Scott Benner of ArtLifting. Photo credit: ArtLifting

At first, the elegant art shows in downtown Boston were uncomfortable for Scott.

Groups of people entered wearing peacoats, while servers in black poured complementary wine. Pretty people had pleasant conversations about the paintings on the walls. Next to the fruit platter sit a spread of choices — salami, pepperoni, or prosciutto? Gouda, Brie, or Tomme De Chevre?

Scott didn’t have many choices at Father Bill’s shelter in Quincy. He had to be in the shelter by 6 p.m., out by 7 a.m. He ate mac and cheese, canned peas, and milk for dinner. People shook and sweat from drug withdrawals, while others scoured for their next hit. There were fights over the bathroom, fights over food, fights over other fights.

Scott’s artwork brought him to the edge of two different worlds: one with art shows on Newbury Street, and the other with food stamps. Teetering between them was strange, hard to navigate.

But on this chilly December night inside the Boston Convention Center, Scott seems comfortable. He weaves through the crowd, stopping frequently to shake a hand or catch up with a familiar face. These art shows are now routine, and so is his outfit: a faded black t-shirt, light washed jeans, and scuffed brown sneakers. He refuses to wear a suit — it’s just not him.

“Are you the artist?” a lawyer wearing a blazer and a buttoned-up shirt asks.

“Ha!” Scott exclaims, his face blushes. “I guess I am! I’m the artist named Scotty.”

Winfield “Scott” Benner always knew he had talent, that much was obvious. But he never thought his artwork could help him escape the spell of alcoholism, anger, and bad luck that had come to rule his life.

He once had a job he liked and a home with Julie, a woman he loved. But then a “perfect storm” hit. He was laid off from his job with American Steel, left to piece together a string of odd jobs in construction and shipping. Eventually, the constant unemployment left him prone to outbursts of rage, drinking, and frustration. He would still draw from time to time, but a rare disease called Horner’s Syndrome cursed him with debilitating headaches. It was hard to concentrate for long periods of time. The money was running out. Julie got cancer.

His life became an “accident happening in slow motion,” which crescendoed into splitting up with Julie and selling their house in 2013. He traveled between Rhode Island and Maine for a few months, eventually settling in a woody area outside of the Quincy Center station — where, if he wrapped himself tight enough in the tarp he bought from the dollar store, the insects wouldn’t bother him.

It took him a few months to learn how to be homeless, but some of the rules were simple: don’t make a lot of noise, don’t make a mess, and if the cops come, get the hell out.

There were a lot of minutes to fill. On cold days when he grew tired of drawing, he would pay $2.50 to ride the Red Line train back and forth from Quincy Center to Alewife. It was monotonous, but at least it was warm.

And so he went: Quincy Center, Wollaston, North Quincy. Thirteen stops later, Alewife.

And then back.

Alewife, Davis, Porter, Harvard, and so on.

He’d sit there, his day trudging along the Red Line, just “waiting.” But waiting for what, exactly, he did not know.

Amid the tumult a year later, came what he calls his “light at the end of the tunnel”: ArtLifting.

After nine years of working with art groups in shelters, Liz Powers started ArtLifting with her brother in 2013 to help people with similar narratives to Scott: homeless, disabled, or disadvantaged with under recognized artistic talent. She wanted to help them earn something.

“I thought, you know, I’m seeing all of this amazing artwork in these shelter groups, but what about the rest of the world? What about all the people who would want to buy the work if they even knew it existed,” she said.

After exchanging a couple of emails, Liz and Scott first met in 2014 outside Harvard Yard. Scott, with a big white beard, carried a tattered leather portfolio filled with his artwork dating back to 1971. Liz said his artwork was unique, and knew immediately that ArtLifting could help him.

Photo credit: ArtLifting

Many of Scott’s pieces are created on pads of paper, and comprised of lines from 0.2 mm fiber tip pens. Individually, the lines are shaky and faint. But, stroke by stroke, they become so much more — intricate flowers, abstract geometric patterns. The images do not have any color, but they have movement and texture. Nearly all of his pieces are nameless. He says there isn’t any “deeper meaning” to his drawings, but people still prod him for an answer.

“People like to tell me random things they see in my drawings — it’s like a Rorschach test,” he said.

ArtLifting began in Boston and runs as an online marketplace. It has expanded to eight cities and helps sell the work of 60 artists. The company’s customer base ranges from everyday customers to corporations like Staples and Microsoft. For each sale, 55 percent of the profit goes to the artist, and the rest is recycled back into the company to help it grow its reach as a public benefit corporation.

Scott didn’t think ArtLifting would help him make more than a few sales here and there. He knew his art was good, but not that good where anyone aside from friends and family would pay for it. Drawing provided him with what he lacked on the streets: a sense of ownership, pride, and escape. At the time, those feelings sufficed.

But then his first piece sold through ArtLifting for $350. The next went for $500 and another for $1,700. The downward trajectory of his life started to curve upward. Seven months later, he left the streets of Quincy and moved into a one bedroom in Old Orchard Beach, Maine.

This, he began to remember, is what it felt like to have money: a guaranteed bed each night, a dinner made of more than just peanut butter and jelly, clean clothes. Hope.

“There are two types of homeless people: there’s chronic and there’s transient. I always considered myself transient. I went through it. I had a life and I lost it, but I found a way out of it,” Scott said. “This is a vast improvement from where I’ve been … but my ordeal is not completely over. But at least I have it within grasp.”

Hope, according to Scott, is what separates the chronic homeless from the transient.

At the Quincy Library on a balmy December afternoon, Scott recognizes a lot familiar faces. It has been a year since he has been back to this library — the old spot where he and dozens of other homeless people would spend their days — and not much has changed there.

“Homeless and libraries kind of go together,” Scott said. “They have bathrooms, water, Wi-Fi, and computers. You can do things there.”

Several 40-somethings and 50-somethings sit inside the library lobby, some charging their electronics and others sipping water. One man perched in a corner leans against a trash bag swollen with stuff. A woman dressed in ragged clothes bursts through the front doors of the library and begins telling a story to another man. She smells of alcohol and her voice echoes through the room.

Scott, with his white hair, round face, and half-buttoned flannel shirt, walks outside the library and toward a group of people smoking cigarettes on the sidewalk. One by one, they slowly turn around.

“Scotty?” a man in a wheelchair rolls over to get a better look.

“How you doing Eric?” Scott and him grab hands, and Eric raises himself up from his chair and pats him on the back.

Scott didn’t need to bring up ArtLifting, Eric already knew. Eric reaches down into a pouch behind his wheelchair and pulls a small tattered sketchpad out of a dirty plastic bag.

“What do you think of these?” Eric asks, his worn hands flipping through sketches of graffiti patterns and caricatures of people he and Scott both knew from the streets.

“I’ve always told you your stuff was good,” Scott says.

“I don’t think people will buy this shit like they’ve bought yours,” Eric says. He closes his notebook and places it back into its plastic bag.

“It’s worth a shot, man,” Scott said. “Don’t lose hope … you never know.”

Check out Scott’s artwork here:

Follow me on Twitter: @TrishaThadani /

City Hall @sfchronicle, focusing on the Board of Supervisors. Used to write about visas and startups. One of those East Coast transplants, by way of Boston.

City Hall @sfchronicle, focusing on the Board of Supervisors. Used to write about visas and startups. One of those East Coast transplants, by way of Boston.