I don’t know if you’ve ever been locked in a concrete box, day after day, night after night. Every morning you wake up and think “F**k, I’m still here!”. No one appreciated freedom more than those who don’t have it. When I was locked up in Pentonville I remember looking out the high window (by perching my 6’3″ frame on a lateral gas pipe until my feet became too hot to bare) and seeing the simplicities of the outside world: a postie doing their rounds, a mother on the school run, even a homeless man wandering around brought great envy to my eyes.
Bear in mind, I was serving a maximum of 2 years, with a real possibility of going home after just 4 months. Albeit, we were under COVID lockdown conditions so my time was a bit more boring and isolated than the typical custodial sentence, but it had me thinking, what if I was serving 10 years? 20 years? A whole life order?! Surely in that case there would be one thing on my mind: escape.
At times I would observe the weak points in security around my cell and the wing as a whole, there were none. And any “hack” I could even attempt would leave me exposed to every officer in the prison ready to mob me as soon as I broke my leg from falling 5 storeys out of my cell window.
But for some that is a risk they’re willing to take, there are people who know they may never see their loved ones again, everything they hold dear in the world will be gone or alienated by the time they walk out those gates (and that’s a big IF). So is it any wonder that prisoners try to escape? Not your typical PWIT 2-do-1s1 but more like the double murder charged, found guilty by jury and failed appeal-types.
In today’s article we’re going to look a how desperate (and cunning) some UK prisoners can be while we look at their escapes from the nick, how far they got and how they were ultimately sent back.
10. Kyle Eglington — The Underpants Escape, 2022
Prison/custody: Prison transport van, Dorset
Time at large: About two days
Escape rating: 6/10
We’ll start with an escape that sounds less like The Shawshank Redemption and more like the beginning of a stag-do story.
In March 2022, 32-year-old Kyle Eglington was being transported in a prison van in Poole when he allegedly assaulted a security officer and legged it.
There was one minor problem with his newfound freedom:
He was reportedly wearing nothing but his underpants and socks.
A major search followed, involving armed police and a police helicopter. Officers even warned that he might have shaved his head and beard in an attempt to change his appearance.
Considering he had started his life as a fugitive dressed for bed, that’s quite the transformation.
His freedom didn’t last long. Police arrested him in the early hours of the following Monday.
There is something beautifully British about the whole thing. You’ve escaped custody, helicopters are looking for you, armed police are on the streets…
…and you’re running around Dorset in your pants.
Brazen? Absolutely. Successful? Not particularly.
9. Julien Chautard — Pentonville’s Human Undercarriage, 2009
Prison: HMP Pentonville
Time at large: Four days
Ending: Gave himself up
Fourteen years before Daniel Khalife became famous for disappearing beneath a vehicle, another prisoner reportedly pulled essentially the same trick at Pentonville.
French arsonist Julien Chautard had just arrived at the jail from Snaresbrook Crown Court in 2009.
Instead of settling into his new accommodation, Chautard escaped by clinging to the underside of the prison van that had delivered him.
And somehow…
the van drove back out with him underneath it.
He remained free for four days.
Then came perhaps the strangest part: rather than being hunted down and dragged back inside, Chautard returned voluntarily and surrendered himself to police.
Imagine successfully getting out of Pentonville and then, four days later, thinking:
“You know what? Fuck it. Take me back.”
Having spent time in Pentonville myself, voluntarily returning wouldn’t have been high on my list.
8. John Massey — The 64-Year-Old Lifer Who Climbed Out of Pentonville, 2012
Prison: HMP Pentonville
Sentence: Life imprisonment for murder
Age: 64
Time at large: Two days
If I had struggled to identify an escape route while sitting in Pentonville in my twenties, imagine how humbling it is knowing that a 64-year-old lifer actually managed it.
John Massey had been sentenced to life for a 1975 murder.
And this wasn’t even his first taste of disappearing from custody. After previous parole problems and a spell at open prison, Massey eventually found himself back inside Pentonville.
Then, on 27 June 2012, he escaped.
At 64 years old.
There is something almost offensive about that from a security perspective.
This wasn’t some 21-year-old athlete seeing an opportunity and sprinting for his life. This was a man who had already spent decades dealing with the prison system managing to get himself out of a Victorian Category B jail in the middle of London.
His second spell of freedom was brief. Police recaptured him in Kent two days later.
Still, if I ever return to Pentonville and hear an officer telling prisoners that escape is impossible, I now know the appropriate response:
“Tell that to the pensioner.”
7. John Anslow — His Mates Brought Sledgehammers, 2012
Custody: Prison van from HMP Hewell
Status: Category A
Time at large: Months
Escape rating: 8/10
Some prisoners carefully plan how they’re going to break out.
John Anslow apparently had another solution:
Get the boys to come and get you.
