Damari Philson’s paintings are fanned out on a table, vibrant with blues, reds, yellows and electric lines. He gathers one up in his hands: a portrait of a man with two faces, one sandwiched inside another.

The outer face is stoic — a deep blue, sullen expression. The inner one has a cartoonish, goofy smile.

“Someone may have a natural straight face, but on the inside they feel happy,” he explains. “They don’t necessarily show it. It’s more so like a mask that people put on showing that.”

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It’s interesting to think of what Philson’s opponents might make of that picture, and the artist, as they step into the boxing ring with him. As he advances toward them with raised fists, prepared to pummel, do they see something behind the gaze that glints with unfriendly intent?

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After a youth career that came with a few national rankings, Philson starts his pro career Saturday in the GTD Challenge against John Hale at 130 pounds, fighting on a card alongside some of his closest friends at Upton Boxing Center, the city’s hub of the sweet science.

The 18-year-old from Lanham contains multitudes: a painter and artist, a roller skater, a bowler, a recent graduate of Eleanor Roosevelt High School in Greenbelt. But every day Philson hops in his car, drives to Upton and puts on the mask.

“I’ve dedicated my whole life to boxing, and it’s a goal I want to achieve,” he says. “All the other stuff can wait.”

It’s agonizing, sweaty work. On a recent afternoon as he prepared for his pro debut, Philson donned a full-body sauna suit (it was already a 90-degree day) and shadowboxed. He put on his gloves and knocked around the heavy bag. Then he boxed up his things in a suitcase and drove nearly an hour home. The next day, he was coming back to do it again. And the day after that.

He’s been training in Upton for five years now. When he wasn’t old enough to drive, his dad brought him up after work. For the last year and change, he’s been training with the other pros at Upton, including Lorenzo “Truck” Simpson and Mia “Killer Bee” Ellis, taking advantage of a half-day senior year schedule to work on his boxing career. Even among the hardened vets, Philson’s dedication is noticed and lauded.

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“He don’t really miss days. He don’t cut corners. He don’t cheat,” Simpson says. “Sometimes he comes two times a day. It’s just amazing. He really wants it.”

It will be an important step in a pursuit that stretches back, if you can believe it, 14 years. Damari was 4 years old when his father got him into boxing, a passion Dion Philson never got a chance to pursue. Damari started competing when he was 8. As he got older, the Philsons looked for a gym that could bring him to the next level and settled on a long commute to train with Calvin Ford — whose best known student is Gervonta “Tank” Davis.

Damari Philson sits in the locker room at Upton Boxing Center waiting to spar on Aug. 2, 2023. (Dylan Thiessen/The Baltimore Banner)

There are wall-size murals and banners hanging of Davis, Simpson and Ellis in Upton; Philson dreams of being next. His best boxing attribute might be his footwork, and he has quick hands that are getting faster as he graduates to a higher level of training. Every weekend, Philson takes notes on boxing matches. In the recent title bout between Terence Crawford and Errol Spence, he took note of how Crawford dictated the distance and the tactics of the fight with his strong jab.

“The way he picked certain shots, he was patient, his defense was superb, his counters, his footwork also,” Philson says. “Watching boxing every weekend, I look at things like that.”

He’s helped finance his burgeoning boxing career with his artwork. As a middle schooler, Philson did a school project: a portrait in the style of Jean-Michel Basquiat, one of his biggest artistic influences. Encouragement from his parents and teachers to try his hand at art led to bigger works in high school, decorating canvasses at first to cover his bedroom, then later realizing he could sell the pieces.

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Philson’s works are those of an adolescent still finding his own voice. He’s done montages of cartoon villains, for example, but he also dabbles in the more abstract with spray paints and other street art materials, following his impulses. The colors he uses are always vivid — a departure from the kind of introvert that Philson can seem to others.

“Sometimes I’m just like, ‘Let’s see where my mind takes me, and go get a canvas and paint,” he said. “Whatever comes to mind, I just put it to canvas.”

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The art career, for now, is on hold, however. His website to sell prints under the moniker No Slihp (his last name spelled backward) is temporarily down, and he hasn’t made a new piece in months. He’s put down the paintbrush and closed his fists to chase his boxing career.

At his high school graduation, Philson crossed the stage and put up a few shadowboxing punches. His first pro fight will feel a bit like that moment, he imagines.

“My path is different from others,” he says. “You have people graduate, their next step is college. Well, I’m graduating from the amateurs in a way and going to the pros. So, yeah, I’m definitely looking forward to that, and stepping into a new life.”

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The goal? Become a world champion, obviously. It makes it easier to visualize because he fights in the same gym where Davis grew into one of the world’s best fighters, but the dream is his own.

It starts with Saturday. Philson said he wished “the week would just be over” so he could step in the ring. He’ll have Ford, Simpson and other fighters backing him, building his confidence. But, until you climb in, it’s hard to prepare for that moment.

“You can tell somebody, ‘Calm down, take it slow, just let it come,’” Simpson laughs. “But you’re gonna be so nervous. You just have to experience it.”

Damari Philson stands as his coach, Rodney Hunt, unties his gloves at Upton Boxing Center on Aug. 2, 2023. (Dylan Thiessen/The Baltimore Banner)


Kyle joined The Baltimore Banner in 2023 as a sports columnist. He previously covered the L.A. Lakers for The Orange County Register and myriad sports at The Salt Lake Tribune. He’s a Mt. Hebron High and University of Maryland alum. 

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