In June 2023, Ricardo Gamboa interviewed Sean Tyler and Reginald Henderson, two brothers who were tortured into confessions by the Chicago Police Department in 1994. The conversation was part of a collaboration between Gamboa’s news talk show The Hoodoisie and the Chicago Torture Justice Center. During the interview, Gamboa could not stop thinking about The Pillowman, a play about two brothers, Katurian and Michal, who undergo investigation for a series of child murders that bear a striking resemblance to fictional stories written by Katurian.
Gamboa saw an opportunity to produce a version of The Pillowman for local audiences, drawing parallels between that story and Chicago’s own history of police torture. Gamboa’s Concrete Content is bringing The Pillowman to Humboldt Park’s AfriCaribe Cultural Center. As with many of the theater company’s past productions, the cultural fabric of Chicago is woven seamlessly into the show’s set design, cast, and crew.
Omari Ferrell and Tyran Freeman, longtime friends and south side Chicago natives, play Katurian and Michal, respectively. The cast also includes Sean Parris and Roy Gonzalez, along with puppeteering by Opera-Matic co-directors Agnotti Cowie and Rocio “Chio” Cabrera. Chicago spoke with Gamboa and the cast on how their approach to the production is rooted in the history and social issues of Chicago, themes and messages they hope to convey, and their effort to shake up the traditional theater model. The play opens today and runs Fridays and Saturdays through April 12.
You’ve had the idea to produce The Pillowman since 2023, why wait until now?
Gamboa: I was involved in other things — organizing in support of Palestine, continuing my other organizing commitments here in Chicago, and really didn’t think I could mentally jump into this. I also found Ruth on the Rocks. But this play only became more relevant. We were watching protestors being brutalized and the media operating as propaganda. It just felt like this was a play that needed to happen right now when these conversations are happening. The most important is the fact that 2025 is the [10th] anniversary of the [Chicago] Reparations Ordinance. I was like, “Yo, we need to put this up.”
What was it about The Pillowman that made you say, “This is the perfect medium for me to speak on these issues?”
Gamboa: We’ve had this blossoming of social movements that have happened around immigration, around anti-Black police violence, and the work has often come off as very didactic. One of the things that I like about this play is that it isn’t easy. This play forces the audience to really think through their borders of compassion. Situating [the play] within Chicago to mark the history of police torture, the Reparations Ordinance, this moment where we are living through the rise of U.S. fascism and political repression, and where there’s a genocide going on, I hope it forces people to think and navigate through these things.
How did you go about asking the audience to consider these issues?
Gamboa: It’s taking this kind of western classic — modern classic — and forcing it to deal with what often the theater doesn’t, forcing it to deal with the realities that are obscured and repressed. For me, putting on this play, taking this play and actually recontextualizing it in somewhere like Chicago with Black protagonists, with young protagonists, kind of takes that writing and exposes that reality of, again, what western theater is. It kind of shows some of the preconditions and what’s at the root of that stuff. I think it creates an interesting conversation both about the practice and industry of theater [in Chicago].
How did you ensure Chicago was properly represented?
Gamboa: The way everything was sourced. One of the things I thought about is Chicago and concrete, so it’s reflected on the set. The set was designed by me and built by EG Canzano. It’s a collaboration with various Chicago artists, like Chris Silva and Roman Caballero, both local, Latino graffiti artists. The wording of graffiti you see on the pillars as soon as you walk in was pulled from various Chicago protests, posters, and other graffiti we saw in the city — just even going around and working with community connections and Mexican American collectors that hooked it up.
The costuming is also very much giving Chicago.
Gamboa: You cast your play but you also cast your audience. You say, “I’m not putting on this play for white people at Steppenwolf. I’m putting on this play for communities of color, for working class people. For people that are living right now.” That immediacy changes how things look. The Broadway version, since Katurian is a writer, they have him in a sweater vest, (laughs) here they got airbrush on, silkscreen shirts, their hoodies — stuff like that.
What made you choose the AfriCaribe Cultural Center as the location for the play?
Gamboa: Well, Humboldt Park has a huge history of resistance. [AfriCaribe] is a mile away from Homan Square, which was a CPD black site. In 2015, The Guardian had an article that exposed it (the site) for the torture that [CPD detective and commander] Jon Burge and other people have been doing for decades.
Can you tell me a bit more about this space and its significance?
Gamboa: This is run by Evaristo “Tito” Rodriguez. He founded this to bring attention to the African roots of the Caribbean, principally Latin American-Caribbean. It’s kinda a fugitive space: He doesn’t take funding from nonprofits, so it’s kind of autonomous. I thought this would be an awesome space and a meaningful space to put this show on. So it’s kind of thinking through Chicago, but also how Chicago itself is a convergence of time and space and that the oppressions that we endure in Chicago are part of bigger histories and maps across time and space. That’s kinda where the set comes from.
What do all of you hope audience take from this play?
Gonzalez: I hope they enjoy the show and if they yield anything out of it that is socially minded or socially conscious, that’s cool. I just hope they think it’s good. I never do this to change anyone’s mind or persuade anyone of anything ever. And I’m also not looking to inflate my own ego and be like, boy, wasn’t I good? I hope you think the whole thing is good
Ferrell: No, I need people to know, damn, he was great. (laughs) No, I guess for me, I want somebody to walk away contemplating something. There’s a whole lot of emotional nuance and levels in this show. I want people to question what they do and why they do it. Katurian writes all these fucked up stories and he writes them, I believe, with the purpose of being true to the world that he’s living in. But I wonder what good he does and what good is some of the art that we participate in or look at or idolize?
Freeman: To me, this play is a pointer. I think if people are here and they’re paying attention to it, they will pick up on a lot of those things that this story is pointing to. So I think it’s good that people come see it for that reason.
Parris: I want to be successful. I want it to be sold out. I want it to be in consideration of extending — because it’s that good. And I hope people in the neighborhood come out. Ricky puts theater up at places that they don’t often get theater and it becomes an afterthought. This kind of thing matters.
Gonzalez: Ricky and his commitment to this production, I do mean this sincerely, is so emblematic of the Chicago theater experience. This is the most intimate setting I’ve ever been a part of. And I’ve done a lot of shows in this town. This is a reminder of what Chicago theater can and does stand for and — not to be too romantic about it — it’s kind of like a punk show where there’s no barricade, no bouncers, there’s no real separation between the artist and audience here. As an actor, I love that shit, dude.
Gamboa: I do think when Roy’s talking about Chicago theater, it’s also about trying to paint a different vision of it. A Chicago theater that responds to the moment.