Kermit Oswald’s Keith Haring works
This May, Sotheby’s will also offer a deeply personal group of works by Keith Haring from the collection of his lifelong friend Kermit Oswald, bringing to market a trove that has remained largely unseen for decades and offers an intimate lens into the artist’s practice between 1977 and 1989. Best friends since childhood and an artist himself, Oswald and Haring were united by a shared love of art from an early age, drawing together from around age six or seven, delivering their paper routes as kids and, as teenagers, catching a $10 bus to Manhattan to spend entire days visiting museums before returning home to paint late into the night. Throughout their adult lives, they continued exchanging letters between Pennsylvania and New York, sharing ideas and working together.
The trove is anchored by the exceptionally rare Self-Portrait (1985), acrylic on canvas, one of just six known examples the artist ever produced, offered with a $3-5 million estimate and included in recent surveys at Palazzo Civiltà del Lavoro and Galerie Nadeau in Philadelphia, both in 1990, and a show at Fondazione La Triennale di Milano in 2006. Other highlights include a carved wood Untitled (1983), estimated at $600,000-800,000, from the pivotal body of work first shown at Tony Shafrazi Gallery, as well as The Blueprint Drawings (1990), a complete set of 17 screenprints created in the final months of the artist’s life, estimated at $300,000-500,000. Equally emblematic of Haring’s personal iconography applied across objects are a hand-painted crib and dresser—each estimated at $250,000-350,000—created as a gift for Oswald’s first child and bearing the artist’s signature imagery, alongside additional works on paper such as Untitled (1980s), estimated at $150,000-200,000, reflecting his engagement with media, language and urban visual culture. The auction coincides with major surveys of Haring’s work, including Keith Haring at the Brant Foundation, New York; Keith Haring: In The Street at Free Parking, New York; and the upcoming Keith Haring in 3D at the Crystal Bridges Museum of American Art in Bentonville, Arkansas. An additional selection of 41 works—on paper, collages, sculptures and ephemera —also from the Oswald collection will be offered in a dedicated online auction in October.


