11/19/2025
Life on the rails
By Joe Arce and Corey Crable
In depth report
This is the first part of a two-part series!
Rupert Aguirre doesn’t mind if you call him a hobo, it is part of his own life history.
Since the late 19th century, the stereotype of the hobo as a lazy vagrant looking for handouts from society has pervaded American culture. But Aguirre says the hobo has his own culture – one that has been studied for more than a century, opening a window into a subculture that even has its own convention.
Aguirre says he wants to spread awareness about life as a hobo, and he has done so in the form of a manuscript, as well as serving at the keynote speaker at the National Hobo Convention this past summer in August in Britt, Iowa.
“I want to tell people about the hobo community. It’s unlike the bums or the tramps, which don’t travel or work,” Aguirre says. “But the hobos, they live in a community, and they travel and they work and they contribute to the community like a family does.”
Aguirre’s story began in 1961, when, at the age of 16, his father died. Aguirre says he was consumed by grief – to an extent that he knew he had to change his surroundings so he could heal from the loss.
“When he died, I told my mother I couldn’t live anymore in the same house. I had so many memories of him. So she said she was going to call my brother Johnny in Chicago to send me a train ticket,” he recalls. “But instead that same morning, I got up at 5 o ‘clock in the morning, made a couple of sandwiches, and I hitchhiked to Chicago.”
For the boy everyone called Ruperto Jr., Kansas City’s Westside neighborhood was no longer home. When he arrived in Chicago, Aguirre says he lived with his brother for four months, directionless in life and still hurting from the loss of his father. Eventually, he and his brother fell into arguments, and Aguirre decided to leave. It was two weeks before Christmas, and Aguirre was alone on the frigid streets of the Windy City.
In those first nights alone, Aguirre called out for help. To his amazement, an angel appeared.
“I was praying to my God in a dark alley. I was praying to my God to take me,” he says. “And a woman, she got close to me, and I said to her, ‘Are you the Our Lady of Guadalupe? She said, ‘Oh, no. I just came. I heard your cries for help.’ And so she helped me. She helped me around the corner, to a Christian Reading Room. And there they helped me out. They sent me to a homeless shelter. I’d stay there for a day or two. I came back and I told them that I would like to talk to that lady that saved my life. They said, ‘No, we don’t know any lady like that. So that was maybe a vision.’”
Despite the uncertainty of the world around him, Aguirre knew in his heart that he could meet the future with bravery, no matter the circumstance – he decided to embrace the unknown and began train-hopping across the country, finding work where he could and meeting others who became not just mentors but also cherished friends. Aguirre spent the next five years living as a hobo.
“It was 1966 when I jumped off my last train,” Aguirre says. “I was en route to Tucson, Arizona, so somehow I took the wrong train, ended up in El Paso, Texas, where I met my future wife Esther. So that was the last time.”
Aguirre married and started a family, setting down roots after what had felt like a lifetime of spending nights in new cities around the country. He and his wife had children, and Aguirre says he’s never kept his past from them – in fact, he notes, they respond to his stories with interest and curiosity.
“My wife, and everyone else, they tell me, ‘All right, we heard it before.’ But then I have my son, Chris, he’s always asking me questions. ‘Dad, what happened here? What happened?’ And when I try to explain to him, he says, ‘And then what else? And then what else happened?’ So he (finds it) very interesting.”
Chris told Hispanic News he’s always been fascinated by his father’s tales of life on the rails – that, in fact, they have guided the course of his own life in his work in the medical field, allowing him to embrace his dad’s fierce spirit in the face of adversity. He’s learned the importance of community, too.
“I’m very proud of him. I know people may just have a misconception at first and hear the word ‘hobo,’ but if they really learn about it and understand it, then they’re like, ‘Oh, that’s unique,’” Chris says. “I never knew they had their own community and everything else until years back when I learned about it. Then I started doing some research. I’m like, ‘Wow, these people really still treasure traveling, and certain people that have that lifestyle, they take care of each other. And that’s exactly what it is. It’s a lifestyle.’”
Chris says that thanks to his father and his knowledge about the hobo lifestyle, he does his best to help others.
“Whenever I do see people, I don’t know what their situation is, but I do help them out. You know, I’ll give them some money here, or I give some of my coats to people that I’ve seen walking around, stuff like that,” he says. “So it made me change my view of people in general, that there are people that are good. There’s good in this world. And there’s so much negativity and all this stuff going on around the world and in our country. We need something good, something that can inspire people, and to help people.”
It hasn’t been only men who have acclimated to the hobo lifestyle, Aguirre adds. During his time as a hobo, he met women and children, too, living that same life.
“I’ve seen a lot of women, and mostly I’ve seen kids. I was 16, and basically I saw kids that were younger than me -- I would say 15 and probably some 14. But the thing about it is that a lot of these kids, they had a hard time too, worse than me, because nobody would help them, until I would help them. And it’s a struggle all the way around,” he says.
That struggle, Aguirre says, always seems to melt into the background in those quiet moments when the beauty of nature reveals itself and hope springs anew.
“You have to survive every day, and there are struggles, but there’s some great times,” Aguirre says. “I mean, the most beautiful scenery and sights that the great Lord gave you -- you’re by yourself watching the beautiful mountains and streams and rivers.”
And as Thanksgiving nears, Aguirre prepares to spend the holiday with his growing family – the people for whom he gives thanks every single day.
“Thanksgiving means so much to me, for having the family that I have now. I will be married 60 years. I have three children. I have one grandson, 10 granddaughters, and three great-grandchildren. And if it wasn’t for those people that saved my life, I wouldn’t have been here,” Aguirre says. “It’s been like nearly a half a dozen times when people saved my life. And this is why I’m so grateful, especially during this Thanksgiving week.”
Aguirre says he hopes that his speeches given at hobo conventions and his manuscript clarify some misunderstanding about the hobo lifestyle and give people an appreciation for this special subculture.
“When you see a rail rider hobo, riding atop a speeding train, remember that they are indeed a special breed of people that respects life and living and longs to return Homeward Bound again,” Aguirre writes, “to the jungles where life is worth so much more."
Part II of this series next week will continue the story of Rupert Aguirre’s life and his role at the annual National Hobo Convention.
