In 1981, novice real estate developer Donald Trump was still building the first project that would bear his name: Trump Tower, on Fifth Avenue. Years later, he would film “The Apprentice” and run his first political campaign there. He still has a home on the penthouse floors.

But more than forty years ago, to commemorate his new skyscraper, Trump wanted only the very best and most beautiful work of art for his lobby. That’s why he commissioned a series of portraits of the building from perhaps the most iconic living American artist of the time: Andy Warhol.

One of eight portraits from Warhol’s “New York Skyscrapers” series will be sold at auction at Phillips on Tuesday and could exceed its estimated sales price of $500,000 to $700,000, according to Robert Manley, vice chairman and co-head of Modern Art . and Phillips contemporary art department. Artnet was the first to report the auction.

The auction house arrived at that range after looking at comparable sales of Warhol images of cars and buildings, Manley said. How accurate will the estimate turn out to be?

“I was talking to a collector two weeks ago and his opinion was that if Trump lost, this wouldn’t sell and no one would buy it, and if Trump won it would sell for a huge price,” Manley said. “It remains to be seen what will happen, but we do have some initial interest.”

The painting’s backstory offers a glimpse into the New York City society of the 1980s, as well as what the two figures made of each other.

“I had to meet Donald Trump at the office,” Warhol wrote in his diary in April 1981. “Donald Trump looks really good.”

The artist and the mogul were introduced by Marc Balet, a former architect who, at the suggestion of their mutual acquaintance Fran Lebowitz, became art director of Warhol’s magazine ‘Interview’.

Balet was working on a catalog for the stores in the Trump Tower atrium, and Trump’s then-wife Ivana asked if he could get Warhol to take portraits of the building flanking the entrance to the residential floors, Balet said in an interview from his house. in Connecticut.

“It was so strange, these people are so rich,” Warhol wrote about Trump and his entourage after that first meeting. “They were talking yesterday about buying a building for $500 million or something like that. They raved about the Balducci’s lunch, but they just chose it. I think because they go to so many places that have food. And they didn’t have any drinks, they all just had Tabs. He’s a butch guy. Nothing has been arranged yet, but I’m going to make a few paintings and show them to them.’

After he was hired in the spring of 1981, Warhol visited Trump’s office to photograph the architectural model of the rising Trump Tower, and showed Balet early versions of the paintings – four in silver and four in gold, each sold as a set of images for $100,000. per set, Balet said.

Warhol incorporated gold glitter and cut-glass “diamond dust” into the paintings to make the tower sparkle and sparkle in the light, Manley said, channeling what he thought would be the building’s aesthetic.

But when the Trumps finally saw the paintings in August, the real estate mogul didn’t like them and never paid for them, Warhol wrote.

“The Trumps fell. … I showed them the paintings of Trump Tower that I had done. … (I)t was a mistake to do so many, I think it confused them,” Warhol wrote, adding that Trump was angry that the series was not color coordinated with the planned interior decoration.

“I think Trump is kind of cheap, but I understand that feeling,” Warhol wrote. “And Marc Balet, who set up the whole thing, was a little shocked.”

Balet remembered the event a little differently.

“They rejected the paintings because they felt Andy’s work did not meet Trump’s standards,” Balet said. “So then Andy took it out on me. He was furious that he had worked for nothing and was super mad at me, and then he got over it.

The artist transferred the paintings to a dealer in Switzerland, who later sold them to private collections, Manley said. Two of the works are now in the Warhol Museum in Pittsburgh.

According to the diary, Warhol seemed to carry the sting of that rejection all his life. At Roy Cohn’s birthday party in February 1983, Warhol ran into Ivana Trump.

“She came over and when she saw me she was embarrassed and said, ‘Oh, what happened to those pictures?’ and I had a speech in my head to tell her, and I didn’t know whether to give it to her or not, and she tried to get away and she did,” Warhol wrote.

A year later, Warhol was a judge at cheerleading tryouts for the New Jersey Generals, a football team that Trump had bought.

“I was supposed to be there at noon, but I took my time and went to church and ended up walking around there around 2 p.m. This is because I still hate the Trumps because they never bought the paintings I made of Trump Tower,” Warhol wrote.

“I didn’t know how to score. The girls didn’t look special because there were no spotlights on them,” he wrote. “Ivana voted for all the girls who looked like her.”

Months later, he repeated this sentiment: “I hate the Trumps simply because they never bought my Trump Tower portraits,” Warhol wrote in May 1984. “And I hate them too because the taxis on the top floor of their ugly Hyatt Hotel just got back. There’s so much traffic around Grand Central right now and it takes me so long to get home.”

Balet called Warhol a smart businessman and was surprised that the artist did not receive money for the paintings in advance.

“Andy was pretty cheap too,” Balet said. “So it was two cheaper people who dared to do it together.”

Balet was surprised when he heard that one of the Trump Tower paintings was for sale Tuesday, and even more surprised when he learned the estimated sales price.

“I should take a look at my Warhols and see if there’s anything I want to sell,” Balet said. “Maybe prices will all go up again.”