For most people, the phrase “life imprisonment” carries a simple promise: you never walk free again.
Yet Harry Roberts, a man convicted of murdering three unarmed police officers, spent more than a decade outside prison walls after serving 48 years.
His death last Saturday at 89 has reopened old wounds and revived a question that never quite went away — how did this happen?
The Day That Shook Shepherd’s Bush
The killings took place on a summer afternoon in August 1966, near Wormwood Scrubs prison in west London.
Roberts and his accomplices, John Duddy and John Witney, were sitting in a van, preparing for an armed robbery.
Three officers approached them: Detective Sergeant Christopher Head, 30; Detective Constable David Wombwell, 25; and Constable Geoffrey Fox, 41. None of the officers were armed.
What followed unfolded with terrifying speed.
Roberts opened fire with a Luger pistol, killing DS Head and DC Wombwell himself.
DC Fox was shot dead by Duddy. Two men were killed within around 30 seconds.
A third fell moments later. The judge would later describe it as the most heinous crime of its generation.
A Judge Who Expected Mercy Would Never Come
When Roberts was sentenced at the Old Bailey on November 15, 1966, he received three life sentences with a minimum tariff of 30 years.
Mr Justice Hildreth Glyn-Jones made his view clear, telling him he could not imagine any Home Secretary ever showing mercy given the scale of the crime.
The judge’s daughter, Anne Glyn-Jones, later said her father regarded Roberts as evil — and would have imposed the death penalty had it still been available.
Capital punishment, however, had been abolished just a year earlier.
Ninety-Six Days on the Run
While Duddy and Witney were quickly caught, Roberts vanished. For 96 days, he evaded capture, using his army training to survive outdoors. Scotland Yard launched its largest manhunt to date.
He was eventually found near Bishop’s Stortford in Hertfordshire, living in a makeshift den camouflaged with branches and plastic bags — a grim end to one of the country’s most intense searches.
A Prisoner for Nearly Half a Century
Roberts became one of Britain’s longest-serving inmates, spending almost five decades behind bars.
His accomplices never lived to old age: Duddy died in prison, while Witney was murdered after his release.
Despite the passage of time, Roberts never publicly showed genuine remorse.
Instead, his own words would later horrify those who remembered the fallen officers.
The Interview That Rekindled Outrage
In 2014 — the same year he was released — Roberts spoke to the Daily Mail and chillingly described the atmosphere during the killings as “electric.”
He recalled the moment he raised the gun, the sound of his heartbeat, and the officer collapsing after being shot point blank below the eye.
For many, it was confirmation of what they had long believed: that remorse had never taken root.
A Failed Parole Bid and a Trail of Threats
Roberts had already been denied parole in 2009 after threatening Joan Cartwright, her husband Peter, and their son James, who had given him work at an animal sanctuary during day release.
After Joan complained about his behaviour, Roberts threatened to kill the couple and repeatedly phoned her from prison.
Animals at the sanctuary were later attacked, deepening fears about his capacity for violence.
Release, and a Nation’s Anger
Despite this history, the Parole Board ruled in 2014 that Roberts could be released on licence.
The decision was backed by then deputy prime minister Nick Clegg — and condemned by many others.
Politicians across parties said anyone who kills a police officer should remain behind bars for life.
Sir Bernard Hogan-Howe, then Metropolitan Police Commissioner, was blunt: in this case, “life should have meant what it said.”
Freedom in Old Age
Roberts left HMP Littlehey in November 2014 at the age of 78.
He lived in sheltered accommodation in Peterborough under probation supervision, far from the streets where his name once inspired fear.
An associate later said he had gone into hospital and died suddenly from natural causes after a short illness — more than a decade after his release.
A Legacy That Refuses to Fade
Roberts’ death closes the final chapter of a story that has haunted British policing for nearly 60 years.
Yet the anger remains. For the families of Christopher Head, David Wombwell and Geoffrey Fox, and for many officers who followed them into service, the sense of injustice never eased.
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