Trying to understand freight riders’ desperate freedom


Library of Congress

A classic image of train-hopping teens during the Great Depression.

“Bums,” they called them. “Lazy trash,” they said.

I was standing at a railroad crossing in downtown Billings during a frenzied street dance when a slow-moving train passed by. Three modern-day hobos sat in one of the box cars—two young men and a young woman. The businessmen and women standing next to me that June afternoon apparently couldn’t help but comment to one another, as if reassuring one another that their lives were superior.

“You know what? I’m calling the rail office at Montana Rail Link,” said one of the men.

“Don’t be a jerk,” I said. My interjection was met with confused looks. “They’re not hurting anyone. Just leave them alone.” In that second, I became something of a pariah. The group I was standing among separated from me, and began talking quietly among themselves.

Growing up, I had an uncle who was, by his own definition, a “professional hobo.” Uncle Posey (Don) had grown up in depots around Montana and Wyoming where his father—my grandpa—worked as a station agent. Uncle Posey hopped his first train in the 1960s. He was 12 years old. Ultimately, my grandpa had to go to Chicago to retrieve his son. I’m sure my grandpa wasn’t thrilled, but that was Uncle Posey’s introduction into the world of riding the rails. I asked him one time how he settled on the lifestyle that defined him.

“The trains were always rolling by,” he said. “It was something that you didn’t have to ask for or buy. If you needed to get going and didn’t have money or time to make some money, you could just hop right on and go. If you know what you’re doing, it’s no more dangerous than riding a bus.”

Uncle Posey was “that guy” that most every family has: unfit to fit in, too smart for his own good, in and out of jail and prison throughout his life. He did time behind bars in the early ’70s. According to my mom, my grandma let out a sigh of relief when he was incarcerated. “I finally know where he is and that he is safe,” she’d said.

The life of a hobo (or freight-hopper, or rail rider) has an undeniable appeal to me. East of Billings—my home for most of my life—both sides of the Yellowstone Valley are lined with railroad tracks. The sound of the trains laboring in the distance is the white noise of my life, and waiting on trains on a daily basis has become a thorn in my side. Over the course of my life, I’ve lost countless hours at railroad crossings.

But those moments did more than just teach me patience; it was there, waiting, that my interest in both graffiti and hobos took root. Where else but alongside the railroad tracks could an Eastern Montana hayseed come face to face with dazzling graffiti from inner city Chicago or Detroit? Not that it’s the life I want to live. It’s more a lifestyle I am compelled to try to understand. Maybe it’s because I grew up next to endless miles of railroad tracks, all leading to places I wanted to go. Maybe it’s because of my Uncle Posey.

Or maybe it is because of Lyle Crowley, known as “L-Train” to his freight-hopping brethren.

L-Train’s path first crossed mine over a decade ago. He was flying a sign on the corner of 27th Street and Sixth Avenue in Billings, and my friends and I were about the desperate business of buying liquor for a party at the flop house we called home. Since none of us had hit our 21st birthday, and since L-Train sure as hell looked a far sight older than that, we hit him with a “hey mister” proposition. It worked. He picked up the fixings for our party and even returned the leftover change. In exchange, we invited him to the party.



In this still from the documentary “Freeload,” a young train rider catches some fitful sleep.

He showed, then stayed. Lyle crashed on the couch for a couple of weeks and regaled me with tales, probably half-true at best, of riding the rails. He explained “the law of adverse possession” as it pertains to freight-hoppers (read: “squatter’s rights”) which states, essentially, that everything under creation intended for use belongs to no one if it is not actually being used. L-Train was only 24 at the time, but looked closer to 35—his skin cracked and baked, his hair thinning, a glossy eye from “the last lesson he let his old man teach him.”

Today, L-Train is just regular old Lyle. He lives and works in Topeka, Kan., with a wife and two (soon to be three) children. Billings ended up being the last stop of his hobo travels. He took a job framing houses, and by the time he left town, he was driving truck, paying taxes, and had a 401k. He and I keep in touch, albeit on a highly irregular basis. However, when I began searching for a way to shed light on this almost invisible subculture, I knew I would have to give him a call.

