The Homeless Painter

I’m a painter, he said, with eyes filled with serene humility. I thought he meant a trade painter, like for walls in houses. I barely registered a potential second meaning. But about 10 minutes after walking into the shelter with me, The Painter came up to the front desk with a two foot by three foot canvas to show me.

His painting was masterful. It was a city skyline, in neon pink and yellow that blended together in proud skyscrapers. These bright beacons were contrasted against the dark blues of water in the forefront. Sailboats seem to glide in the water. It was painterly and choppy, and looked like something Monet would have approved of.

I asked him if it was Chicago, because of the city’s proximity to water.

No, he told me, I wanted it to look like it could be anywhere.

We both escaped for a moment through art, and came back hard to our reality. Homeless shelters are not bastions of beauty. People do what they can for the homeless with what they have, and in that aspect, it’s a gorgeous sight. But the innards of shelters are muted, dull, and prison-like. The doors close by 5 p.m. People who get beds are free to leave but that leaves others free to take their bed. Fits of coughing can be heard throughout the year — someone is always sick. There is nothing on the walls, because if someone can benefit from taking something and selling it, they will. Art is not a priority.

Did you ever want to do anything else? I asked

Nah, he said. God made me a painter, so I’m a painter.


Poverty changes the brain, in ways that neuroscience is only beginning to understand. Operating under unrelenting, hopeless, back-breaking scarcity causes toxic stress. Synapses start to rewire when toxic stress continuously overrides the system. Crisis becomes the new normal.

The homeless live, eat, sleep, and sometimes perish in this new normal. Their perpetual state of crisis has permanently changed their brain architecture, yet a lot of those who work with the homeless would say it is no real excuse.

People do not have the right to the cards they think they should have been dealt, I’ve been reminded time and time again.

When I am volunteering on Monday nights, I find the limits of my compassion tested. I feel bad that the problem of homelessness exists in our society, as it is a terrible way to live. It’s animal-istic and dehumanizing. They seek independence but are not granted it at the shelter. I don’t always feel bad for each homeless person, as I have been called a cunt for not being able to answer questions quickly and shouted at out of anger. I try not to take it personally, but I can’t help it. Some of it starts to sink into my skin.

I start to look for The Painter every Monday night. I’m embarrassed because he introduced himself before he showed me his painting, but I forgot his name. I nickname him Caravaggio, after my favorite painter.

The more I see Caravaggio, and the more I am exposed to the depths of homelessness, the more I find him fascinating. He’s always calm and seemingly quiet. He never needs anything. He’s unlike the rest, who either flirt with me or curse and dismiss me for not always being able to provide them what they need at the exact moment. Caravaggio always seems to be in is own world, always wearing a t-shirt, shorts, and sandals.

Every now and again, I am able to catch him as he floats in and out of the building. I have so many questions about his process.

How did you become a painter?

What do you paint?

How do you manage to paint at a shelter — like logistically?

Where have you sold your work?

Every Monday night, my answers slowly trickle in as I catch him here and there as he moves about. He speaks with a slow cadence, with rich elegancy and never over a hushed tone.

I was born a painter. I’ve always been good at it.

I paint what’s in my head.

I paint at the Stewpot, the homeless ministry.

I’ve sold my work here and there.

One night, after a particularly long two hours of stamping mail, I walked out to my car and saw Caravaggio on a smoke break.

Paint anything recently? I holler out to him.

In my mind, he said. Every day.


Consistency is key.

As trust between Caravaggio and I builds, I dive deeper. I find out his real name and I found his story similar was to my father’s. A descent to homelessness can happen pretty quickly.

Edwin was born in Omaha. His family moved to Colorado when he was 8 years old. Edwin and I bound over our love for Colorado, and have the same observation about the winters there — they’re harsh, but bright. Anything feels possible.

He went to the University of Colorado with the intent to be a journalism major, but he quickly lost interest. His passion was art, and he ended up switching majors.He admitted to me that a certain Teacher’s Assistant in the art program compelled him to take his classes seriously. “Everything just made more sense when she said it,” he gushed over his 30 year old crush.

After college, he went into the Navy. After completing a portrait of his superior officer, word spread about his talent. He quickly got commission after commission of various naval officers, and eventually worked his way up to doing a portrait of an admiral and his family.

From there, he worked a series of odd jobs in the restaurant industry. One evening, he lifted a heavy keg and felt blinding pain in his back. He awoke in an ambulance, and x-rays revealed a herniated disc. He was left to mend but his absence at work did not go unnoticed. He was fired. Injured without the prospect of getting another job, he quickly lost everything in his name.

He wound up in Dallas, with the assistance of a bus pass. He tells me with a smile that he feels like he’s slowly dying here. It’s too hot, he says.

He has no desire to go back to the restaurant industry and considers his injury one of the best things that happened to him. Every day, he gets on the bus or walks to The Stewpot, a local homeless ministry that has an art program for the homeless. He paints from 9 in the morning to lunch, then comes back and paints to the Stewpot’s closing. He does not paint when he’s at the shelter any more, because he finds people’s questions annoying. When he has his easel out, people come up to him and ask him what is he doing. Tying my shoe, he tells them.

God made me a painter, so I am a painter, he reminds me.


I start to bring Edwin books about painting. We start to talk about my own attempts at art, which are futile. But he’s always encouraging. I show him a photo of one of my paintings that looks like split pea soup, and he studies it for a moment.

There’s a market for this, he says.

I roll my eyes. Get out of here, go back to your bed.

He laughs, and then he asks me something unexpected — would I go to his art show.

Will there be wine? I ask.


Then yeah, I’ll go.

He smiles, with that same serene humility of his. I think he knows I probably would have gone regardless.

I spent a year and half of my life in the “art world” as an art museum tour guide and assistant. I always felt like an outsider, because art shows attract the wealthy and are intensely elitist. I do not go back to that world unless I am compelled, and in this moment, I felt compelled.

In the faintest of drizzles, I drive over to a Methodist Church that is in the resoundingly, unabashedly rich part of town. An elegant staffer in a suit holds the door open for me as a close my umbrella. As I walked through the hall to the banquet, gorgeous stained glass was muted by the overcast clouds.

I edged myself around the room, doing a once over of all the paintings on the wall. Some of these paintings were quite good, others were probably going to stay on the walls. The hall was filled with tables of salmon spreads and cheese plates. It was a splendorous sight to see.

From the opposite side of the room, I can spot Edwin’s paintings. His style is distinct. Thick, heavy brushstrokes just oozing with paint and playful use of color. In lieu of lacking my own discretionary income, I try to talk another woman into buying one of his works to no luck. But as I walked around, I was overcome with melancholy.

He isn’t here, I realized.

He probably couldn’t afford to come. The public transportation system didn’t reliably take people from the shelter to this church, over 20 miles away. He wasn’t going to get see his show.

The reception was a sobering reminder of the business side of art, leaving the wealthy to be patrons of, in this case, literally starving artists. Those thoughts permeate, and mull in my mind as I drove home, past the mansions of Highland Park.

Yet, I come back to Edwin’s words, God made me a painter so I’m a painter, and I feel better. He’s happy. It’s okay, I tell myself.

That night when I got home., my melancholy dissipated even more because I looked up what his name means.

Edwin is Old-English for rich friend.

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