The Keith Haring Whisperer: Kermit Oswald in conversation with Jeffrey Deitch

Few figures hold such proximity to one of the most reproduced artists of his generation, Keith Haring, as does Kermit Oswald. Oswald and Haring were friends since childhood, before each went on to become celebrated artists in their own right. They also worked together: Oswald was famously the chief aesthetic collaborator on Haring’s radical carved wood sculptures, first unveiled at Tony Shafrazi’s 1983 landmark exhibition.

The origins of their friendship—and of a sustained intellectual and creative dialogue—may be traced to Kutztown, Pennsylvania, nearly two decades earlier, within the modest setting of a United Church of Christ congregation shared by their families. Oswald immediately recognized Haring upon his entrance into a kindergarten classroom, an encounter that marked the beginning of an enduring bond that would persist throughout Haring’s tragically abbreviated life. From whispered exchanges across church pews to the circulation of notes and drawings, their early rapport fostered the germination of a distinctive visual language—one that would come to underpin the formal and conceptual trajectory of Haring’s oeuvre.

Upcoming Auction

Contemporary Day Auction

15 May 2026 | 9:00 AM EDT | New York

In this context, Sotheby's is honored to present Haring’s House: Works from the Collection of Kermit Oswald, a rarefied assemblage of masterworks that offers both a privileged insight into Haring’s practice and a testament to the enduring influence of Oswald as both artist and advocate.

In April, the art dealer and curator Jeffry Deitch sat down with Oswald for a wide ranging chat on art, friendship and iconography. Read the their conversation below.

*Self-Portrait*, 1985. Estimate 3,000,000 - 5,000,000 USD .

Jeffrey Deitch: Kermit, you and I have known each other for a long time. We met in the early 80s when we were both part of this community. What I would like to ask you about is your childhood friendship with Keith going way back. What are things about your background and your relationship with Keith and his work that people don’t know about?”

Kermit Oswald: We were in the same church of course. We went to kindergarten together, but I have a visceral memory of him walking in the door to kindergarten and being one of the few individuals in our class who I recognized.

"It’s a language that was driven by an intention so powerful in him, that he almost couldn’t help himself."

JD: Keith seemed to have absorbed quite a bit from this religious background. You can see it in the work. You can see it in the images of rapture.

KO: I would agree with that sentiment. I think that one of the really important things about Keith’s work is that from a very young age, Keith had a very intense appetite for communication. And what I mean by that is that I believe it drove the iconography. I believe it animated so much of what he did. But for Keith, I think there was something inherent in his personality that he really wanted to get things across to people. The message on one hand is a really powerful part of it, however it’s also the methodology. The strength of the icons that he created is directly related to the strength of his conviction to communicate. That’s the interesting thing about his work. It’s a language that was driven by an intention so powerful in him, that he almost couldn’t help himself.

*Untitled (Painted Man)*, 1983. Estimate 40,000 - 60,000 USD .

*Untitled*, 1983. Estimate 200,000 - 300,000 USD .

JD: That’s one of the best explanations of what’s behind Keith’s work that I’ve ever heard.

KO: We were either juniors or seniors in high school, and the school owned three or four Ford Econoline vans they used to take kids to soccer matches. So Keith and I get the bright idea we’re going to paint one of these vans. So one night we go there at about midnight, we paint a van with red tempera paint, we use big mustard squeeze bottles that you can squirt the paint out. The next day, we got called into the principal’s office. We’ve got red paint all over our sneakers but we also have blue paint, and green paint, and yellow paint, and white paint. Cause let’s face it, all we do is paint. We didn’t get caught.

What I think we both learned by painting that van is that when you put yourself out into the public and when you try to do something with your ideas, with your skill, your material, whatever that thing may be, you have to be very careful, because it’s going to be understood as something subversive, that’s again rebellion of antagonistic to the status quo, right?

I know that he didn’t always understand exactly what he was gonna do, but it manifested itself.

JD: Keith must have derived a deep moral sense from his religious upbringing, because something that marks Keith’s work, as opposed to a lot of other artists of his generation, there is this moral message also there that’s the drive to do good through his art.

KO: He didn’t even know where some of this stuff was coming from. It would just come. And it seems like this is almost a cop out. You don’t really want to take responsibility for it. But the truth of the matter is it wasn’t all conscious, it just wasn’t. There were times when he stood up to that canvas, that piece of paper, that piece of plywood found on the street, and he just did something. And I know that he didn’t always understand exactly what he was gonna do, but it manifested itself. That’s the kind of intention to communicate. It was so boiling out of him that he couldn’t stop.

Left: *Untitled*, 1986. Estimate 250,000 - 350,000 USD . Right: *Untitled*, 1986. Estimate 250,000 - 350,000 USD .

JD: Kermit, you were instrumental in Keith’s work that you collaborated on sculpture, on wood reliefs. Tell us more about your artistic collaboration with Keith.

KO: It’s an interesting story because here you have two individuals who shared a common interest in a common love for making things. Keith in many ways, I always understood, got it very much from his father. His dad was super creative. We started drawing together when we were probably six or seven. Some of my earliest recollections I have about that, if it wasn’t on his back patio, it was on mine. It was what we did, when kids went out to play basketball or baseball, we sat around, got paper and made stuff.

Keith used a router to draw on all those totems. What’s beautiful about the router is that it’s not damaging the tool. It’s damaging the material you’re drawing on. So it takes the physical act, right, it takes the consistency in the uniformity of this beautiful line, which has become so much a part of how this man worked, right.

He drew on all those totems, all those all panels, everything that was in that show, all the small plaques, with one carbide tip. It never got dull. It never wore out from the beginning to end. It did the whole job.

JD: Your recounting about Keith’s approach to his work is so fascinating.

KO: I was in my Brooklyn loft, Keith would come out and see my wood pieces and be like “oh my god.” That’s when he finally said let’s make the totems. So that’s where that came from. And I was flattered. I thought it was super cool.