Daniel Khalife’s escape follows a rich – and troubled – history of prison breaks

Prison breaks summon up conflicting feelings. At first, there is deep concern, a justifiable worry that an often-violent criminal is now on the loose. But then – as details of the escape emerge ­– there is a reluctant admiration for the man on the run and a thrill engendered not only by his resourcefulness but also of course by the chase. Hollywood knows this conflict all too well, which is why prison break movies invariably feature the wrongly imprisoned, in order to make our enjoyment of the escape more morally comfortable.

Unfortunately, there is no such comfort to be found in the escape of Daniel Abed Khalife from HMP Wandsworth on Wednesday and his capture. Khalife, who was being held on remand for terror offences, is far from the movie archetype of the falsely accused hero who deserves our sympathy and support. Instead his arrest on Saturday – having been yanked from a bicycle – should be cheered.

This is the problem with nearly all great prison breaks, although there are a few exceptions. Among them is that of the Jesuit priest, John Gerard, who had been imprisoned in the Tower of London in 1594 for running an underground Catholic ministry. After enduring years of torture, Gerard managed to escape in October 1597 by clambering along a rope that some accomplices had secured over the moat. Owing to his tortures, the 33-year-old Gerard found such gymnastics immensely difficult.

“I had gone three or four yards face downwards when suddenly my body swung round with its own weight and I nearly fell,” Gerard later wrote. “I was still very weak, and with the slack rope and my body hanging underneath I could make practically no progress.”

Despite the strain, Gerard made it to the other side, where a friend helped him clamber over the wall, before eventually getting him into a boat and rowing away. Gerard would live in freedom until he died 40 years later in Rome.

Gerard’s great escape not only reveals that busting your way out of places like the Tower of London and HMP Wandsworth certainly requires help on the outside, but also the fact that methods of escape have changed little over the centuries.

Take the escape of the train robber, Ronnie Biggs, who escaped from Wandsworth prison in 1965. While Biggs did not use a rope, he did use a rope ladder to scale a prison wall, which had been slung over by accomplices. While his fellow prisoners staged a scuffle to distract the wardens, Biggs hotfooted it over the wall. On the other side was not a boat, but a removals lorry, through the roof of which Biggs climbed and away to freedom. Even though his gang were a bunch of violent larcenous thugs, Biggs enjoyed a certain folk hero status while living in exile in Brazil, from where he eventually returned to be imprisoned once more in 2001.

The mid-1960s were not a great time for the prison service, because the year after Biggs escaped, an even bigger fish managed to wriggle free. This was George Blake, a former MI6 officer who had betrayed some of the West’s biggest secrets to the Soviet Union. In 1961, he had been sent down for 42 years ­– reputedly one year for each of the deaths that Blake had caused by his treachery – and in 1966 he found himself incarcerated in Wormwood Scrubs knowing that he was likely to be there until the end of the century.

Just like Gerard and Biggs before him, rope and accomplices were the keys to Blake’s escape, which was mounted on the evening of 22 October 1966. Along with two other inmates and while the guards were distracted watching a film, Blake climbed over a wall using a rope ladder which used knitting needles as rungs. He was held in safe houses for two months before eventually being smuggled by car across the Iron Curtain.

It was the 1970s and 1980s that would see escapes from British prisons becoming far more audacious and larger in scale, and this was chiefly because of the activities of the Provisional IRA – and in one instance, a seal.

In 1972, some IRA men who were incarcerated on a prison ship called HMS Maidstone in Belfast noticed that a seal was somehow able to swim through the cordon of barbed wire that surrounded the vessel. Not unreasonably, they felt that there had to be a gap, and one night in January, seven men, covered in butter and camouflage cream, slipped down the anchor chain and into the water. There then followed an icy 800-foot swim to the shore, during which they proved to be less aquatically nimble than the seal and repeatedly cut themselves on the barbed wire. Nevertheless, they made it and successfully crossed the border into the safety of the Irish Republic.

Such an escape by IRA men would seem like small beer compared to what the terrorist organisation achieved at the notorious Maze prison outside Belfast in 1983. A maximum security jail, the Maze was supposedly escape-proof, but that did not stop nearly 40 inmates from mounting an ambitious breakout.

On the afternoon of 25 September, some of the prisoners threatened their guards with knives and guns that had been smuggled to them, and then hijacked a lorry, onto which 38 IRA men boarded and drove off. During the violence that took place that day, six guards were either stabbed or shot, with one dying of his wounds. Just half the prisoners would be recaptured and the escape remains the largest prison break in British history.

Since then, escapes from British prisons have been on a much smaller scale, but the methods have remained ingenious. Take the case of two violent burglars, James Whitlock and Matthew Baker, who in November 2016 placed dummy heads in their beds at Pentonville prison in north London, before sawing through the bars of their cell. The two men then managed to get out of a window by removing an iron bar and by using tied-up bed sheets as rope, scaled the prison’s walls. Unfortunately for Baker, he broke his leg after dropping to the ground, and would be arrested two days later, with Whitlock arrested just a few days after that.

Doubtless, all prisoners who are recaptured will be disappointed – not least because their sentences will be invariably extended – and many will know that their chances of success will be small. But, just like prisoners of war, there is another motive for escaping rather than just wanting to get out – planning escapes alleviates boredom. And any escape, even though unsuccessful, proves to yourself that you have done something, anything, rather than just meekly sit out your sentence.

But despite all the ingenuity, we must be careful not to celebrate the likes of Khalife, Biggs and Blake. They are desperate individuals. The only benefit gained from their attempts is to teach those who guard them to make it harder for others to follow in their footsteps, or indeed rope ladders.

Guy Walters is an author, historian and journalist