Andy Warhol's Trump Tower, left, Trump Tower in New York City, right.
Left: Andy Warhol's New York Skyscrapers, 1981. Right: Trump Tower in 2022. Photo: ©The Andy Warhol Foundation for the Visual Arts, Inc.; Beata Zawrzel/NurPhoto via Getty Images

Andy Warhol’s painting of Trump Tower is heading to auction in New York next month, two weeks after Election Day.

Estimated at $500,000 to $700,000, New York Skyscrapers will be offered during the evening sale at Phillips on November 19. Shimmering with so-called “diamond dust,” it was commissioned by Donald Trump in 1981 to celebrate his first ground-up development in Manhattan.

Warhol first mentions the real estate mogul and his first wife, Ivana, in his posthumously published diaries on February 22, 1981, after meeting the couple at a birthday party. 

Two months later, Marc Balet, the art director of Interview magazine, arranged for Trump to visit Warhol’s Factory. Trump, whom Warhol described as “butch,” was interested in having the Pop artist make a portrait of his forthcoming skyscraper on Fifth Avenue.

Andy Warhol’s New York Skyscrapers (1981). Courtesy: Phillips

“Had to meet Donald Trump at the office (cab $5.50),” Warhol wrote on April 24, 1981. “Marc Balet had set up this meeting. He’s designing a catalogue for all the stores in the atrium at the Trump Tower and he told Donald Trump that I should do a portrait of the building that would hang over the entrance to the residential part. So they came down to talk about that… Nothing was settled, but I’m going to do some paintings, anyway, and show them to them.”

Designed by architectural firm Der Scutt of Swanke, Hayden, Connell, and Partners, the building was still under construction. So, Warhol based the paintings on the model of what would become the 58-floor Trump Tower. After photographing it, Warhol created multiple silkscreen canvases, in black, silver, and gold hues. To convey glitz and affluence, he sprinkled the wet paint with ground glass, known as “diamond dust,” a material that he began using in the early 1980s. 

In August, the Trumps returned to the Factory to look at the paintings. They didn’t like what they saw.

“I don’t know why I did so many, I did eight,” Warhol wrote on August 5, 1981. “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. They have Angelo Donghia doing the decorating so they’re going to come down with swatches of material so I can do the paintings to match the pinks and oranges. I think Trump’s sort of cheap, though, I get that feeling.”

Warhol never got paid for his efforts, and he seemed resentful about the failed commission. When he ran into the Trumps again in 1983, he described Ivana as “embarrassed.”  

“Oh, whatever happened to those pictures?” she asked Warhol, according to his diary entry on February 26, 1983. “And I had this speech in my mind of telling her off, and I was undecided whether to let her have it or not, and she was trying to get away and she did….”

After Trump Tower’s completion in November 1983, Warhol was invited to judge cheerleading tryouts there.

“It was the first tryout, and I was supposed to be there at 12:00 but I took my time and went to church and finally moseyed over there around 2:00, “ the artist wrote on January 15, 1984. “This is because I still hate the Trumps because they never bought the paintings I did of the Trump Tower.”

New York Skyscrapers ended up in the collection of Warhol’s Swiss-based gallerist and close friend, Bruno Bischofberger, who included it in an exhibition, “Gems & Skyscrapers,” at his Zurich gallery in 2001. It was acquired from Bischofberger by the anonymous collector, who is now offering it at Phillips, according to the auction house.