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The 20 Most Expensive Artworks Hitting the Auction Block This Season

The May 2026 New York auctions at Christie’s, Sotheby’s, and Phillips will feature 20 high-value lots priced at $30 million or more, including works by Andy Warhol, Jasper Johns, Pablo Picasso, Piet Mondrian, Jackson Pollock, Willem de Kooning, Cy Twombly, Gerhard Richter, and others. The sales are staggered around the Venice Biennale and Frieze New York, with Sotheby’s holding its contemporary evening auction on May 14 and Christie’s its 20th-century sale on May 18. Notable consignments come from the estates of S.I. Newhouse, former MoMA board president Agnes Gund, and dealer Marian Goodman.

Frieze New York 2026 Sales Report & Contemporary Art Market Trends

Frieze New York 2026 concluded with significant sales activity, as galleries reported strong demand for blue-chip contemporary works. The fair featured a mix of established and emerging artists, with notable transactions including major paintings by living artists and secondary market pieces. Dealers noted a cautious but steady market, with collectors focusing on high-quality, investment-grade works.

Michael Jackson Accessories Hit the Market Amid Biopic Buzz

GWS Auctions is offering nine pieces of Michael Jackson memorabilia in a May 2 sale, including a signed pair of the late singer's Florsheim loafers. The auction features 734 items from the collection of Prince Lorenzo de' Medici, with highlights such as a crystal-studded white glove from Jackson's 1984 Victory tour and Swarovski-embellished socks from his Dangerous tour. The loafers, authenticated by Jackson's assistant Rosemary Chavira, carry a starting bid of $7,500, and the sale coincides with the record-breaking opening weekend of a new Michael Jackson biopic.

Banksy’s Girl and Balloon on Found Landscape Sells for $18 Million

Banksy's painting *Girl and Balloon on Found Landscape* sold for $18 million (£13.3 million) at a Fair Warning auction held at Tiffany & Co.'s Landmark store in New York. The 2012 work, which reimagines a traditional pastoral landscape with the artist's iconic balloon motif, was purchased by an anonymous US bidder after a phone battle. The result places it among the three highest auction prices ever achieved for a Banksy artwork, surpassing *Sunflowers From Petrol Station* and trailing only *Game Changer* and *Love Is in the Bin*.