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Bruce Reynolds said he wanted to "make his mark" when masterminding the Great Train Robbery - but said the infamous heist became his curse in later life.
Using inside information on the movement of valuables, the antiques dealer assembled a gang to raid a night train in Buckinghamshire in August 1963, with the group making off with £2.5 million in used bank notes.
The eventual death of train driver Jack Mills further blackened the heist.
While co-conspirator Ronnie Biggs spent nearly four decades on the run after escaping from prison in 1964, Reynolds evaded capture for five years, spending time in Mexico and Canada, before returning to England.
He was captured in Torquay in 1968 and jailed for 25 years but was released in 1978, alone and penniless.
Reynolds spent another three years in prison in the 1980s for dealing amphetamines.
He later said his part in the 1963 crime meant no-one wanted to employ him, legally or illegally.
Bruce Reynolds, the mastermind of the Great Train Robbery, has died - just before the 50th anniversary of the infamous heist, often hailed as one of the most audacious crimes of the 20th Century.
His son Nick Reynolds confirmed his 81-year-old father passed away in his sleep after recently falling ill.
"He hadn't been well for a few days and I was looking after him," he said. "I really can't talk at the moment. I can confirm that he has passed away and he died in his sleep."
Bruce Reynolds led the gang that made off with more than £2.5 million (worth £40 million today) when they held up the Royal Mail travelling post office which ran between Glasgow and London in August 1963.
Bruce Reynolds, the man behind the 1963 Great Train Robbery, has died aged 81, reports say.
Reynolds, who lived out his last years in Croydon, south London, had been in poor health in the last few months and died just before the 50th anniversary of the famous crime.
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There have been bigger heists since 1963. But in my primary school playground, the only game to play was Cops and Great Train Robbers.