Harry Roberts v Reggie Kray, the Fight in the Prison Gym

Reggie Kray asked Harry Roberts, very quietly and very politely, whether he could train with him.

It was a prison gym, some time after the twins were sent down in 1969. Roberts had been inside for more than two years by then. He was the most hated prisoner in Britain, the man who had shot dead two police officers in a London street, and he was serious about his weights. Reggie was new to them. Roberts said yes. Reggie could train with him.

Roberts did his set. Then it was Reggie's turn, and he went to lift the same weight.

It's better if you start off on some lighter weights, get used to it

Harry Roberts, to Reggie Kray, as he told it in 2004

What happened next is Harry Roberts's own story. He told it in 2004, on a Sunday afternoon in his cell at Channings Wood prison in Devon, to a younger prisoner he trained with, while the two of them watched the Grand Prix with a cup of tea. That prisoner later told it on film. No officer's report of the fight has ever surfaced, and Reggie Kray never gave his side.

On the afternoon of 12 August 1966, three plain-clothes officers in an unmarked police car pulled up behind a van in Braybrook Street, Shepherd's Bush, next to Wormwood Scrubs prison. In the van were three armed robbers, Harry Roberts, John Duddy and John Witney.

Detective Sergeant Christopher Head was thirty. Temporary Detective Constable David Wombwell was twenty-five. PC Geoffrey Fox, who was driving, was forty-one. All three were shot dead. Roberts shot Wombwell and Head. Duddy shot Fox.

Roberts had served in the army in Malaya, and he put it to use. He went into the woods at Thorley, near Bishop's Stortford, and lived in a tent. There was a reward of £1,000 for him. He stayed free for ninety-six days, until police found him asleep in a hangar on a disused airfield at Blount's Farm, near Sawbridgeworth, on 15 November 1966.

In December that year he was convicted of all three murders and given life, with a recommendation that he serve at least thirty years. The judge told him he doubted any future Home Secretary would ever think fit to show him mercy.

Prison was always going to be strange for him. To the authorities and to every police officer in the country he was the worst of the worst. To some of the men on the landings he was something else. A chant about him started outside Shepherd's Bush police station after his arrest, and spread to the football terraces, where it was sung for years.

Roberts did not need anyone's approval. He was a robber, not a gang man, and by his own account he had little time for the Krays. He told his gym partner in 2004 that the twins had once demanded a cut of a robbery he had done, and he had turned them down. He would not go to meet them either. The twins, he said, had a habit of having men waiting in the back room when you walked in. He was not frightened of them. In those days, he said, he always carried a gun.

To Roberts, men like himself and his crew were the ones who earned the money. The Krays were the ones who wanted a share of it.

Then, in 1969, the twins came to prison too.

Roberts was well into his training by the time Reggie arrived. The way he told it, the two men barely knew each other, and Reggie knew exactly who Roberts was.

Reggie had been a professional boxer as a young man, and he was the twin people who knew them both called the more dangerous of the two. Ronnie was the one with the illness and the temper. Reggie was quieter, and colder.

When Reggie stepped up to lift the same weight Roberts had just done, Roberts stopped him. He meant it kindly, he said. "Look, Reg," he told him, "you're only just getting into weights. It's better if you start off on some lighter weights, get used to it. I'm sure we can work you up quick."

Reggie's face did not move. According to Roberts, he thanked him for his advice. He had been thinking the same thing himself, he said. Then he walked off.

Roberts stood there wondering whether he had upset him. He decided he had not, or that it did not matter, turned back to the bar and carried on with his session.

The next thing he knew there was a bang on the side of his head. He spun round. It was Reggie Kray.

The two men went at each other. Roberts said they traded punches, went down onto the floor of the gym, and carried on fighting there until they were broken up. Both of them, he said, still wanted to get at each other when they were pulled apart.

It had all been about the weights. Reggie, in Roberts's telling, had taken the advice as an insult. He had heard a man tell him he was not strong enough to lift what another man could lift, and that was not something a Kray let go.

What surprised Roberts most was how it ended. The next day, he said, Reggie came and found him and shook his hand, and that was the end of it. There was no war. There was no grudge carried round the landings. Two of the most dangerous men in the system had settled it on a gym floor and then put it away.

In his telling, nobody won.

Reggie Kray served more than thirty years. He was released on compassionate grounds with terminal cancer in August 2000 and died that October. Ronnie died in 1995, still a Broadmoor patient.

Roberts outlasted them both. He made several escape attempts, once with fake pistols made from cotton reels and wax. In 1999 the writer Kate Kray reported that he showed no remorse, and that he baked apple pies decorated with pastry scenes of policemen being shot. In 2001 he was moved to an open prison, then sent back to closed conditions within months over allegations of drug dealing and smuggling.

By 2004 he had worked his way down the system to Channings Wood, near Newton Abbot, a category C prison set in open fields. He lived on its enhanced block, a separate unit with its own small gym, where lifers were prepared for their next move. Men with a minor injury could get on what the prison called remedials, twenty minutes in the gym every morning, and Roberts was on the bench press nearly every day. He was an old man who did not look like one. With his shirt off, the man who spotted him on the bench press said, he had the body of a thirty-year-old. He was nearly seventy.

The Parole Board approved his release in October 2014, against fierce opposition from the families of the three officers and from the police. He walked out on 11 November 2014, aged seventy-eight, after forty-eight years. He died in hospital on 13 December 2025, aged eighty-nine.

He never claimed the fight with Reggie Kray as a win. The Krays had built their names on making men afraid of them. Harry Roberts's story is about a man who was not.

Stories like this one are in our book on Britain's most dangerous prisoners.