The Art of Train Hopping

Hi,

Thanks for all your feedback on last week's "The Bravest Person I Know". It meant a lot.

Today I'm very excited to share the chaotic story of an American train hopper ("There were moments where you get the most insane kindness, and then there's moments that are just so painfully cruel") – but first a few quick updates.

I developed the "He's The Devil" Webworm story into a podcast episode for Flightless Bird which is out today on all podcast platforms. Thanks for letting me tell it. It wouldn’t exist without you.

Alleged Assault by Michael Organ

Webworm heard from a number of people over the weekend about the subject of my 2022 documentary Mister Organ allegedly assaulting an elderly pro-Palestinian supporter at the local markets in Whanganui.

One witness told Webworm that Organ, “hit an elderly man multiple times after getting up in his face screaming.”

As previously reported here in August, Michael Organ is running in the local council elections in Whanganui, New Zealand. This probably shouldn’t come as a surprise in 2025. And given his history, this latest news probably shouldn’t be too surprising either. 

Video of the incident is currently with local police. Organ was allegedly heard droning, “Share the video! It’ll get me more votes!” afterwards.

As a sidebar, I’d like to give a shoutout to anyone in New Zealand continuing to speak out about the genocide in Gaza – especially considering the New Zealand government gives zero fucks about it. While the UK, Canada, Australia and others formally recognised the existence of a Palestinian state, the New Zealand government refused to do so. 

No wonder Organ feels it’s a good time to get into politics. 

NZ Media Council Upholds Complaint Against Radio New Zealand

The New Zealand Media Council (NZMC) has upheld a complaint against Radio New Zealand in regards to its coverage of the death of trans teen, Alex.

Webworm reported on RNZ’s problematic coverage back in June, writing: 

It was an extensive, detailed piece from journalist Ruth Hill — over 3500 words spelling out, in vivid detail, aspects of the teen’s life and eventual death due to anorexia.

It’s shocking to read personal details of a young person’s struggles, and death — but what makes all of this so repugnant is that the story isn’t really a story. It’s a thinly veiled piece of political advocacy, which uses the death of a young trans person to push an anti-trans agenda.

Thanks to RNZ, Alex’s identity and story has been erased, replaced with a fiction. Webworm knows this, because it has access to 6000 messages that Alex posted online in the year leading up to his death.

Following that Webworm story, RNZ dug in – changing a few aspects to its story but refusing to do anything particularly meaningful, like acknowledging the fact they’d received the story from an anti-trans group.

In their ruling, released today, the NZMC also took issue with that, writing:

The parents are entitled to express their views about the tragic events and their views on the teen’s gender identity and RNZ is entitled to report them. But their perspective came from a particular point of view and drove the narrative. The fact that the story was brought to RNZ by a group that is regarded as having an anti-trans perspective should have alerted RNZ to the fact that there was a wider agenda at play.

The NZMC concluded:

The Council believes RNZ should have been aware that there was a wider agenda at play and another side of the story that needed to be told, particularly when further information emerged after the publication of the first story. They could have provided a balancing alternative perspective in a number of ways, in the original story or subsequently.

The complaint is upheld for lack of balance and fairness.

Hopefully New Zealand’s public service broadcaster does better in the future. Although the words of RNZ’s Chief News Officer Mark Stevens to me, following my original piece, didn't bode well: 

“We understand that there will be differing views on our approach for this article, but we do not accept that we have a history of problematic reporting in this area."

And now onto today's main Webworm – about the dangerous, insane world of train hopping. This story takes place in the US, but it's an activity you'll find around the world. You just need a train.

It's a story I've wanted to tell for awhile, and I hope it gives a different perspective on what it's like to be unhoused. To put a face to people you may have seen, but not seen fully. I certainly didn't.

David.

The Art of Train Hopping:

"Ride trains? Like what? Like a hobo? What is this, the 1930s?"

"A lot of this story is going to involve, uh, drugs and alcohol," Simon Dragon tells me.

Simon reached out to me about a year ago, and I’ve been trying to catch up with him ever since – but it’s been hard to nail down a time. Or rather, it’s been hard to nail down a place, because up until recently he’s tended to be on the move. “My brother is being very awesome and diversifying his investment portfolio into real estate, so I'm going to live in a house," Simon laughs.

