Mark Mason

The greatest – and strangest – prison breaks in history

Poor old Daniel Khalife. He must have thought his exit from HMP Wandsworth, hidden underneath a delivery van, would win ‘Most Creative Prison Escape of the Week’. But actually that title had already been nabbed by Danelo Cavalcante, who stood in a narrow external passageway at Pennsylvania’s Chester County prison, leaned forward so his hands were on the wall facing him, then placed his feet on the wall behind and ‘crab-walked’ upwards, his body parallel to the ground.

Khalife’s escape isn’t even the most inventive in Wandsworth’s history. His van was a normal one – the removals vehicle parked outside the prison by the team helping Ronnie Biggs in 1965 had a sliding panel cut into the roof and a platform lift inside, which the team extended to reach the top of the wall. For sheer Britishness, though, you need the spy George Blake’s escape from Wormwood Scrubs the following year. The rungs in his rope ladder were knitting needles. 

Hollywood loves a prison escape. Some are fictional, like The Shawshank Redemption, but some are based on real events. Escape from Alcatraz is accurate in having the inmates make papier-mâché heads to convince the guards they are still in bed (the hair came from the prison’s barber shop), and gluing together 50 stolen raincoats to form an inflatable raft. 

Anyone can bribe a screw to look the other way. The Mexican druglord Joaquín ‘El Chapo’ Guzmán did that with his mile-long tunnel in 2015 as well as his earlier escape in a laundry trolley. But a really impressive plan needs cunning. The South Korean robber Choi Gap-bok was a yoga expert, which meant that, after applying skin lotion to himself, he was able to squeeze through the 6x18in slot used to deliver food through his cell door.

Another ruse is the place-swap. The young Kray twins once took advantage of the ‘twins’ bit when Ronnie was inside and Reggie was free: the latter visited the former, put on his glasses and stayed there while Ronnie walked calmly away. In 1715, the day before his planned execution, the Earl of Nithsdale was visited at the Tower of London by his wife and several female friends, all of whom were wearing extra layers of clothes. The Earl put these on, together with some make-up, then slipped out while his wife remained in the cell, pretending to talk to him. In 2012 a Brazilian criminal and his wife tried the same trick: the man made it all the way to the bus stop outside the prison before a policeman noticed that he was struggling to walk in high heels.  

For maximum points, you need to make the authorities look stupid. Twelve inmates left an Alabama jail in 2017 by getting a guard to unlock a door for them – they’d obscured the sign warning that it led to the outside by smearing it with peanut butter. And Michael Vaujour’s 1986 escape from a Paris prison was aided by grenades with which he threatened officers. Except they weren’t grenades. They were objects he’d painted to look like grenades. Specifically, they were nectarines.