Miles? Though armed with a knife and knuckle duster, Derek made no attempt to assault the policeman holding him. And as Christopher Craig kept up his angry, foul-mouth taunting of the police, Derek stood meekly and quietly, occasionally expressing concern for the officer's safety. You want to look out. He'll blow your heads off.

When Fairfax left his prisoner's side for a moment Derek made no fresh attempt to bolt or rejoin his armed comrade if indeed Derek had said let him have it Chris for those words to have earned him a guilty verdict it wouldn't have mattered how they sounded to the teen gunman nor to the police

only that Derek had intended them as an incitement to open fire but Derek's demeanour during his detainment was passive and acquiescent. The teen, described as timid and sheep-like all his life, and with no history of violence, might easily have meant for Christopher Craig to surrender his pistol and accept his lawful arrest.

It's certainly a possibility the jurors should have considered. Just before the jury retired to consider their verdict, Goddard, having praised the prosecution case fulsomely, mocked the defendant. Bentley's defence is, I didn't know he had a gun, and I deny that I said, Let him have it, Chris. I never knew he was going to shoot, and I didn't think he would. The jurymen filed out to begin deliberations, ringing in their ears, an exhortation from highest judge in the land that they should use their common sense.

They took just 75 minutes to find both defendants guilty. Christopher Craig wouldn't hang. He was too young. And since there was a precedent that if a killer didn't hang, an accomplice wouldn't either, the jury asked that Derek's life be spared too. Goddard ignored their plea and recited the death penalty he'd first memorized at school. The sentence of the court

Derek would hang by the neck until dead. And may the Lord have mercy on your soul. The Lord Chief Justice had told his fellow judges that it wasn't their job to show pity to the prisoners in their dock. Four, said Goddard,

in other and higher hands, mercy may be. extended. So, the Lord Chief Justice, having passed a death sentence, sat down to write a letter to a higher hand. The Home Secretary, David Maxwell Fife, the only man who could now save Derek from the hangman's noose. Cautionary tales will be back after the break. Run a business and not thinking about podcasting, think again. More Americans listen to podcasts than ad-supported streaming music from Spotify and Pandora. And as the number one podcaster, IHeart's twice as large as the next two combined.

So whatever your customers listen to, they'll hear your message. Plus, only IHeart can extend your message to audiences across broadcast radio. Think podcasting can help your business. Think IHeart. Streaming, radio, and podcasting. Call 844-844-I-Hart to get started. That's 844-844-Eyehart. I'm Jonathan Goldstein, and on the new season of heavyweight...

And so I pointed the gun at him and said this isn't a joke. A man who robbed a bank when he was 14 years old. And a centenarian rediscovers a love lost 80 years ago. How can a 101-year-old woman fall in love again? Listen to heavyweight wherever you get your podcasts. In the early morning A crowd stood at the gates of Wandsworth Prison,

wrapped up against the cold, they sang hymns and recited psalms. There still seemed hope for Derek Bentley. even inside the prison where he was making his final macabre preparations and calculations hangman Albert Pierpoint wasn't sure his services would be required after all the possibility of a last-minute reprieve still hung in the air stronger than I have ever known it at the very heart of government there was in fact a mood to show mercy The most senior officials in the Home Office advised David Maxwell Fife

to intervene to spare Derek's life. But the Home Secretary was taking his advice from Baron Goddard. I could find no mitigating circumstances in Bentley's case. I am convinced that he is a most dangerous criminal. In his own verdict on the case, which he called a very bad murder. Maxwell Fife said it would be dangerous to let Derek live

since that might encourage similar attacks on unarmed police. Given public anxiety about violent crime, he decreed that Derek must hang. At 8.59 a.m., in the condemned cell, Pierpoint was now standing so close to Derek Bentley that he could talk to the boy in a whisper. Just follow me, lad.

It's all right, Derek. Just follow me. Pierpoint had conducted hundreds of executions and found that moving quietly and calmly but at speed encouraged compliance from the condemned. He feared that if Derek resisted, the powerfully built team could cause havoc.

But sheep-like to the end, Derek meekly followed Pierpoint into the adjoining execution chamber. The guards didn't even have to guide him. Derek helpfully stood on chalk marks, drawn on the wooden trap door, as Pierpoint gently placed, first a white hood and then a noose over the boy's head. The executioner stepped. over to a lever that opened the doors beneath Derek's feet. An assistant was tying the boy's legs together.

When he was done, he gave peer point the agreed signal. The crowd booed as a prison official came out to post two notices. One declared that Derek's execution had taken place before witnesses. The other certified that a surgeon had examined the body and deemed life to be extinct. The two pieces of paper were pinned inside a glazed display case, which someone in the crowd promptly smashed.

I've murdered an innocent boy! cried one protester, as others pelted prison officers and policemen with coins, It's murder, it's murder, it's murder, it's murder, it's murder, it's murder, it's murder, it's murder, it's murder, it's murder, it's murder. So, just 87 days after the shot that killed police constable Miles, Derek Bentley too, was dead. The Bentley family, anything but meek or timid, fought on, demanding a posthumous pardon. When Derek's parents died, his sister Iris devoted herself to the cause.

