Our five-week series comes to a close with P·P·O·W. Co-founders Wendy Olsoff and Penny Pilkington reflect on the gallery’s decades-long dedication to socially engaged art—sustaining long-term relationships with artists, bridging generations, and fostering meaningful engagement with pressing cultural and social issues.
PLUS MAGAZINE: Can you share the story of how you first decided to start a gallery together, and what do you remember most about each other from those early days? Also, what ultimately drew you to Tribeca?
WENDY OLSOFF: Penny and I opened our gallery in 1983 in the East Village. We started it because the existing galleries weren’t showing work that felt relevant to our political moment. The East Village was very inexpensive at the time, it was a neighborhood of immigrants and artists, and also the center of the drug trade. Despite that, a vibrant gallery scene emerged, complete with clubs and restaurants that catered to the neighborhood.
What do I remember about Penny? She came from London, and her parents had a gallery. I was in awe of how she could navigate a night at Danceteria or an opening at MoMA with equal ease.
Over the years, we’ve had eight spaces, including our original one in the East Village. What drew us to Tribeca in 2019 was the opportunity to have a ground-floor space again, in an accessible neighborhood frequented by a cross-section of New Yorkers. The other galleries in the neighborhood were colleagues we admired.
PENNY PILKINGTON: Wendy and I met on my first day of work in New York, at a gallery on the Upper East Side. While we came from very different backgrounds—Wendy, a New York native, and I from London–we became fast friends and then roommates. It quickly became clear that our shared passion for art and strong work ethic made us a great team. We brought very different skills to the table, and after working for other galleries for a few years, we decided to go out on our own. We moved into our first space in the East Village with no artists, no strategy—just our guts.
P: How have you seen the Tribeca community evolve over the years, both culturally and artistically?
WO: Tribeca has evolved, but not as dramatically as neighborhoods like SoHo or Chelsea. While more galleries have opened, the neighborhood itself has retained its character. There hasn’t been the usual influx of luxury retail or trend-driven restaurants that often signals dramatic change.
We’re located at the northeastern edge of Tribeca, right by the courts, City Hall, and a major detention complex—a crossroads of government, legal, and commercial life. Just steps away are the retail bustle of SoHo and the street vendors of Canal Street. That mix has stayed consistent. What’s changed is the artistic landscape: galleries have moved in, drawn by the neighborhood’s affordability, high ceilings, and accessibility—all of which support more ambitious exhibitions and deeper engagement.
P: Where are your go-to spots in the neighborhood?
WO: We tend to stick to our favorites. One of the things we looked forward to when moving from Chelsea was having more lunch options, but in the end, our routine hasn’t changed all that much. You’ll usually find us at Frenchette or The Odeon, reliable spots that are now part of our daily rhythm.
P: In an art world driven by “the new,” how do you approach archiving, contextualizing, and ensuring their continued relevance?
PP: We’re formal custodians of the legacies of artists we worked with during their lifetimes or who were part of the downtown community of the 1980s—artists who were not only peers, but friends. Our commitment to preserving and championing their work is central to the gallery’s mission.
While the art world is often driven by a hunger for “the new,” there’s also a growing recognition of the value in revisiting and recontextualizing historical voices—especially those previously overlooked. These artists provide cultural memory and critical depth. For galleries, collectors, and institutions, they anchor programs with historical perspective and integrity.
P: How have your curatorial strategies or day‑to‑day management evolved with Eden’s influence? Are there particular exhibitions or initiatives in the Tribeca space that embody an intergenerational dialogue between P·P·O·W’s activist roots and contemporary perspectives?
WO: We’re incredibly lucky to have Eden [Deering] as part of the gallery, as she grew up with our program and deeply understands its values. She has curated five dynamic group exhibitions that build on the history of P·P·O·W while expanding it in meaningful ways. Eden is committed to honoring the legacy of the estates we steward while forging relationships with a new generation of artists—many of whom Penny and I may not have encountered on our own.
For example, Eden has brought Kyle Dunn, Grace Carney, and Harry Gould Harvey IV into the program. While showing young artists is nothing new for us, Eden carries this forward with a clarity of vision and integrity that ensures continuity across generations. She also works closely with artists like Judith Linhares, Gerald Lovell, Elizabeth Glaessner, and Erin M. Riley—artists who embody both our activist roots and a contemporary lens.
We’re also fortunate to have a passionate and driven team of young directors who bring fresh perspectives to every facet of the gallery. We’ve always believed that galleries must evolve—or risk becoming trapped in their own era. That was never the kind of space we wanted to be.
P: As a gallery that has always prioritized artists, how are you navigating today’s market dynamics? What shifts are you observing that excite or concern you most, and how do you continue to protect depth and longevity in a market that often favors immediacy?
WO: We’re in the midst of a complex moment, facing multiple challenges in the art world. One thing we’re deeply grateful for is that we never expanded to multiple national or international locations. This decision allows us to remain agile, manage costs carefully, stay grounded in our vision, and support artists in the way we know best—by giving them time and space to create.
Right now, there’s so much noise and pressure that it’s easy to forget the value of slowing down, not saying yes to everything, and not chasing immediacy. Our focus has always been on building long-term careers for artists and ensuring the gallery’s longevity. It’s not easy, but we know it’s possible, and it’s the most rewarding part of our work.
PP: Exactly. Recognition doesn’t always happen overnight. Often, it starts with a small circle of writers, curators, and fellow artists. You have to trust the process—and have patience as collectors catch up. We’ve always believed in showing work we stand behind, not just what’s market-friendly. Yes, some collectors favor immediacy—but many are hungry for deeper, more complex conversations.
That said, costs across the board are too high right now, and everyone—galleries, institutions, collectors—needs to take a step back and remember why they entered this field to begin with.
For us, it’s always been about the artists. That hasn’t changed.