In January 2012, Anslow was being transported from HMP Hewell to Stafford Crown Court while facing a murder charge.
A car intercepted the prison van.
Three masked men got out.
Two were carrying sledgehammers.
They smashed the windows of the vehicle, assaulted the driver and sprung Anslow from custody before making their getaway.
This wasn’t some low-risk prisoner being taken to magistrates’ court, either.
Anslow had been designated Category A — the category reserved for prisoners whose escape would pose a serious danger to the public, police or national security.
His escape was significant enough that the Justice Secretary ordered an inquiry. Contemporary reporting described him as the first Category A prisoner to escape custody in more than 17 years.
Whatever you think of the people involved, there’s no denying the audacity.
Most escape plans involve finding a weakness in the prison.
This one involved bringing your own demolition crew.
6. Matthew Baker & James Whitlock — The Pentonville Dummy Trick, 2016
Prison: HMP Pentonville
Time at large: Roughly three and six days respectively
Best detail: The fake bodies
Now we’re back at my old residence.
In November 2016, Matthew Baker and James Whitlock managed something every Pentonville prisoner has probably fantasised about at least once:
They got over the wall.
Baker had recently been convicted of attempted murder. Whitlock was on remand over allegations involving ATM burglaries.
But it’s the theatrical element that earns them their place here.
Before disappearing, the pair stuffed their beds to make it look as though they were still sleeping in them.
Proper Escape from Alcatraz shit.
They got through their cell security, made their way across the prison structure and escaped over the perimeter. Astonishingly, staff reportedly didn’t realise the men had vanished until around 15 hours after they were last seen in their cell.
Baker lasted about three days before being arrested in east London, less than 10 miles from the prison.
Whitlock lasted longer, but he too was eventually caught.
This one particularly fascinates me because I’ve actually lived behind those walls.
I’ve looked at them.
I’ve looked at the windows.
I’ve looked at the officers.
I’ve looked at the drop.
And my conclusion was always:
“Nah.”
These two apparently reached a different conclusion.
5. Daniel Khalife — The Great Wandsworth Vanishing Act, 2023
Prison: HMP Wandsworth
Status: On remand
Time at large: Around 75 hours
Escape rating: 8/10
Daniel Khalife’s escape caused national pandemonium precisely because prison escapes like this have become so rare.
Khalife was a former British Army soldier being held at HMP Wandsworth while facing terrorism and espionage-related charges.
On 6 September 2023, the 21-year-old disappeared from the prison.
The escape involved the food-delivery operation where he worked in the kitchen. Khalife concealed himself beneath a catering vehicle as it left Wandsworth. He later pleaded guilty to escaping lawful custody.
Then Britain collectively lost its mind.
Ports and airports faced heightened checks. Police searched Richmond Park. Helicopters, dogs and officers were deployed across London.
For roughly 75 hours, Khalife remained free.
Eventually a plain-clothes counter-terrorism officer spotted him near a canal in west London and pulled him from a bicycle.
Later investigations also established that Khalife had received assistance while on the run, including £400 arranged through an associate, helping him obtain a phone and other items.
All that national attention…
…because one prisoner managed to leave Wandsworth without using the front door in the conventional manner.
4. The Parkhurst Three — The Escape From an Island Prison, 1995
Prison: HMP Parkhurst, Isle of Wight
Prisoners: Matthew Williams, Keith Rose and Andrew Rodger
Time at large: Around four/five days
Minor problem: They were still on an island
Parkhurst was supposed to be serious business.
Among the three men who escaped in January 1995 were two Category A prisoners.
The men managed to get out of the prison and over its perimeter.
Then they encountered the slight logistical flaw in their otherwise impressive plan:
Parkhurst is on the Isle of Wight.
Escaping the prison was only stage one.
Escaping the fucking island was stage two.
Official parliamentary accounts established that the men had exploited serious security failures before getting through the perimeter. Their disappearance prompted an enormous search and eventually a major review of prison security.
For days, police searched the island.
Rose and Rodger were eventually caught in open countryside roughly six miles from the prison. Williams briefly managed to evade capture again before being caught about 90 minutes later.
All three ended up back inside.
The escape was sufficiently embarrassing that it contributed to a much wider reassessment of security in British prisons.
But it wasn’t even the most embarrassing high-security escape of the 1990s.
That honour goes to…
3. The Whitemoor Six — The “Escape-Proof” Prison That Wasn’t, 1994
Prison: HMP Whitemoor
Prisoners: Six
Security: Special Secure Unit
Result: All six recaptured
Whitemoor wasn’t supposed to be Pentonville.
This was a high-security prison containing some of the most dangerous prisoners in the country.
And within it was a Special Secure Unit.
In other words:
“You’re already in a prison, but you’re so dangerous we’ve put another prison inside the prison.”
