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On November 19, Andy Warhol’s New York Skyscrapers will go up for auction at Phillips, with estimates ranging from $500,000 to $700,000. Commissioned in 1981 by Donald Trump to mark his first Manhattan skyscraper, the artwork shimmers with Warhol’s signature “diamond dust”—ground glass used to give his canvases an air of opulence.

Warhol first noted Trump and his then-wife, Ivana, in his diary on February 22, 1981, after encountering them at a party. Soon after, art director Marc Balet, organized a visit for Trump to Warhol’s famed Factory studio. Describing Trump as “butch,” Warhol wrote that the young real estate developer was interested in a Warhol portrait of his upcoming skyscraper on Fifth Avenue, designed by Der Scutt of Swanke, Hayden, Connell, and Partners. With the building still under construction, Warhol photographed the architectural model and created multiple silkscreen canvases in black, silver, and gold, dusting them with diamond dust for added glamour.

When the Trumps returned to view the completed works in August, however, they were unimpressed. In his diary entry from August 5, 1981, Warhol recalled the meeting: “I don’t know why I did so many; I did eight…in black and grey and silver, which I thought would be so chic for the lobby. But it was a mistake to do so many; I think it confused them. Mr. Trump was very upset that it wasn’t color-coordinated,” he wrote. Warhol added that the Trumps had their interior designer, Angelo Donghia, suggest swatches in pinks and oranges to better match the building’s decor. Warhol noted his reservations, quipping, “I think Trump’s sort of cheap, though; I get that feeling.”

Warhol’s paintings never found a home in Trump Tower, and he never received payment for the commission. The artist later mentioned a strained encounter with Ivana Trump in 1983, noting that she seemed “embarrassed” and inquired about the artworks. Warhol recorded in his diary that he contemplated giving her a piece of his mind but ultimately refrained.

The project’s fallout lingered with Warhol, who was invited to Trump Tower in January 1984 as a judge for cheerleading tryouts—a favor he approached with indifference. “I still hate the Trumps because they never bought the paintings I did of the Trump Tower,” he wrote.

New York Skyscrapers eventually landed in the collection of Bruno Bischofberger, Warhol’s Swiss gallerist and friend, who exhibited it at his Zurich gallery in 2001. The piece, later sold to an anonymous collector, is now being offered at Phillips. The auction represents a return to the spotlight for this piece, emblematic of the intersection of art, real estate, and Warhol’s sharp social commentary.