Talented Homeless Man Sells His Paintings To Support Himself And Inspire Others

In September, Jon Masters of Pensacola, Florida, was homeless and had just been released from jail on a trespassing charge. The boat he had lived on with his companion and medical alert dog, Sheba, sank, so he temporarily gave her up to an animal shelter.

When he got out of jail and picked up Sheba from the shelter, Masters stood on a street corner with a sign for three days until he had $40—enough to buy canvases, cheap paint and paintbrushes, according to the Pensacola News Journal.

Masters began painting eerie landscape portraits and selling them on the side of the road to make money. “I’m just trying to get some money together,” he told the News Journal. “I’m not trying to be the homeless guy with all the problems. I have a little talent for painting, and that’s what I’m trying to do to make it by.”

But then the paintings started selling as fast as Masters could paint them, and the Huffington Post and USA Today picked up his story. Now, his paintings are in high demand in Pensacola, and other homeless people are starting to make their own small-scale, craft-centric businesses at Masters’ teaching.

The epelelepsy research foundation just came and got my painting. (Sniff Sniff) another baby off to find a New home.

Posted by Jon Masters on Monday, October 12, 2015


“That’s what I enjoy the most,” Masters, 56, told USA Today from his oak-shaded spot next to Navy Boulevard in Pensacola with Sheba at his side. “I’ve got other homeless guys coming up to me to check out what’s going on. They’re hearing about my story from other homeless people. They’re seeing the response I’m getting and some of them are trying to figure out what they can do that’s similar. They want to know how I learned to paint. They want to do something on their own. I’m actually able to inspire others. To me, that’s the best part about all of this.”

Masters, which is his pen name and what Pensacola residents know him by, learned to paint while living in New Orleans and studying artists in Jackson Square. He also told USA Today that he watched a few YouTube videos. He saved up enough money in New Orleans to buy a very used sailboat, and, tired of the competition in Jackson Square, decided to sail east and then south.

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He and Sheba lived on the boat until they reached Pensacola Beach, where Masters said he was arrested on a trespassing charge that was actually more of a misunderstanding that arose when law enforcement officers told him he couldn’t have a dog on the beach.

Masters suffers from seizures, and Sheba is his service dog, but Masters said she wasn’t wearing her vest when the officers spotted them. Masters spent the night in jail and Sheba spent a night in an animal shelter. Masters’ sailboat had a leak and, in order to stay afloat, he had to scoop water out of it every 24 hours, according to USA Today. He couldn’t do this while in jail, so his boat sunk and he was stranded in Pensacola.

But he’s making the best of it now, and he said he always tries to stay positive.

“I was only worried about my dog,” he told USA Today of the arrest. “Everything else could be replaced. Nothing bad really happens. That’s what I believe. It’s just that not enough time has gone by to find out what the good (that) will come of the situation will be.”

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Now, Masters is selling his paintings for $25 to $45. People who read about his story have dropped off art supplies for him, and a nearby church offered him and Sheba a safe place to sleep at night, according to USA Today.

Last week, Daniel Dugan, organizer of the weekly Gulf Breeze Farmers Market, picked Masters up and drove to the Gulf Breeze Community Center, where a covered booth awaited the artist, so he could sell his paintings. Before the market began, though, Masters bough a new shirt and a pair of jeans. He has been wearing his previous clothes, which were splattered with paint, since his release from jail.

“Don’t I look fancy?” he asked USA Today with a smile. “I’m hoity-toity now.”

Masters is working on a floating tree series now, which shows that reality can shift and improve depending on your perspective, according to the Huffington Post.

“When you are down and feel in a rut just remember that it’s the nature of reality that all things change and that you can embrace it, like the tree,” Master said.

Masters had planned to travel to Key West, but he’s thinking of staying in Pensacola now. “I like it here, and the people have been really, really great,” he told USA Today. “They appreciate what I do, so why go somewhere else?”


Photos: USA Today/YouTube