What on Earth Was the Great Train Robbery?

Who robs a train past, like, 1873? That’s actually a question we’re still trying to answer.
What on Earth Was the Great Train Robbery?

Depending on the level of dork you are, you might have heard about the Great Train Robbery in a James Bond movie or a sci-fi video game, but just what the hell was the Great Train Robbery? Who robs a train past, like, 1873? That’s actually a question we’re still trying to answer. Allow us to explain.

The Great Train Robbery

Royal Mail train

(Hugh Llewelyn/Wikimedia Commons)

It all started when an associate of South West Gang members Gordon Goody and Buster Edwards introduced them to a mysterious Royal Mail employee known only as The Ulsterman who had a deal for them. It turns out mail trains carried a lot of money, so if they agreed to give him a cut of the take in exchange for the info to carry it out, it would make a good robbery.

The Planning

Bruce Reynolds, Ronnie Biggs, and their sons

(Unknown author/Wikimedia Commons)

Goody and Edwards brought the proposal to their boss, Bruce Reynolds, and things got Ocean’s Eleven in a hurry. Reynolds assembled a team of 15 gang members, associates, and inside men, including a railway specialist who knew how to rig train signals. They planned the heist for just after a bank holiday to maximize their loot of birthday cards from grandmas and whatnot.

Stopping the Train

In the middle of the night on August 8, 1963, train drivers Jack Mills and David Whitby were doing their train-driving thing when they stopped at a red light at Sears Crossing. It didn’t take long for them to realize there was something fishy about being stopped for that long in the middle of the night, so Whitby hopped out to investigate and was baffled to find an old leather glove covering part of the signal and a bunch of six-volt batteries wired up to another. Before he had time to figure out what he was looking at, his arm was grabbed from behind and a voice told him, “If you shout, I will kill you.”

Disabling the Driver

Train driver

(Richard Tao/Unsplash)

Whitby was escorted back to the train, where he found other masked men struggling with Mills, who was eventually knocked unconscious with a crowbar. In the meantime, other heisters disconnected the conductor’s car and the “high-value package” car directly behind it from the remaining 10 cars, where 75 postal workers were just sitting around, unaware that anything was wrong beyond a really annoying red light.

A Slight Hitch

Train deck

(Mathias Reding/Unsplash)

Sears Crossing was actually a pretty inconvenient place to do a robbery, so they intended to drive the train a little farther down the track after checking “bash the driver” and “break the train” off their list, but it turned out the man Reynolds’s buddy Ronnie Biggs had recruited to drive the train didn’t actually know how to drive this particular train. With a lot of exasperated sighing and much less eye contact, presumably, they had to wake up the driver they’d knocked out to drive them to their destination.

A Big Slip

The gang managed to get away with about $7 million ($40 million today), making the Great Train Robbery the largest cash theft in history, but as they left, one member instructed the postal staff to wait 30 minutes before calling for help. That gave the police an enormous advantage because it told them the gang’s hideout must have been less than a 30-minute drive from the site of the robbery, saving them a lot of time and gas driving all over the Queen’s kingdom.

The Only Way to Play Monopoly


(Joshua Hoehne/Unsplash)

That was true -- the gang fled to a nearby farmhouse that had been rented by the associate who introduced Goody and Edwards to the Ulsterman, where they celebrated their success in the dorkiest way possible for a group of freshly minted millionaire thugs: playing Monopoly. They did it with the money they stole, so that’s kind of funny, but they also left their fingerprints all over the game board, which made it really easy for police to identify them as a bunch of nerds.

Getting Paranoid

Royal Air Force helicopter

(Cpl Tim Laurence RAF/Wikimedia Commons)

They intended to lay low for several weeks, but after a few days, knowing the fuzz was hot on their tails and other things ‘60s gangsters said, the gang noticed Royal Air Force helicopters circling overhead and ditched their hideout. It turned out the helicopters weren’t even for them, but it was probably their only saving grace, as the police closed in five days after the robbery.


It took up to five years in some cases (like Bruce Reynolds, who fled straight from the hideout to Mexico), but eventually, all but two identified robbers were caught and convicted, sentenced to a total of 307 years in prison. In their retributive fervor, however, the courts also convicted two men who were later exonerated, one who helped to rent the hideout in exchange for a cut of the take but had no idea of the scale of the robbery and another who just gave one of the gang members a couch to crash on. The latter ended up dying in prison, so that’s less than ideal.

Prison Breaks


(Christian Lue/Unsplash)

The Great Train Robbers had sort of become folk heroes, so not long after he was imprisoned, one of the gang members, Charles Wilson, was freed by a fan club of London criminals. He fled to Mexico to hang out with Reynolds but decided he preferred snow and relocated to Montreal, where he and his family became such pillars of the community that it lobbied to let his family stay after he was recaptured four years later. Ronnie Biggs made his own impressive escape by leaping over a wall and into a furniture truck and actually managed to live undetected in Australia and Brazil until 2001, when he returned to the U.K. for medical treatment. There’s really no beating that N.H.S.

The Ulsterman

Man in silhouette

(Joe Shields/Unsplash)

In 2014, Goody -- the last living person who had met The Ulsterman -- identified him as Irish postal worker Patrick McKenna, but that was weird because McKenna was known as a “quiet churchgoing man” who never seemed to have much money. It’s possible it was stolen from him or, as his family believes, he may have donated it all to the Catholic Church, but it’s also possible that Goody was a lying con man. Others have theorized that The Ulsterman was a gang associate named Sammy Olsterman and everyone just misheard his name.

Other Unidentified Heisters

Three other men involved in the heist have remained unidentified to this day. Two of them were associates of associates of the gang known by the aliases Bill Jennings and Alf Thomas who were little more than hired hands, but more interesting is the substitute train driver whose name Ronnie Biggs never bothered to learn and who probably never even got his share of the money. A historian managed to track him down in the ‘70s, but considering the circumstances and the man’s poor health at the time, he decided not to out him.

Deglorifying the Robbery

Train Robbers Bridge

(Spborthwick/Wikimedia Commons)

The Great Train Robbers became such sensational public figures that the train car they robbed was ceremoniously burned at a gathering of police and postal workers to prevent fans from seeking it out. It must have been a super weird party. The bridge where the crime took place eventually became informally and then formally known as the Train Robbers Bridge until a bunch of train nerds lobbied Network Rail to change it in 2013.

The Victims

Though the Great Train Robbery was praised as an unarmed and relatively nonviolent operation, the two drivers who were attacked that night would probably disagree, though you can’t ask them because they were both dead within a decade. Mills was 65 years old when he died of cancer in 1970, but he’d suffered brain damage and headaches for the rest of his life, and Whitby’s sister believes his death from a heart attack at 34 in 1972 was directly related to his trauma from that day. So that’s pretty shitty.

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