On 9 September 1994, six prisoners escaped from that unit.
And they weren’t harmless opportunists.
They had firearms.
During the breakout, a prison officer was shot and wounded. The men made it beyond the prison perimeter, triggering a huge response.
Four were caught almost immediately.
The remaining two managed about half a mile before police arrested them.
So, as escapes go, their freedom was absolutely shite.
But that’s not why this one ranks so highly.
It’s because they had managed to get out of a Special Secure Unit in a high-security prison while armed.
The subsequent Woodcock inquiry examined exactly how something so catastrophic had been possible, and security at Whitemoor and other high-security prisons was tightened afterwards.
The prison system had just suffered a massive embarrassment.
Four months later…
Parkhurst happened.
Not a great year for the Prison Service.
2. Kendall & Draper — The Gartree Helicopter Escape, 1987
Prison: HMP Gartree
Prisoners: John Kendall and Sydney Draper
Method: A FUCKING HELICOPTER
Escape rating: 10/10
Forget bedsheets.
Forget vans.
Forget tunnelling.
In December 1987, two Category A prisoners escaped HMP Gartree in the manner normally reserved for a terrible 1980s action film.
A helicopter landed inside the prison.
The aircraft’s pilot had been hijacked by an armed passenger and forced to fly to Gartree.
The helicopter descended into an open exercise area.
High-risk prisoners John Kendall and Sydney Draper got aboard.
And then it simply flew away.
That isn’t an urban legend. The Home Secretary subsequently confirmed the basic facts to Parliament.
Imagine being another prisoner watching this unfold.
You’re spending months quietly considering whether you could somehow defeat a window grille with a sharpened toothbrush…
…and two blokes have apparently ordered an Uber Helicopter.
The aircraft landed a short distance away, where the escapees continued their getaway by road.
Both men were eventually caught, as was Andrew Russell, who had helped facilitate the escape.
But the incident exposed such an obvious vulnerability that it contributed to changes in how Britain’s most dangerous prisoners were managed. A later government inquiry specifically referenced the 1987 helicopter-assisted escape of two high-security prisoners from Gartree when discussing the evolution of enhanced security arrangements.
There’s brazen.
There’s audacious.
And then there’s landing an aircraft in a Category A prison and flying two prisoners out.
Yet somehow…
That still isn’t number one.
1. The Maze Prison Escape — 38 Prisoners Walk Out, 1983
Prison: HM Prison Maze, Northern Ireland
Prisoners who escaped: 38
Initially still at large: 28 after the immediate recaptures
Scale: Unmatched
If we’re including the entire United Kingdom, nothing else on this list really comes close.
On 25 September 1983, 38 republican prisoners escaped from the Maze.
This wasn’t somebody spotting an unlocked door.
It became a violent, coordinated takeover.
Prisoners produced weapons inside H Block 7, overpowered officers and took control of the block. A prison officer was shot in the head but survived. The prisoners took officers’ uniforms and seized a prison meal-delivery van.
Thirty-eight prisoners were driven toward the main gate.
The vehicle passed through two manned gates without being searched.
At the main gate, the escape descended into violence. Prison officers were seriously injured and officer James Ferris was killed.
The prisoners then fled on foot.
Ten were caught almost immediately.
Nine more were recaptured over the following days.
But 19 remained at large when the government reported back to Parliament the following month.
The scale is difficult to comprehend in the context of the modern British prison system.
Daniel Khalife escaping alone in 2023 triggered a national manhunt and days of wall-to-wall news coverage.
The Maze lost 38 prisoners in one incident.
The subsequent Hennessy inquiry examined the security failures surrounding the escape and produced recommendations for improving the prison’s security.
Whatever political mythology subsequently grew around the event, it’s important not to romanticise what actually happened: this wasn’t a cheeky prisoner climbing through a toilet window. Prison officers were attacked, several people were seriously injured and one officer lost his life.
But judged purely on scale and audacity?
There has been nothing else like it in modern British prison history.
Honourable Mention: The Brixton Two
There is one escape I struggled to leave out.
In July 1991, Pearse McAuley and Nessan Quinlivan, two Category A high-risk prisoners facing extremely serious charges, escaped from HMP Brixton.
A firearm had made its way into the prison.
After attending Catholic Mass, the pair overpowered their escorts, got over the perimeter and escaped into London. During the getaway, a motorist was shot in the leg and his vehicle was taken.
Then — brilliantly illustrating how quickly an extraordinary escape can become mundane — they took a taxi to Baker Street station.
From Category A prison…
to armed breakout…
to:
“Baker Street please, mate.”
They deserve an honourable mention because unlike most of our escapees, the story didn’t end with police catching both men a couple of days later. Their cases became tangled with Ireland, extradition and the politics of the Troubles.
