In 1981, when Donald Trump was transforming himself into a Manhattan real estate star, he reached out to Andy Warhol—the art world’s icon of bold color and fame. Trump wanted Warhol to create a series of paintings of his latest trophy: Trump Tower. It seemed like a high-profile pairing, a flash of Manhattan glamour to showcase the skyscraper. But Warhol’s entries in his personal diaries reveal that this collaboration quickly fizzled out, thanks to clashing personalities and Trump’s refusal to pay.

Trump arrived at The Factory to review the work, accompanied by his entourage, and Warhol was ready to impress. He’d chosen colors that suited his artistic eye, a palette he felt would make Trump Tower pop on canvas as much as it did on Fifth Avenue. But Trump wasn’t having it. Displeased, he commented that the colors Warhol chose didn’t match the pink and orange tones of his tower’s lobby. Trump’s team suggested Warhol should change the pieces to match their decor, presenting the artist with swatches of the building’s entrance colors to guide him.

Warhol, ever sharp-witted, saw this as a hollow request, as if Trump wanted “cheap” wall decor rather than distinctive artwork. He went along with the feedback, though it went against his instincts. Still, Warhol thought they might reach a deal—that is, until Trump’s interest evaporated entirely. He never paid Warhol for the paintings, leaving him with art that was commissioned, but ultimately unpaid and unappreciated.

This treatment lingered with Warhol. In his diary entry from 1984, three years later, he still recalled the insult: “I still hate the Trumps because they never bought the paintings I did of the Trump Tower.” Trump’s refusal to pay left a sting, turning what should have been a unique collaboration into a bitter memory.

Now, decades later, Warhol’s “New York Skyscrapers” series is headed for auction at Phillips, where the paintings are estimated at $500,000 to $700,000. While no one knows the amount Trump originally offered—if he even made a formal offer—the paintings’ value today is a far cry from the likely price Trump would have paid back then. Trump may have seen these works as dispensable decor, but time has given them a value that dwarfs what he would have spent.

In the end, this “deal” captures the essence of both men—Warhol’s visionary art and Trump’s infamous deal-making style. Warhol never forgot the cold shoulder, and the missed investment has become a poignant twist: an art deal that, in true Warhol fashion, says as much about the value of art as it does about the personalities involved.

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