"If you would have told me when I was sleeping under bridges and hopping trains that one day I would live in a house… I mean, I don't own it, but like, you know, it's like being a homeowner. It’s fucking crazy, right?”

At 38-years-old, Simon is starting to settle down a little. But back when he was 26, he spent several years perfecting the art of train hopping. But to get to the train hopping, you have to learn about how he got to that point.

“I grew up in Lawrence, Kansas. Lawrence is like a cool little college town. There's a good music scene and the university is great. I went to college there, and I did graduate - despite being a pretty bad alcoholic. 

Substance use for me started pretty young. Like, I smoked weed the first time when I was 10, which is crazy young. And then I found out about alcohol when I was 15. I was trying to quit weed so I was, like, ‘Oh, alcohol, this is great. This is the opposite of weed. I actually want to do stuff and talk to people!’ 

And that pretty much became the trajectory in my life for a while – I started drinking almost every day.”

Simon tells me that after graduation, the alcoholism continued to the point where he burnt most of his friendships. “I was fucked off, like beyond belief,” he says. So he got out of Lawrence, moving to Portland, Oregon. And that’s when he met a girl.

“She had tattoos on her face. I was like, ‘This is fucking crazy!’ She intimidated the fuck out of me. There were just two lines that went under her eyes, sort of subtle, almost like a weird war paint type thing. Pretty cool in retrospect, as far as face tattoos go.”

Despite being intimidated, the pair got on and started sharing things about their lives.

“I was complaining about my job. I think I was delivering sandwiches for Jimmy John's on a bike, which is actually a pretty sweet gig because you're exercising all day.

But I was expressing my restlessness and all this and she was like, ‘You know you can just go out and hitchhike and ride trains and hold cardboard for money, and you don't have to work and you can kind of just do whatever?’ 

And I was, like, ‘What the fuck? Ride trains? Like what? Like a hobo? What is this? The 1930’s? Like, what the fuck? That's not real. Nobody does that!’”

I think that would be a lot of people’s reactions. An NPR piece from February stated:

The history of train hopping in the American imagination starts with hobos. Hobo culture was born out of economic necessity in post-Civil War America, when young men saw different parts of the country that they never knew existed.

A book called Riding the Rails also tackles the subject:

At the height of the Great Depression, 250,000 teenagers were roaming America. Some left home because they felt they were a burden to their families; some fled homes shattered by the shame of unemployment and poverty; some left because it seemed a great adventure.

By summer 1932, the 'roving boy' had become a fixture on the American landscape. The occasional girl was sighted, too, most passing unrecognized in male garb. They became known loosely as 'boxcar boys and girls.'

Riding the rails was a rite of passage for a generation of young Americans which profoundly shaped their lives. Self-reliance, compassion, frugality, and a love of freedom and country are at the heart of the lessons they learned.

That was all back in the 30s, and it’s never stopped. Except “boxcar boys and girls” are now generally now called “train hoppers”.

“When I say train hoppers, I'm really talking, like, ‘kids’. And we always call them kids, regardless of how old they were,” Simon tells me. 

“They usually wear all black. They have crazy tattoos. They might have a banjo or a guitar on them, or a dog. They're homeless, but they have a backpack and they look a little different than regular homeless people.

The main difference is that homeless people typically stay in a general area, whereas traveling kids – the whole thing is that you're always going somewhere.”

Simon and his tattooed girlfriend didn’t start train hopping immediately. They started with hitchhiking. As they hitched, they become more immersed in the world of “travellers” – the unhoused who are on the move. And Simon liked what he saw.

“The whole traveler community is alcoholism and drug use. It pretty much goes hand in hand with it. It’s part of the culture. It's just drinking all the time. So it was perfect for an alcoholic like me.

Anyway, we were living at this punk house in Portland, a fucking sick ass punk house called the 'Heretic House'. And I met some other traveling kids and we decided to go to sugar beet harvest.  

That was like the fork in the road: Because if we hadn't seen these kids, the trajectory of everything that happened afterwards would have never occurred.