“Hell, I was born into the worst situation you could imagine,” he said when I asked how he came to ride the rails. “My old man was brutal in a way most people could never understand. I hit the door running when I was only 14. We lived next to a set of railroad tracks in the U.P. of Michigan. I used to hide from my dad when he was on a bender, and I’d watch those trains loaded with cars go rattling by and daydream of all of the better places that they were headed.

“Finally, one day right before I turned 15, I had enough. I stole a pack, sleeping bag, and 300 bucks from my old man. I waited for a train to slow down in a big curve in the tracks outside of town, hopped on, and never looked back. I was on the rails for 10 years before I met you guys in Montana. I had never looked back at the life I left behind, but it wasn’t until then I started looking ahead, and started thinking about a life after riding.”

It may be hard to imagine that a life of listless wandering and eating scraps from back alley trash bins could be liberating. The fact of the matter is, we are actually incapable of buying out of the modern paradigm of American existence. Trying to buy your liberation from society is oxymoronic: the greater your purchasing power, the more deeply entrenched you become in the system. You can’t buy your way out; you simply have to opt out. You have to stop playing the game right where you stand. When you stop worrying about your credit, your debt, your retirement, your health insurance, or your career, you realize that liberation is already at your fingertips.

But this comes at a cost—a cost all too familiar with any freight-hopper who has spent much time on the rails.

Living above or below the law is dangerous. You still have to fight for everything you have, but there is no assurance of ever having anyone to help you keep it. It is a dog-eat-dog world for people on both the inside and outside of society—except that those on the outside must rely solely on their intuition and “street smarts” to survive. Even a subsect of society, no matter how chaotic and anarchistic, is still, in and of itself, society. No matter how wild or seemingly lawless they may appear, all societies have rules.



In another still from “Freeload,” train riders look for a likely berth.

Established at an early hobo convention in the late 1800s, the Hobo Code of Ethics exists to this day. The Hobo Convention itself has been held on the second weekend of every August since the late 1800s, in the town of Britt, Iowa. Now organized by the local Chamber of Commerce, it is the largest gathering of hobos, rail-riders, and tramps, who gather to celebrate the American traveling worker. It was there, at an early convention, that a code of ethics was established. It is a basic a code of behavior: don’t steal from other hobos, don’t hurt kids, and don’t ruin it for the rest of us—that kind of thing.

Less intuitive is to whom the Hobo Code of Ethics applies, as not all who ride the rails are so easily categorized. For instance, when I asked Lyle if he’d considered himself a hobo, he said, “No, not really.”

“Hobos,” he explained, “in the strict sense, are people riding the rails looking for work. It’s a term from the Great Depression. Hobos had a code of ethics, and that was pretty well known back in the day. I think it is why they were accepted, or maybe just tolerated more. I took work only when I needed it, and I didn’t need all that much.”

According to the great critic and linguist H.L. Mencken, the difference in terminology goes something like this: “A hobo … is simply a migratory laborer; he may take some longish holidays, but sooner or later he returns to work. A tramp never works if it can be avoided; he simply travels. Lower than either is the bum, who neither works nor travels, save when impelled to motion by the police.” By those definitions, many of the people we would refer to as hobos are, in fact, tramps—including Uncle Posey and Lyle.

Several times in my quest to shine light on the train-riding subsect of American culture, I was advised to watch “Freeload,” a 2014 documentary made by Montana filmmakers Daniel Skaggs and Ryan Seitz, a native of Billings.

“Hobos, to me, represent an American pastime—a story told through the lyrics of Woody Guthrie and writers from the Dust Bowl era,” Skaggs said. “Historically, men of the Great Depression rode trains out of necessity. I, however, had been riding freight trains for nearly a decade seeking adventure. The times have changed over the years, and our documentary tells the story of the modern-day rider.”

In the summer of 2011, Skaggs, equipped with his camera and a pack and a vision, hopped a freight train out of Missoula. “I crisscrossed the nation’s railroads encountering the characters of this documentary,” he said. “Rolling through countrysides and cityscapes, I spent my days living on the streets interviewing train riders. Underpasses, boxcars and abandoned buildings became my living room.”

The film highlights the strong sense of camaraderie among the present-day hobos. They share what they have, including the company of others.

