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Keith Haring's Early Works from Lifelong Friendship Head to Auction at Sotheby's

market-auction · 2026-04-24

A collection of rare Keith Haring works, gifted to his childhood friend Kermit Oswald, will be auctioned at Sotheby's Breuer Building in May 2025. The trove includes a self-portrait from 1985 (estimate $3M–$5M), a painted crib and dresser ($250K–$350K), a carved wood sculpture from 1983 (up to $800K), and a blue square drawing ($150K–$200K). These pieces trace Haring's early experimentation across wood, furniture, and screen-print. Oswald, Haring's best friend since kindergarten, received many works as personal gifts. The sale follows Sotheby's 2023 auction of 31 Haring subway drawings from Larry Warsh's collection, which fetched $9.2 million. A further 41 works from Oswald's collection will be offered in an online auction this October.

Key facts

  • Keith Haring's early works from his friendship with Kermit Oswald will be auctioned at Sotheby's Breuer Building in May 2025.
  • The collection includes a 1985 self-portrait of Haring as a sphinx, estimated at $3M–$5M.
  • A painted crib and dresser, made for Oswald's first child, are estimated at $250,000–$350,000.
  • A carved wood sculpture from 1983, part of Haring's Tony Shafrazi Gallery takeover, has an upper estimate of $800,000.
  • A blue square drawing from the same period is estimated at $150,000–$200,000.
  • Oswald and Haring were best friends since kindergarten; Oswald's father introduced Haring to woodworking.
  • Sotheby's previously sold 31 Haring subway drawings from Larry Warsh's collection for $9.2 million in 2023.
  • A follow-up online auction of 41 works from Oswald's collection will occur in October 2025.

Entities

Artists

  • Keith Haring
  • Kermit Oswald

Institutions

  • Sotheby's
  • Sotheby's Breuer Building
  • Tony Shafrazi Gallery
  • School of Visual Arts

Locations

  • New York
  • Kutztown
  • Pennsylvania
  • Upper East Side

Sources