I'm not the sort of person who gives in. I'll never, never give up. When I die, I want that piece of paper, that pardon, put with me in my coffin. Iris was buried in 1998, but without Derek's pardon beside her. Cruelly, a ruling by the Court of Appeal was not far off. Few people had previously had the courage to contradict Goddard, even after his death in 1971. But the appeal judge was shocked by his handling of Derek's case. He concluded that the Lord Chief Justice had not only denied Derek a fair trial,

but had done all he could to push him. the jury to convict. Overturning that conviction, the appeal judge said, it must be a matter of profound and continuing regret that this mistrial occurred and that the defects we have found were not recognised at the time. Derek Bentley's remaining family rejoiced.

And so did Christopher Craig. The gunman on that awful night in 19, In 1952, served 10 years in prison, and then rehabilitated, lived a quiet, law-abiding life. A day does not go by when I do not think about Derek. Said a now, middle-aged Christopher Craig. Everybody knew that if a policeman dies, somebody has to pay for it. I couldn't. I was underage, and Derek Bentley fitted the bill.

so I had Goddard behaved so abominably and departed so far from the norms of the courtroom to send hapless Derek to his death an obvious answer was that Goddard wielded immense power whilst also possessing a bullish and bullying personality he never doubted his own judgment nor did he tolerate others questioning him That is an awful combination.

Others have claimed that Goddard's obsession with violent physical punishments had a dark, perverse, even sexual bent. Having teenage boys beaten or hanged gave him pleasure. But one must consider a further motive. At a time when abolition seemed close, Goddard pushed so far. fervently, so obscenely for Derek's death in a desperate bid to save hanging. If Lord Chief Justice Goddard and Home Secretary David Maxwell Fife

had hoped the killing of the 19-year-old would bolster the popularity of capital punishment and stave off calls for its abolition, and they were wrong. Nearly 3,000 angry telegrams had arrived at Maxwell Fife's office. and the switchboard had been inundated with telephone calls, many ordinary people were clearly appalled by the hanging. Abolitionists noted this public unease, and Derek's death was cited as a prime reason why capital punishment should now cease altogether.

I am certain that the execution of that youngster was more like murder than anything Derek Bentley did himself. said one campaigning politician. It is absolutely indefensible. In the wake of Derek's death and reacting to public anger, the government changed how the death penalty was imposed. But these reforms failed to appeal to the common sense of ordinary citizens. A burglar who beat a homeowner to death would hang.

A rapist who murdered his victim would not face the death penalty. If someone poisoned you, they'd do time. But if they shot you, they'd be executed. Killing a prison guard triggered the death penalty, but murdering a child did not. Death sentences were passed on fewer and fewer occasions, and it became harder and harder to argue that hanging was in any. any way a deterrent to criminals.

In August 1964, a couple of petty criminals who'd stabbed a man during an attempted robbery were hanged on the same day. In other grislier cases, killers' lives had been spared, so many people were surprised that these two hangings had been allowed to go ahead. They would turn out to be the last. Goddard was by then in retirement, but even on his very last day in court he'd been sending business the hangman's way.

Albert Pierpoint had also retired before the abolition of his trade. He'd long combined stretching necks with pulling pints, but now committed himself full-time to running a pub. And Tending Bar gave him time to running a pub. to reflect on his previous occupation. If death were a deterrent, I might be expected to know, he wrote in his memoirs. I do not now believe that any one of the hundreds of executions I carried out has in any way acted as a deterrent against future murder. Capital punishment, in my view, achieved nothing except revenge.

For a full list of our sources, see the show notes at Tim Harford.com. Next week, I will be back early for an extra bonus episode. I am going to be joined by the one and only Malcolm Gladwell to discuss the death penalty and more. has just made a new series of revisionist history. It's called The Alabama Murders. It's going to be a great conversation, and I'll see you then. Cautionary Tales is written by me, Tim Harford, with Andrew Wright, Alice Fines, and Ryan Dilley.

It's produced by Georgia Mills and Marilyn Rust. The sound design and original music are the work of Pascal Wise. Additional sound design is by Carlos San Juan at Brain Audio. Ben Nadaf Haffrey edited the scripts. The show also wouldn't have been possible without the work of Jacob Weisberg, Greta Cohn, Sarah Nix, Eric Sandler, Christina Sullivan, Kira Posey and Owen Miller.

You can support Cautionary Tales by joining my Cautionary Club at patreon.com slash cautionary club for exclusive bonus episodes, newsletters, ad-free listening and other exciting perks. Alternatively, you can join Pushkin. Plus on our Apple show page for continued benefits from our show and others across the Pushkin Network. I'm Jonathan Goldstein, and on the new season of heavyweight.

And so I pointed the gun at him and said this isn't a joke. A man who robbed a bank. when he was 14 years old. And a centenarian rediscovers a love lost 80 years ago. How can a 101-year-old woman fall in love again?

Listen to heavyweight wherever you get your podcasts. This is an I-Heart podcast.