“Over time, I gained acceptance by the brothers and sisters of the road,” Skaggs said. “Because I was not an outsider, the characters of ‘Freeload’ could tell me their stories without inhibition. They truly opened up on camera and welcomed me into their lives.”

As far as human interest documentaries are concerned, “Freeload” is as compelling as you can find—it’s personal, it’s raw, and it’s very, very real. It chronicles the lives of roughly five train-hoppers and their trials, and doesn’t approach train-hopping as a topic, but rather as a personal experience of subterranean culture.

The cast is compelling: “Blackbird” is a lost teenager searching for the answers to life; “Ponyboy” and “Rachel,” two young lovers, attempt to settle down in Texas but are lured back by the freedom of the road; and brothers “Skrappe” and “Christmas”—separated most of their lives—try to rekindle their lost brotherhood.

These real-life freight-hoppers, modern-day tramps, bring to the screen stories of love, struggle, adventure and family, but, perhaps most importantly, they illustrate the humanity hidden within each and every person—whether they are riding the rails or looking on in disgust from a downtown Billings railroad crossing.

In the film, Skrappe observes modern society through the lenses of the liberated freight-hopper. “The definition of insanity is doing the same thing over and over while expecting different results. That is what having a job is. That is what having a house is,” he explained. “The road is my job. Holding a sign is my job. Riding the rails is my job.”

But my question is, if this his “job,” then to what end is he working? What results does he expect to see from a life spent clutching the back of a freight train? The same vein of logic that compels Skrappe to dismantle society at large can just as easily be turned and used on the life of a train-hopper.

Seitz, who wrote and edited the film, put it this way: “Initially I found myself really respecting their idealism. I found myself agreeing with them. I mean, there I was sitting with 40k in student debt, stressing about my future, and then, bam! There are these kids…at first, I thought, ‘Man, these kids have it all figured out.’”

But that veil began to slip the more time Seitz spent editing hours and hours of footage.

“After a while,” Seitz said, “I began to see everything that goes on in that lifestyle—the drama, the addiction, and so on. As much as they want to be blazing their own trail, they are actually just conforming to a culture of its own. They all wear the same ‘uniform,’ they all have to drink Steele Reserve, they all have to have a shitty face tattoo or someplace really visible, like a badge of honor.”

Without question, all of the train-hoppers, hobos and tramps I’ve met in my life are running from something: their pasts, the law, their families, their futures, or even themselves. “They’re all escapists,” said Seitz, “running from something worse than what they’re running towards.”

When my Uncle Posey hit the tracks for good in the 1970s, he was running away from a lot. My grandpa, the train agent, was a real piece of work, cut from the same cloth as Lyle’s dad. They were men running from crises, but who found more of the same everywhere they turned. Lyle, but by the grace of God, found a balance right around the time we crossed paths. He got his life straight, but, even in his own words, “guards against the past” to this day. He had nightmares he isn’t yet willing to talk about.

Uncle Posey wasn’t so lucky. Story goes, he was well into his 50s when he got clubbed and left for dead on the side of the tracks in North Dakota. He came to in the hospital to find that large portions of his feet had been amputated. Either he was mugged or passed out drunk. Regardless, he pissed his pants and froze solid to the ground. His train-riding days were all but done. He drank himself to death over the next 10 years.

As I was hanging up the phone on Sietz following our extended conversation, he observed: “Isn’t it interesting how these kids go about seeking opportunity in ‘The Land of Opportunity’?”

Despite the bad-luck existence of Lyle, my uncle, and the kids from “Freeload,” I find myself no shorter on empathy for them. You don’t get to pick your parents—you don’t get the luxury of choosing what opportunities are available for you during those crucial, formative years. Lyle didn’t get to choose, my Uncle Posey didn’t, Skrappe didn’t. If my dad had treated me like a punching bag, I probably would have done whatever I could to get free.

It’s no different than a fox chewing off its leg to get out of a trap. Because of that, I don’t look away. I don’t talk shit when I see kids clinging to the side of a train barreling through Billings. I don’t call the yard office. I try to put on their boots. I try to see the world through their boxcar doors. I try to understand.

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