Cups Coffeehouse


James Stewart is showing off his shoes, a pair of Reebok sneakers almost as new as the ink needled into his biceps. On his right arm is the number 9, and on the left the number 7, stitched together to signify the year the 17-year-old Digital Harbor High School student was born. Underneath the 9 is “Paula”—his mother’s name, and one made all the more important because she didn’t have to buy him his tattoos.

“I’m buying most of my stuff. I got nice sneakers on right now. I got a lot of nice stuff, so I’ve got to work to get nice stuff,” he says. “I can’t keep going to my mother.”

Using his own money is a point of pride for Stewart, who, on this particular Friday afternoon, is wearing only one article of clothing he didn’t have to buy: his CUPs Coffeehouse shirt. It’s Stewart’s first job, and while barista isn’t a position he intends to carry long-term, working at this small, corner coffee shop in Baltimore’s Hollins Market neighborhood has not only made his wallet a bit fatter; it also has helped him grow up in and out of school, he says.

“I never had any work experience. Working, believe it or not, it gets you mature,” says Stewart. “Now in school I don’t get in trouble. I come to the school with a whole different demeanor. I come to school ready to work.”

The shop itself is owned and operated by Holly Gray, an ebullient woman in her late 30s who moved to Hollins Market about 12 years ago and founded CUPs two years back.

“I was constantly frustrated by the fact that there was nowhere for me to go if I wanted to grab a cup of coffee or just meet with a group of friends,” she says.

But the coffeehouse serves a secondary, more significant purpose. A nonprofit coffee shop, CUPs is an extension of the volunteer work Gray did tutoring teen-age girls through an after-school program at Monroe Street United Methodist Church. During that time, she would eventually open her house and invite the girls to work on homework there.

At CUPs, a similar vibe pervades, as children and teens from the neighborhood travel in and out to purchase lunch or a drink, spend time drawing or grab a book from the shop’s library and read.  The most intriguing action is happening behind the counter.

Gray exclusively hires teens and adults between 16 and 24 who are transitioning out of foster home care or considered at-risk—potential victims to the perils of street violence and drug-dealing. Her employees, seven baristas right now, take life-skills classes twice a month in financial literacy, resume writing and more. They also complete eight hours of community service in the Hollins Market neighborhood every month. Stewart, who started working at CUPs in August 2013, spends his time in a neighborhood rain garden steps away from the shop on South Arlington Avenue.

“They all really struggle with confidence, with the ability to speak to people that are unfamiliar,” Gray says of the kids she has hired. During CUPs’ first year of operation, she says all 12 of her employees had been physically attacked, at home, in the neighborhood or at school. “They carry around these things. Inwardly they feel beat down.”

So far Gray hasn’t drawn a salary from CUPs—all the money the shop makes goes toward paying her employees—and keeping the lights on and the Zeke’s Coffee brewing. The ultimate goal is to have her employees spend a year at CUPs, and then find full-time employment elsewhere or pursue their education.

“I had my first job when I was 14,” says Gray. “I had all those opportunities and I could develop and follow that path to success, and those just weren’t readily available here.”

Stewart knows his time at the shop is almost up, but he’s ready for the next step. The eldest of three, he’s been the man of the house for 11 years, looking out for his mother and younger sisters. He sets aside a portion of his wages for his family. After graduating high school, he plans to head to community college and begin studying to become a registered nurse. The future’s uncertain, but the sandwich wraps he’s made and the cups of coffee he’s poured have done more than give him some pocket money.

“You can grow up in a community like this and still make it somewhere—that’s what Miss Holly does,” he says. “She’ll give you a chance.” 

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