Which is kind of another thing that's really bizarre about traveling – and makes it almost magical – there's moments like that where if you didn't take that one ride to get to that other place, you wouldn't have gotten that other hitch, that took you to that other place, and all this shit would have never happened.”

There’s a metaphor in here somewhere about the 136,000 miles of train lines weaving their way across the United States – paths diverging; paths crossing.

For Simon, those tracks led to him living in a punk house in Portland and meeting these kids who led him to the sugar beet harvest, where seasonal workers all converged to harvest fresh beets.

“We were in Fargo, and I think we worked sugar beet harvest, like, one day. And then we said, ‘Fuck this, let's leave’, which is something you can do when you're homeless. So we left and met up with these other kids that had a car. So then we were rubber tramping - that’s what they call it when traveling kids have a vehicle - and we drove down to Kansas city.”

And it was in Kansas city that Simon hopped his first train.

“So in the train yard, they have what's called the ‘siding’. And that's where when you enter a train yard the train has to stop for clearance to get out of the train yard. And that is where you catch the train. So it's stopped. 

Typically you want to catch it while it's stopped. It's kind of dangerous when it's moving, although that's what they call ‘catching on the fly’. And that's really cool. If you can do that, you're a bad motherfucker!

The first train that I ever hopped, it was rainy. We were drinking by the train yard. I had blacked out and was asleep next to the train.”

Suddenly one of the kids tapped on his shoulder and roused him from his drunken slumber

“So this first train we got was called a Cadillac grainer, which is slang, but it's basically a grainer that has an extremely deep porch. Like, I'm saying this is so deep that you can sit with like eight other people in it and you're completely unseen, which was extremely lucky for my first train.

But we soon found out that our luck was totally fucked, because we thought we were going south to an actual city, but the train just went to this bum fuck place called Parsons, Kansas, which is like nothing. 

And it stops off in this, like, basically a field. But yeah, that was my first train.”

And just like that, Simon had become a train hopper. He was addicted. Even if it ended in a quiet field it was more exciting than hitching, and more chaotic than rubber tramping.

Simon was unhoused and he was also happy. And money came easier than he expected.

“They call it flying a sign. And you've seen it, people with cardboard. There's a total art to doing that. And especially when you're traveling, the advantage you have over people that do it in the same city is that you're not recognized. 

And you go to places where there aren't a lot of homeless people. Like, flying a cardboard sign in a major city with a bunch of other homeless people is not good money. But if you're traveling and you happen to stop by Parsons, Kansas, and you go to an intersection or an on-ramp and your sign just says, ‘TRAVELING, BROKE AND HUNGRY' - which is the old standby that we used - people go, ‘Oh, you're traveling. That's kind of neat. You're not just a bum, you are traveling. That's kind of cool!’

And they give you money. And when you're an alcoholic and all you need is a handle of vodka, which is like 15 bucks, that'll get four people pretty drunk. So it's pretty easy to survive. And getting food is no problem. Like if you write, ‘TRAVELING, BROKE AND HUNGRY', you'll get fed so fast.”

One thing I am really aware of is that I don’t want to glamourise this. And Simon doesn’t want to either. To be clear - train hopping is illegal. And as Simon knows all too well, It’s dangerous. 

“Everybody's so fucked up so often, and also I think what adds to it is that while it is fun and great and awesome and you're free - you’re also homeless. You are sleeping outside. It is stressful. And so people I think have a lot of built up like rage inside of them. 

And I think in general a lot of times attracts violent people. So throughout my time being a traveling person, I got beat up. A lot of times I got stitches. I got stabbed one time…”

He trails off, so I ask him about the stabbing. “Actually it was my friend,” he laughs. “Yeah, we're not friends anymore.”

“We were both alcoholics drinking a lot. And this is what I was told, because I was blackout drunk. Apparently we were talking like we were going to fight, and I stood up to fight him. I came at him, and he just stuck me two times in the leg instead of fighting me. In retrospect, it's kind of bullshit because I'm not even good at fighting.”

There’s something I want to address at this point, and it’s how whimsical many of these stories sound when Simon tells them. Part of this is just due to his storytelling ability – but I wonder if it speaks to something larger about the train hopping scene.

Because it’s a scene built on riding these giant vessels that represent the American dream of freedom and exploration. The classic American story.

