Police mug shots of Ronnie Biggs on display at The National Archives in September 2005 in London, England. Biggs was on the run for 35 years. (Getty Images)
Justice Secretary Jack Straw said he had rejected the Parole Board's recomendation to allow Biggs, 79, to be released.
"Mr. Biggs is wholly unrepentant and the Parole Board found his propensity to breach trust a very significant factor," Straw said in a statement.
Along with 11 other gang members, Biggs robbed a Glasgow-to-London mail train in 1963 and stole 2.6 million pounds–about 30 million pounds ($49 million) in today's money. The crime became known as "The Great Train Robbery."
He was caught and sentenced the following year but escaped from prison after just 15 months.
He used his share of the loot to pay for plastic surgery and papers for a passage to Australia where he returned to his old job of carpenter and decorator. He later fled to Brazil via Panama and Venezuela.
His playboy lifestyle and cocky defiance of the British authorities made him a criminal legend, spawning several films and making heroes out of the villains in the eyes of millions around the world.
He surrendered to police in 2001 after 36 years on the run and is now serving the rest of his sentence at Norwich prison in eastern England.
Biggs has served 10 years of a 30-year sentence for one of Britain's most infamous crimes.
His son Michael, 34, said he and his family were devasted by Straw's decision.
"Even though he was on an embankment during the robbery, he has always expressed how sorry he was about it all and extended his sympathy to the train driver and the families concerned," he said.
He added his father was suffering from a fractured hip, spine and pelvis, is recovering from pneumonia and unable to walk, talk, drink or eat properly.
