It’s just past 3 p.m. on a scorching July afternoon, and Jake Troyli watches as a group of elementary school children file into a studio space in a South Chicago community center. Standing at a formidable 6 ’10”, Troyli towers no less than two feet over most in the room at the SkyArt Center, but the additional inches don’t seem to keep his jitters at bay.
“I’m kind of nervous,” laughs Troyli. “I present to adults all the time, but it’s kind of intimidating to talk to kids.”
The 33-year-old painter spent the morning bouncing around the center asking kids about their ambitions and dreams and hyping them about the boundless futures that lay ahead of them. But Troyli, who moved to Chicago from Florida in 2020, isn’t only here to commune with aspiring artists. He also hopes to translate his conversations into an idea for a 30-foot tall mural. The piece was commissioned by SkyArt, an arts nonprofit that runs free kids programs for its second location in Garfield Park. The center will anchor a new neighborhood arts corridor in a block that has been historically violent.
The project is part of Next Stop: Chicago, a series of six public art installations and events funded by Gertie, the cultural consultancy group founded by Abby Pucker, daughter of Gigi Pritzker and a cousin of Illinois Gov. J.B. Pritzker. Gertie raised more than $400,000 to spotlight artists and arts organizations working in historically underdeveloped neighborhoods along the CTA Green Line train. Next Stop: Chicago will launch during the Democratic National Convention and will be one of many art happenings, some coordinated and others not, to capitalize on the city’s moment on the international stage. Troyli, for his part, is one of the more commercially successful among the group and brings a certain buzz factor to the operation.
“Jake’s work has this playful quality,” says Devon VanHouten-Maldonado, the executive director of SkyArt. “Even when he’s wrestling with deep issues around race or incarceration or economic divides, he does it with a sense of play. He wants art to be accessible and that lends itself really well to this particular project.”
The mural project marks the start of a particularly busy season for Troyli, who has fast become one of the city’s most exciting emerging art stars. His paintings, which marry a unique blend of Renaissance symbolism with playful, exaggerated comic book colors and figures, are coveted by private collectors and museums alike. In August, Troyli’s work will be featured in a show at Galerie Droste in Düsseldorf, Germany.
Two months after that, one of his paintings will hang as part of the group exhibit “Get in the Game’’ at the San Francisco Museum of Modern Art. And in November, Troyli will open his third solo show at Monique Meloche Gallery in Chicago. (Troyli sold every single painting at his two previous solo exhibitions.)
“Jake is not painting like anyone else out there,” says Monique Meloche, founder of the eponymous Chicago gallery, which started representing Troyli in 2019. “There’s just so much depth behind the surface of what he presents.”
Those layers, says Troyli, reflect his own melange of early influences. Growing up as an only child of a single mother in Saint Petersburg, Florida, Troyli found comfort and company in comics like Calvin and Hobbes, The Far Side, and later works by R. Crumb. Perhaps most influential, says Troyli, was his subscription to Mad Magazine. “There were these technically brilliant artists that also had something to say and it was accessible,” recalls Troyli. “I didn’t have to go to the Whitney Biennial, I could just pick it up and read it.”
His mother’s job at a local theater company in Saint Petersburg also piqued Troyli’s interest in imaginary worlds. “I liked this idea of [amateur] set design and what it takes to make something believable,” says Troyli. “How the line is blurred between performance and self has always been interesting to me.”
That dynamic carried new meaning when Troyli’s basketball career took off. (Troyli was six feet tall by the eighth grade.) After getting recruited to play at Presbyterian College in South Carolina, Troyli began to consider the ways in which he himself felt pressure to perform as a Division 1 athlete. That dual-edged celebration and exploitation of Black bodies would later become a central theme in Troyli, the artist’s, work.
Consider “Out to Dry,” a 2022 painting that depicts an elongated Black man draped over a telephone line wearing nothing but white socks and a single slide sandal. The man, like many of Troyli’s figures, stands as an avatar for the artist. In the image, the man looks directly forward as though to confront the viewer; he has not resigned to his contorted position. Troyli’s 2023 painting “Training” centers the same figure, but this time he wears a thick protection suit, his eyes resigned and cast down as a quartet of dogs bite at his limbs.
Troyli’s potent, pointed images, however, were not what the Florida native first put on canvas. “After college, I spent a while making awful paintings,” laughs Troyli. “They were like these were Norman Rockwell ripoffs.” Nonetheless, the work was good enough to land Troyli a spot in a Master of Fine Arts program at University of South Florida in 2016. But, says Troyli, “I got eviscerated in the [school art critiques] at the end of my first semester.”
To help Troyli find his voice, his instructors urged him to visit the Kerry James Marshall retrospective “Mastry” at the Metropolitan Museum of Art in New York City. Marshall, a Chicago artist and MacArthur “genius,” has earned a place among America’s canonical painters thanks to his prodigious depictions of Black life in America. “I walked into that show not understanding that contemporary art had real power and then I saw those works and was actually struck,” recalls Troyli. “It changed my life.”
It changed his work, too. Over the next three years, Troyli sharpened his craft and his social criticisms. He built motifs — sports narratives, the commodification of Black bodies, the elasticity of identity — and explored them through the comic styles he loved. Troyli also played with color and scale. Afros, for example, feature prominently in Troyli’s works and often take on an almost architectural quality. By the time Monique Meloche first discovered Troyli’s work in 2019, she knew she’d found something special.
A week after visiting SkyArt, Troyli is back in New Jersey where he has a residency through 2025. This one comes after a yearlong stint at the prestigious Academie des Beaux-Arts in Paris, France. Troyli insists, however, that Chicago remains his homebase.
He’s spent the last week considering the mural. What started as haphazard doodles on his iPhone was later refined to a bold, graphic image of a young man climbing a ladder while painting clouds against a cobalt blue sky. The character sports a signature Troyli afro and red and white Chicago Jordan sneakers. “I wanted the figure to be upwardly mobile and ascending,” reflects Troyli. “I also wanted the image to be super graphic and big. Like you’ve encountered a giant.”
“In a really divisive moment, when a lot of attention is on Chicago, this mural offers an opportunity to highlight how we care for each other,” said VanHouten-Maldonado, the SkyArt executive director. “So often we miss all of the riches that exist in these neighborhoods, and I think it’s important for us to lift up voices in the communities and counter that narrative.”
With Troyli largely away, a team of professional muralists will complete the project by the mid-August DNC, and SkyArt plans to introduce the work during a community event on Aug. 21. And when they do, Troyli hopes to encourage viewers, and especially the SkyArt kids he met, to forge their own ladders. “I want to show that you have agency in building the world you want to be a part of,” says the artist. “You can create your own possibilities.”
Elly Fishman is a freelance writer and the author of Refugee High: Coming of Age in America.
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