And I realise these 'kids' travelling these vast distances are forging and telling their own stories along the way. Many of these stories are violent, and they’re also objectively compelling. I mean, the Bible is the most popular book of all time, and it contains some of the most violent stories you’ll ever read.

I think of that moment in 2 Kings 2:23-24 where two bears maul 42 children just because they mocked Elisha’s bald head.

I digress here, but my point is that violent stories make for stories that get told and retold, eventually turning into lore – and I think so much of that plays into the stories told by train hoppers.

“A lot of traveling and the train riding community, you're sitting around waiting for the train so often that all you do is tell stories about other traveling kids. 

So this was like this was a huge story back when I was riding. There's two guys on a train - Dice and Scarecrow.

Scarecrow gets pushed off of the train [by Dice] while moving. He falls. Busts his teeth. Half his teeth get knocked out on the rocks, or the train tracks or whatever. He crawls on his elbows for five miles back to town. 

And this guy who gets kicked off the train, he's kind of like a big deal in the train riding community. Everybody knows him, right? And he's fucking pissed. And so he puts the word out that this guy who kicked him off the train did this to him, fucked his teeth up. 

And they got him. So they get Dice, and Scarecrow sees him and he's like, ‘I want my teeth back.’ And so apparently he had a mag light and a pair of pliers. And he's like, ‘I need my teeth back.’

And every time he would pull it and cry, Scarecrow would smack him in the head with the mag light.

I mean, this is like fucking brutal shit.”

It’s like something out of American History X or Pulp Fiction. Maybe it happened, maybe it didn’t – but I tend to think it did. Simon certainly thinks so, telling me he heard this story from multiple people with multiple perspectives. And like all depraved stories, it had a depraved twist.

“Later I was dating a girl who actually talked to the dude who had his teeth pulled, and he said that he didn't really even push the guy off the train - that he just fell. It's so fucked up.

So the whole thing is this weird dichotomy of ‘you're free and everything's cool’, but then you're facing that at any moment you don't know if somebody's gonna be especially crazy when they're drunk. Like, there are people that get murdered. 

I knew so many people that have died, like people I had rode trains with and that I'd hung out with." 

Simon rode on and off for several years, going to all the American states except for five. And amongst all the alcoholism, drugs and violence – there was plenty of beauty, too.

“One time we were in California and we're going north, and it was winding through the mountains really slow. It's creeping along this mountain and we look over and we see an old train that had fallen off of the mountain. It was just this skeletal old train, dead. And then it was like Mount Shasta in the backdrop. It was so fucking beautiful. It was like the coolest thing, like straight out of a movie. That was probably the prettiest moment.”

I ask him why he stopped train hopping; what snapped him out of it.

“Well, it would usually get to where it would just get really intense. I would suffer another serious injury or something. And then I'd have to recover. A lot of times I got stitches. I got hit by a car one time.

Usually my brother would come to my aid and be like, ‘Hey, come back and chill out.’ Cause like, you know, he doesn't want me to die and shit.  

I would be dead if it wasn't for him. He put me through rehab multiple times.”

Simon rode his last train about 10 years ago, but the few years he rode have stayed with him.

“It does stick with me, because when you are homeless like that, you're basically deciding to be the bottom of society. And I was willingly deciding to do that.

And so you see the absolute best and absolute worst in humanity. There were moments where you get the most insane kindness that is from the bottom of people's hearts. And then there's moments that are just so painfully cruel.”

Thinking of what we've talked about – from the adventure, to the violence, to the beauty and comradery – I wonder if he's ever tempted to return to his old life.

“Dude, when I drove here today from Kansas City, I drove under a train bridge and I saw two trains stopped and I looked up and peeped to see if any one of them were rideable. And I was like, ‘Yeah, damn, this would be nice right now.’ 

But yeah, I do always think about it. I mean, I could just take five days of PTO from my job and go do it. 

I was thinking about doing it with my friend who I still stay in contact with, but we were talking about it and part of what made it cool was that we didn't have money and we didn't have anything. So I feel like it would be weird to go into it with money because then it's like, what would the struggle be?"

He pauses for a moment, thinking some more. "But yeah, I do, yeah. I probably will do it again before I die, just for fun.”