Stuff You Should Know
SYSK’s Fall True Crime Playlist: How The Great Train Robbery Worked
26 Sep 2025
Chapter 1: What is the main topic discussed in this episode?
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Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google doc and send me the link. Thanks.
Hey, just finished drawing up that quick one page business plan for you. Here's the link.
But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the iHeartRadio app or wherever you get your podcasts.
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Chapter 2: What is the Great Train Robbery and why is it significant?
one of the crimes of the century in England for sure. I mean it was huge in the press and these guys that knocked off this train became these kind of weird working class heroes. Well one of them became the symbol for the anti-establishment. Which one? What was his name? The one who made off for years and years.
Oh, yeah, yeah.
Biggs. Yeah, he was on the lam for like 30 years, so he was super famous. Yeah, and they knew where he was, and they couldn't get to him, which we'll talk about, but he became like this folk hero of the anti-establishment. He sang vocals on lots of punk records.
Oh, really?
Yeah. Yeah. Yeah, I saw in both documentaries, they had a bunch of interview, like on the street interviews from the time, like with regular upstanding citizens, like whose side are you on? And a lot of them were like, well, I feel ashamed to admit this, but I kinda think these guys really took it to the cops on this one. And they thought they were ingenious.
even though the plan as we'll get to really was pretty uncomplicated yeah it wasn't nearly as clever as it was made out to be right well let's talk about the plan so there was this idea who had who had the idea the original idea I believe his last name was Fields.
He was the guy who originally had the idea and approached several people, criminals, for partnership, and they all turned him down except for this ace safecracker by the name of Goody. Okay, so Goody had a friend who was, his name was Bruce Reynolds, and I guess he originally funded the whole thing? Yeah, well, they were in a gang called the Bowler Hat Gang in London. I know, right?
I don't think we've said this. We've made reference to the Wild West and train robbers and everything. This is the 1960s. Yeah. Like the early 1960s that this is going on.
Yeah and the bowler hat gang was, they dressed in bowler hats and suits and they had done some crimes and they were mainly career criminals and they actually even, they had the press's attention and they actually tried to rob a train at first but it didn't work so well and they got away. But they had sort of a, not a trial run but they legitimately tried to knock off another train.
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Chapter 3: How did the robbers plan the Great Train Robbery?
We know that they're within a 30 mile radius and we're gonna start canvassing the area. They get word of this. They're within 28 miles. And they go, well, crap. they're gonna find us. And they also said it was sort of a city boy's move to think you can hide out in the country like that.
And this one guy in the documentary was like, no, out in the country you get noticed if you're 15 guys in a farmhouse. That was their undoing. A neighbor said, there's a lot more people at this old rambling old farm, and they're all wearing bowler hats for some reason, or at least half of them are. Yeah. there's something fishy going on.
So when the word got out that this train had been hit, this guy came forward and said, you guys should go check this farm out. Well, the guys weren't only at this farm for the half hour after the heist, they'd been there for like eight days, waiting for the day to come, getting ready, eating things that required ketchup, playing Monopoly. Yeah. Played a lot of Monopoly with their real money.
Yes, they did.
I guess they thought that was just a fun thing to do. Hilarious. Yeah. And they did go to the trouble of wiping down a lot of the stuff, but they left a lot of stuff behind, including the Monopoly game, including the ketchup bottle, and a lot of other stuff that had prints on it. Well, yes, because Fields was supposed to get a guy to go torch the place. Yeah, that's what I thought.
I was like, why wouldn't you just burn the place down? That was the plan, and apparently the guy never did it, and they ended up getting out of there a few days early. They left five days into it because they obviously heard the news that they were canvassing the area.
So they left quicker than they wanted to, and like you said, left a lot of stuff behind because they thought it was going to be torched. Their plan was to lay low there for a few days? Yeah, to keep laying low. But when they found out they were basically making their way to them little by little, they got the heck out of Dodge quicker. Well, that probably kept them from getting caught sooner.
Yeah. So the public is being treated to this incredibly daring train heist. These people got away without a trace for at least the first week. Finally, within a week, this Leather Slade Farms has been identified as the place where these guys were hiding out. Yeah, they found the trucks. And they got at least one person within eight days of the heist. And all of a sudden, people start falling.
There's 15 people. And on the case is called the Flying Squad, who are like the best of the best that Scotland Yard has to offer to combat some of the best of the best criminals that Great Britain had to offer at the time. Yeah, Chief Superintendent Detective Tommy Butler was the head of the Flying Squad. And like you said, this was so sensational because it was the top robbers and the top cop.
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