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The mastermind of Britain's 1963 Great Train Robbery, Bruce Reynolds, died on Thursday aged 81 after a life that he said had been cursed by his role in one of the 20th century's most notorious crimes.
Reynolds was the brains of a gang that held up a mail train in southern England and made off with almost £2.6 million -- worth around £40 million today (47 million euros, $63 million).
His son Nick confirmed that he had died in his sleep.
"He hadn't been well for a few days and I was looking after him. I really can't talk at the moment. I can confirm that he has passed away and he died in his sleep," he said.
Born in London, the bespectacled Bruce Reynolds was an antiques dealer and petty criminal before his involvement in what at the time was Britain's biggest ever robbery.
Nicknamed Napoleon, he was responsible for planning the raid by 15 men on the Glasgow-London post office train as it passed through the southern English county of Buckinghamshire on August 7, 1963.
Train driver Jack Mills was struck on the head with a cosh during the robbery and was unable to work again. He died in 1970.
After the robbery Reynolds went on the run with a false passport to Mexico where he was joined by his wife Angela and his son.
They later moved to Canada but their £150,000 share of the cash from the robbery ran out and he came back to England, where he was captured in 1968.
Reynolds eventually spent 11 years in jail.
After his release in 1979, he worked as a consultant on the film "Buster", which starred rock star Phil Collins as fellow Great Train Robber Buster Edwards.
But in the 1980s he was jailed for three years for dealing amphetamines and by the end of his life he was reduced to living on state benefits in a tiny London flat.
He published his memoirs, "The Autobiography of a Thief", in 1995.
In the book he said the Great Train Robbery was a "curse" which meant that no one wanted to give him a job after his release.
"I became an old crook living on handouts from other old crooks," he wrote.
Another member of the gang, Ronnie Biggs, famously escaped from prison after less than two years and fled to Brazil.
Reynolds and his son Nick travelled to Brazil in 2001 to persuade Biggs to return to Britain after 35 years on the run to serve the rest of his prison sentence. Biggs was freed on health grounds in 2009.
Nick Reynolds went on to be a member of the British band Alabama 3, who wrote the theme tune to the US TV mafia series "The Sopranos".
In 2003 Bruce Reynolds was reunited with John Woolley, the policeman who found the gang's hideout at a farm near the scene of the robbery. The pair shook hands during the meeting at a village fete and reminisced about old times.
Family friend John Schoonraad said Reynolds had been suffering from a chest condition before he died.
He said that despite his past Reynolds was a "perfect gentleman" who no longer believed in crime.
"He said to me, 'Crime doesn't pay.' He's done his time, and he turned into a very nice man. I've always known him to be a real gentleman," he said.