The Greatest Heist of the 20th Century Shows Why Heists Do Not Pay

Bruce Reynolds, leader of the gang, which committed the 2.6 million pound 'Great Train Robbery' in August 1963.
Bruce Reynolds, leader of the gang, which committed the 2.6 million pound ‘Great Train Robbery’ in August 1963, outside Linslade Court, Buckinghamshire, November 18th, 1968.

Photo by Paul Popper/Popperfoto/Getty Images

I don’t want to let too much time pass without acknowledging the recent death of Bruce Reynolds, the British criminal who masterminded one of the greatest heists of modern times: 1963’s Great Train Robbery. Reynolds led more than a dozen men in a plot to hijack a Royal Mail train that was carrying about 2.6 million pounds in small bills, the equivalent of about $60 million today. The heist succeeded, though its aftermath reveals why such grandiose criminal plots are few and far between.

The suave, charismatic Reynolds was a criminal straight out of the movies. He wore tailored suits, drove an Aston Martin, and mingled in smart society. As Piers Paul Read put it in The Train Robbers, Reynolds was “propelled by an intense romanticism” that led him to consider careers in journalism, science, and the military. Eventually, he settled on more lucrative pursuits, and he formed a group that “specialized in top-class crime.”

In 1963, Reynolds and his confederates learned that a cash-laden mail train regularly left Glasgow for London, and began devising a plan to rob it. Reynolds built a team: musclemen to intimidate the train personnel, an expert to tamper with the rail signals, an engineer to drive the train. On the night of Aug. 8, the team fooled the train into stopping, and then, after bludgeoning the engineer into submission, stole 121 bags filled with money and made their escape. Afterwards, they holed up in a farm to divide the loot and celebrate, playing Monopoly using the real money they had stolen. Fade to black, roll credits.

OK, this non-cinematic heist didn’t really have a happy ending. Days after the robbery, Scotland Yard discovered the robbers’ hideout. It was covered in fingerprints, which made it easy to identify and capture most of the participants before they’d had time to spend their shares. Many of the robbers received 30-year jail sentences—extraordinarily harsh for a largely non-violent robbery—which some of them served in maximum security conditions. The police recovered just a small fraction of the money that had been stolen. Nevertheless, upon their release, some of the robbers found that the fortune they thought was awaiting them had been sapped by unscrupulous friends and associates.

A few of the train robbers escaped prison or eluded capture, for a time. But their lives were not carefree. They moved constantly to avoid detection; much of their money was spent underwriting their flight. Their funds evaporated, and by 1968 all but one had been brought to justice. The exception was Ronnie Biggs, who escaped from prison in 1965 and fled overseas, first to Australia and then to Brazil, which lacked an extradition treaty with the United Kingdom. Biggs, who lived there openly for decades, became a public figure of sorts, entertaining visitors at his house and even recording a few tracks with the Sex Pistols. But he missed England, and in 2001 voluntarily surrendered and returned to prison. He remained there until 2009, when he was released on compassionate grounds.

As for Bruce Reynolds, after five years living lavishly on the lam in Canada and Mexico, the near-bankrupt criminal mastermind returned to England in 1968. He was captured later that year and sent to prison, where he served 10 years before being paroled in 1978. He later returned to prison for drug trafficking; after being released for that crime, he attempted to trade on his notoriety as the Great Train Robbery’s architect, writing an autobiography and appearing in the media. A BBC obituary noted that, by 1995, Reynolds was “living on income support in a south London flat supplied by a charitable trust.”

The aftermath of the Great Train Robbery shows why high-profile heisting is a bad career move for criminals. Big plans rarely go off without a hitch. Evidence is almost always left behind, and the more public the crime, the more motivated the police are to find that evidence and use it to make a collar.

If they were thinking pragmatically, the train robbers would have been better off sticking to simpler scores. Then again, Bruce Reynolds wouldn’t have been memorialized in the New York Times if he’d stuck to the small time. Was it worth it? The Great Train Robbery did bring some of its participants fame and other intangible rewards. The heist was even dramatized in the 1988 film Buster, in which Phil Collins played title character Buster Edwards, a member of Reynolds’ gang who, after the robbery, went on the lam before realizing that the love and respect of his family was more important than his freedom. The movie ended with Edwards leaving prison and opening a flower stand.They all lived happily ever after. Roll credits.

In truth, the real-life Buster Edwards did run a train station flower stall after leaving prison in 1975. But he found the work boring, and not particularly lucrative. He hanged himself in 1994. Yeah, not such a happy ending.