Riding the Rails with Rick Telander

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For the past year, The Chicago Smokehouse has taken listeners through political debates, cultural detours, sports history, media criticism, and Chicago lore—but no conversation has landed with the sense of wonder, danger, and pure Americana quite like this one. In this episode, host John Howell asks his longtime friend and writing partner, the legendary columnist Rick Telander, to finally tell—in full—the story he has hinted at for years: why he rode freight trains across the American West as a young man… and what he found out there that he’s never been able to find again.

What follows is a portrait not only of a writer in formation, but of a country that no longer exists. It’s a meditation on literature, danger, romance, and the freedom that used to be accessible to anyone brave or foolish enough to go looking for it.

The Railway That Built a Writer

Before he was a columnist, before he was a celebrated author, before Heaven Is a Playground or the Sports Illustrated bylines or the Sun-Times columns, Rick Telander was a broke Northwestern student who believed—deeply—in the romance of American trains.

It came from childhood: the Rocket from Peoria to Chicago, a day with his father at a ballgame, walking the aisle between cars, eating sandwiches in the club car, and staring out the window at a country flying by.

“It was soothing,” Telander says. “The rhythm of the train—clickety-clack, clickety-clack—something about it just felt like freedom.”

That feeling grew as he read Hemingway, Kerouac, Henry Miller, and the Beats. Trains were not just machinery. They were a rite of passage. A test. A corridor to a different version of the self.

And so, sometime in the late 1960s, when he was young, strong, unencumbered, and deeply curious—he went.

Hobos, Yard Bulls, and the Rules of the Road

Riding the rails wasn’t nostalgia. It was strategy. Telander learned the protocols quickly:

• Never get on a stopped train. Wait until it’s rolling—slowly—and grab hold.

• Never stay until it stops. Jump off before it fully halts. The yard bulls—the railroad police—are looking for exactly your type.

• Find the hobo camp. Not the drifters, not the violent types—the hobos. “Hobos work,” Telander says. “Bums won’t.”

• Carry the right equipment. In Rick’s world, that meant a Samsonite suitcase—because in a boxcar universe with no chairs, having something to sit on can save your sanity.

These weren’t stunts. They were survival.

And in doing it, he discovered a cast of characters: true rail veterans, men who could read a yard map by the sound of a coupler snapping two cars ahead, men who could spot a westbound heading to California just by the graffiti on the grain cars.

One of them became Rick’s temporary companion: a real hobo with the unforgettable moniker Side Door Pullman Kid, born John Francis O’Connor—still riding the rails into his seventies.

“He was the real thing,” Telander says. “That guy lived a life most people don’t even believe existed.”

Fireflies, Pickup Trucks, and Tunnels of Smoke

The stories he tells are not jokes or tall tales. They’re sensory postcards from an America you can barely imagine today.

Near Dallas, riding an open frame on a hot summer night, he found himself in the middle of a light show nature never meant for human eyes. Millions of lightning bugs smashed into the steel around him, coating the car in flickering green light. The sparks drifted across his clothes. The air pulsed like a living lantern.

“I don’t think anybody had ever seen that,” Telander says. “You’d have to be riding a freight train in exactly that place at exactly that moment.”

In the Rockies, asleep in the back of a brand-new pickup truck chained to a freight car, he woke to the smell of smoke and unbearable heat—realizing, only too late, that the train had entered a long mountain tunnel. Diesel fumes filled the space. He couldn’t see. He could barely breathe.

“I thought I was going to die in there,” he says. “I didn’t know how long the tunnel was. It felt like forever.”

In Arizona, sitting on a grain car with a Mexican farm worker sharing a bottle of mezcal, the train was stopped abruptly by border patrol. The officers rounded up passengers car by car. Telander’s companion was taken off. Minutes later, unexpectedly, the man was brought back.

“He was a migrant worker,” Telander says. “They weren’t looking for him. But I’ll tell you—I had no idea which way that was going to go.”

A Detour to Literature: Anaïs Nin, Henry Miller, and the Journey West

Riding the rails didn’t stay separate from Telander’s literary ambitions—it shaped them.

As a young freelancer for the Chicago Sun-Times’ old Sunday magazine, he was sent to Milwaukee to interview Anaïs Nin, the diarist, writer, feminist icon, and sometime lover of Henry Miller. She was elegant, soft-spoken, luminous, and nothing like the angry revolutionary the audience expected.

She liked Telander. She sent him her books. They wrote letters.

And then—because he was young and broke but completely serious about literature—he asked if he could visit her in California.

She said yes.

So he did what he knew how to do: he grabbed his Samsonite, found a freight line heading west, and rode to Los Angeles.

There, on a beach under a lifeguard stand in Santa Monica, he slept. During the day he visited Nin, toured her home, even snapped a photograph of her beneath an original Vargas painting.

He asked if he could meet Henry Miller.

She phoned him.

Miller—very old, living in Pacific Palisades, frail but lucid—remembers Nin fondly but is too ill for a visit. The meeting that Telander risked his life for wouldn’t happen.

“But I understood it,” he says. “I knew he was old. I knew the world was changing. And she comforted me… in the way a woman can.”

John Howell interrupts:
“Comforted you?”
Telander smiles.
“We had a respectful relationship,” he says. “Leave it at that.”

Freedom, Then and Now

The conversation doesn’t stay in the 1970s. It turns philosophical fast.

Telander talks about how freedom has shrunk since then—how the ability to disappear, to be unreachable, to exist in a town or a field or a train yard without anyone knowing, has evaporated.

“We traded freedom for convenience,” he says. “And we did it willingly.”

Phones. Apps. GPS. Pacemakers that report your heartbeat to the cloud. Ring cameras mapping the neighborhoods. Satellites that see through clouds. Drones hovering over backyards.

“You cannot hide anymore,” Telander says. “It’s impossible.”

Howell, who once feared the government implanting chips, laughs:
“We chipped ourselves.”

“You Need to Write the Memoir”

For perhaps the first time in their partnership, Howell is the one urging, insisting, almost pleading:

“Rick—you have to write this. A book. At least 125 pages. Something. You have the stories.”

He’s right. The stories are wild, funny, dangerous, tender, and unmistakably American.

And Telander?
He shrugs. Laughs.
Maybe he will. Maybe he won’t.

“My life is in my books,” he says. “In the columns. In everything I’ve written. If somebody wanted to piece it all together, they could. I don’t know that I need to go back and relive it. But I don’t mind talking about it.”

And that’s what this episode gives us—something Telander has never written, never published, and rarely discussed in full.

For one hour, he relives it.

And for one hour, we get to ride along.

A Closing Note on the Samsonite

Somewhere amid the danger and nostalgia, Howell remarks that Telander’s story is “the greatest Samsonite commercial never made.” In a world where luggage is now marketed with influencers, unboxing videos, and airport glamour shots, there is something perfect—almost comic—about a battered suitcase surviving tunnels, deserts, tunnels, fireflies, border patrol, and the back of a 1971 Ford pickup chained to a freight train.

It never broke.
He never lost it.
He never lost himself, either.

But he did lose something—something all of us lost: a kind of American freedom that feels mythic now.

And that is the real story of this episode.