Last July, just before the Republican Party National Convention, Jeff Zimmermann was painting a mural, titled The Party, outside his studio, on the corner of California and Cortez. An African-American man was walking by and stopped to study an image that was already finished. "He asked, 'Is this a noose?'" Zimmermann recalls. "I probably said something like, 'Yeah, maybe.' That was the whole interaction." The man moved on.

Minutes later, two plainclothes policemen in an unmarked car arrived and questioned Zimmermann. They told him they'd gotten a call about a hate symbol. "They asked, 'Is this some kind of message, is there some kind of meaning here?'" Zimmermann says. Though he prefers to leave his murals open to interpretation, he told the cops it's obviously an upside-down noose, and no one was in it (except for an image of a resilient Wile E. Coyote, representing "people's cartoony idea of immigrants," as Zimmermann would later tell me.) He'd painted ropes and knots and chains in other areas of the wall, so maybe this was a lasso, or a comment on capital punishment, he said. Satisfied he wasn't some kind of neo-Nazi vandal, the police moved on.

Zimmermann, who's white, is no stranger to provoking racial misunderstanding in his work. He's known for his large-scale murals in Pilsen and other neighborhoods and cities featuring portraits, obscure symbolism, and visual puns. In 2009 he was painting A Note for Hope, a monumental mural in downtown Memphis on the theme of interracial unity, when his image of an elderly black woman with a gold front tooth prompted an outcry from members of the local chapter of National Action Network, Reverend Al Sharpton's organization. They thought it was "an offensive stereotype," according to a New York Times article. In fact, it was a real-life portrait of a longtime Memphis resident, 80-year-old Savannah Simmons, whom Zimmermann had photographed. The former factory worker attended the dedication and loved her picture; critics backed down.

"I try not to do propaganda or political art, but I'd like to be a political artist," Zimmermann says. He's a 46-year-old native of Westchester, Illinois, who graduated from UIUC with a graphic arts degree. Zimmermann then spent two years with the Jesuit Volunteer Corps in a shantytown in Tacna, Peru, as a social worker for street kids. Returning to the U.S., he took film classes at Columbia College and, as a youth worker, did his first mural, in Pilsen, in 1996. "I try to leave things open using poetic and abstract thinking," he says. "I'm more like, 'Let's talk about it' rather than 'Here's the solution.'"

If you live in Chicago, you've likely seen Zimmermann's acrylic-paint murals: around 19th and Ashland (where one of his best-known pieces, the tripartite Familiar, was recently whitewashed), along Lake Shore Drive at 47th Street, in the Oak Street Beach pedestrian tunnel, or outside the Morse el station. The works mainly fall into two categories. There are corporate or nonprofit commissions, like the prominent Conagra Mural (Urbs in Horto), which includes references to the title Chicago-based food giant's products and was dedicated in October at the Bloomingdale Trail entrance near Leavitt and Milwaukee. Then there are the more personal statements, such as Chainge, a 1998 wall at Chicago and Milwaukee that shows a blind musician and a message in braille (using glued-on pennies). (Paid Programming, a 1997 piece in Wicker Park about gentrification, was eventually demolished to make way for condos.) With the noncommissioned work, Zimmermann asks building owners for permission to paint what he pleases, pro bono, though he says he won't do anything in public "too supercharged, like paint a gun." (He has included gun images in several museum mural installations, including Dark Matter, which was at the Museum of Contemporary Art in 2003.)

While Zimmermann's big commissioned walls have fairly straightforward imagery, the personal ones largely don't: you have to stand there for a while and puzzle them out. They're often deliberately ambiguous, which can complicate the message. (You'd likely never know, for instance, that his images of vanilla ice cream indicate white privilege.)

The 120-foot-long The Party belongs in the "personal" group—the landlord of Zimmermann's Humboldt Park studio building was supportive of it. Created during the divisive summer campaign season in the run-up to the conventions, The Party was meant as an indictment of the Republicans' racist, hate-mongering agenda. But, as Zimmermann cautioned, "both the left and right parties are over and now what are we left with?" Donald Trump, for one. Now that he and his cohorts will soon occupy the White House, the mural's implication of a "hanging party" has taken on new urgency.

Along with images of revelry—crumpled-up red and blue cups, red and blue pills, empty shot glasses, hot dogs, candy—the wall also includes allusions to the new regime's gilded capitalism and its threats to immigrants, environmentalists, racial minorities, and women's and LGBTQ rights. Suggestive gang symbols (top hat and cane) near another noose might be commentary on youth violence, or on the political gang in power assaulting democratic institutions. Viewers may not get any of this, and to Zimmermann, that's fine—you can make any kind of associations you want. "Maybe it's better that people never figure it out," he says. "It's better if you're never sure. If it's propaganda—you get it, you understand it, then you don't need to look at it anymore. I hope to get people talking. I don't want to give people the answer." Still, later, he e-mailed, "It's finally a time when politics can again be involved in the art world."

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