A collection of rare Keith Haring artworks, gifted to his childhood friend Kermit Oswald over nearly three decades, is coming to auction at Sotheby’s Breuer Building in May 2025. The trove includes a self-portrait from 1985 (estimated at $3–5 million), a painted crib and dresser ($250,000–350,000), a carved wood sculpture from 1983 (up to $800,000), and other early works on wood, fabric, and paper. These pieces trace Haring’s artistic evolution before his subway drawings and international fame, and were kept by Oswald, who was Haring’s best friend since kindergarten and later installed his shows.
The sale matters because it offers an intimate, personal view of Haring’s early practice and his deep bond with Oswald, revealing the artist’s experimentation across materials and his habit of creating gifts for loved ones. It also follows Sotheby’s successful 2023 sale of 31 Haring subway drawings for $9.2 million, underscoring sustained market demand for the artist’s work. The auction provides a rare opportunity for collectors to acquire pieces that have never before been on the market, directly from a lifelong confidant.