So, Is Escaping From a British Prison Actually Possible?
Technically?
Yes.
Realistically?
Good fucking luck.
Looking through these cases, there’s an obvious pattern.
The spectacular escapes generally weren’t the result of some genius prisoner spending twenty years secretly scraping through reinforced concrete with a spoon.
They exploited moments when the normal security system broke down — transport, outside assistance, catastrophic procedural failures or vulnerabilities that subsequently got fixed.
And that’s probably why sitting in my cell at Pentonville looking for an escape route seemed so hopeless.
I was looking at the finished product.
Modern prison security has been shaped partly by every lunatic on this list who came before me.
Someone escapes from a supposedly secure unit? Procedures change.
Someone goes over a wall? The perimeter changes.
Someone gets sprung from a van? Transport procedures get reviewed.
Someone escapes in a helicopter?
Presumably somebody at the Ministry of Justice has to sit down and write a policy entitled:
“Please Don’t Let Helicopters Land in the Fucking Prison.”
The irony is that successful escapes help make the next escape more difficult.
And even when prisoners do make it beyond the wall, that’s when an entirely different problem begins.
Getting out is one thing.
Staying out — without money, identification, somewhere safe to sleep, or half the country’s police looking for you — is something else entirely.
That’s why so many prison escapes end the same way.
A few hours of freedom.
A few days if you’re lucky.
Blue lights.
Handcuffs.
A prison van.
And then that horrible familiar sound:
the gate closing behind you again.
- PWIT: Possession with intent to supply, 2-do-1: prison slang for a sentence of 2 years that typically results in early release after 9-12 months. ↩︎
[2] The Guardian, Dorset police arrest man reported to have escaped prison van in underpants, 29 March 2022. Source
[3] Wikipedia, HM Prison Pentonville — section covering Julien Chautard’s 2009 escape. Source
[4] ITV News, Convicted murderer escapes from Pentonville Prison, 27 June 2012. Source
[5] Wikipedia, HM Prison Pentonville — history of escapes from the prison. Source
[6] The Guardian, coverage of John Anslow’s escape from a prison van while being transported from HMP Hewell to Stafford Crown Court, January 2012. Source
[7] The Guardian, One HMP Pentonville fugitive Matthew Baker convicted of attempted murder, 7 November 2016. Source
[8] The Guardian, Pentonville inmate feared for his life before escape, court told, 15 June 2017. Source
[9] The Guardian, Pentonville prison escape: Matthew Baker caught in east London, 10 November 2016. Source
[10] ITV News, Daniel Khalife pleads guilty to escaping prison, 11 November 2024. Source
[11] Evening Standard, reporting on Daniel Khalife’s recapture following approximately 75 hours at large, September 2023. Source
[12] Metropolitan Police, Man convicted of assisting Daniel Khalife after he escaped from prison. Source
[13] UK Parliament, House of Commons Hansard, Prison Service, 10 January 1995 — statement concerning the escape of three prisoners from HMP Parkhurst. Source
[14] The Independent, Police and mud combine to capture Parkhurst escapers, January 1995. Source
[15] UK Parliament, House of Commons Hansard, 19 December 1994 — discussion of the escape of six prisoners from the Special Secure Unit at HMP Whitemoor. Source
[16] UK Government, Report of the enquiry into the escape of six prisoners from the Special Security Unit at Whitemoor Prison, Cambridgeshire (Woodcock Report). Source
[17] UK Parliament, House of Commons Hansard, Gartree Prison (Escape), 21 January 1988 — official statement concerning the helicopter-assisted escape. Source
[18] The Independent, Faces of the terrorists and the criminal who didn’t get away, September 1994 — retrospective reference to the Gartree helicopter escape. Source
[19] UK Government, Review of the Security of High Risk Prisoners — historical discussion of the 1987 helicopter-assisted Gartree escape and subsequent high-security arrangements. Government report (PDF)
[20] UK Parliament, House of Lords Hansard, Maze Prison: Escapes, 24 October 1983 — official account of the mass escape. Source
[21] UK Parliament, House of Commons Hansard, Maze Prison, 24 October 1983 — government statement concerning the escape and subsequent recaptures. Source
[22] CAIN Web Service, Ulster University, Report of an Inquiry into the Security Arrangements at HM Prison, Maze (Hennessy Report), 1984. Source
[23] UK Parliament, House of Commons Hansard, Brixton Prison: Escapes, 8 July 1991 — official statement on the escape of Pearse McAuley and Nessan Quinlivan. Source
[24] Wikipedia, Nessan Quinlivan — biographical background and subsequent extradition proceedings. Source
[25] UK Government History Blog, What’s the Context? 22 October 1966: Spy George Blake escapes from Wormwood Scrubs, 21 October 2016. Source













