Ivana Trump: Right-hand mogul or window dressing?

Close your eyes and think of Ivana Trump, and you will likely conjure up an image of the quintessential 1980s Manhattan socialite: glamorous, loud, filthy rich and possessed of an insatiable energy emblematic of the era. Ivana was, in her heyday, such a tabloid darling and celebrity magnet that a biopic of her life may well have been called “Everything Everywhere All at Once.”

Less heralded are the Czech American’s contributions to Donald Trump’s real estate empire, and by extension, the New York skyline. Back when Trump was a real builder, putting up showstopping projects across Manhattan and transforming the public’s perception of what a developer could be, Ivana was right there with him. She epitomized the Fifth Avenue lifestyle the Trump Organization marketed to prospective buyers.

“Ivana and Donald were made of the same sperm,” said Louise Sunshine, the longtime new development chief for the Trump Organization in Manhattan. “Their personalities and their drive and their determination were equally matched.”

Ivana died last week at the age of 73, after what medical examiners said was a fall in her Upper East Side home. Though news outlets in the wake of her death credited her as an important player in the Trump Organization, the extent of her role remains a matter of debate. Several people familiar with the company during the Ivana era said that although she played a key role in one of the company’s flagship projects, the Plaza Hotel, on other projects she was little more than window dressing and a press magnet.

“I was there a lot,” said one real estate veteran who helped shepherd Trump through his troubles with lenders in the 1980s and 1990s. “I could have been in his [Donald’s] office, three, four days a week. I really didn’t interact with her. She wasn’t in meetings.”

In many cases, the idea of Ivana was more important than her material contributions.

“She was part of Trump’s Potemkin village,” said Charles Bagli, New York’s longest-serving real estate reporter. Bagli noted that when his former newspaper, the New York Times, gave Ivana’s death the front-page treatment, describing her as a “businesswoman,” he was taken aback.

“I was sort of like, ‘what business?'” Bagli said.

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Ivana Trump (Illustration by The Real Deal with Getty Images)

Ivana, a competitive skier and model, met Trump in 1976 and married him in 1977. Her husband had recently acquired the Commodore Hotel at 109 East 42nd Street, near Grand Central Terminal, by means of a controversial tax abatement (in 2020, ProPublica reported that the abatement had cost the city $410 million).

Having secured Hyatt as a partner, he began redeveloping the hotel. At the Trump Organization, real estate is very much a family business, and Ivana threw herself in. She spent 10 hours a day at the Commodore site, according to an account she gave Vanity Fair in 1988, touching base with electricians and contractors, calling the shots on “every pillow, every table and chair, and every brass column.”

“She thinks and talks numbers like a platinum-blond computer,” wrote Vanity Fair’s Michael Shnayerson in the article, headlined “Power Blonde,” an account of her post-wedding rise and her time managing Trump’s Castle, a casino in Atlantic City. “The numbers are money, and the money is big.”

“Ivana and Donald were made of the same sperm. Their personalities and their drive and their determination were equally matched.”

Donald saw things at the Commodore, which became the Grand Hyatt, a little differently. “I would send over one of my executives, or more often my wife, just to see how things were going,” he wrote in his autobiography “Trump: The Art of the Deal.”

Chatter of Trump as a potential White House occupant had already begun to bubble up. When Shnayerson asked Ivana about it, and about her own ambitions to be First Lady, she replied that it was out of the question — at least for a decade.

“There is so much to do,” she said. “We have invested in this town close to a billion dollars. We can’t just put it in escrow and go to the White House. It would go down the drain in a second.”

From left: Macaulay Culkin and Donald Trump at the Plaza in “Home Alone 2: Lost in New York” (screengrab)

America’s most famous hotel

In 1988, Donald Trump made his boldest acquisition in New York, paying just under $400 million in a highly levered deal for the Plaza, the Fifth Avenue symbol of wealth and glamor that’s been dubbed “America’s most famous hotel.”

He told reporters he would embark on a major upgrade of the 1,000-key landmarked hotel and said he planned to name Ivana the president of the project. Her compensation? $1 a year, “plus all the dresses she can buy,” he told the Times.

“Donald is not the most generous of people,” said Sunshine, who had her own tussles with the mogul over compensation. “He probably thought she didn’t deserve a salary.”

By all accounts, Ivana was a key player in the project. “I truly felt like she was the person running it,” said the associate who advised Trump throughout that era. “She was very much involved in the operation, redesign and renovation.”

Trump had hoped to convert the property into condominiums, then sell enough units to help pay down some of the debt, the associate said. “If you were able to sell 25 percent of the apartments at a decent price, including some of the suites, it paid down the debt, reduced carrying costs, and it would still operate.” However, “the condo conversion didn’t happen because we were going through the restructuring, and nothing was being converted.”

Ivana Trump (Illustration by The Real Deal with Getty Images)

Donald and Ivana split in 1990 in a divorce that was the tabloid event of the season. As for the Plaza, Donald was eventually forced to hand over control of the property to his lenders, who in turn sold the trophy to a partnership between Saudi Prince Alwaleed bin Talal and Singapore billionaire Kwek Leng Beng.

In the Times’ obituary, Ivana was described as “an equal if behind-the-scenes partner in Mr. Trump’s business.”

“She emphasized opulence,” the paper’s Clay Risen wrote. “It was she who chose the pink marble and gleaming brass of Trump Tower, on Fifth Avenue. Though she insisted that her husband was the boss, it was also clear that she was among his closest confidantes — advising him, for example, on his decision to go into the casino business in Atlantic City.”

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It’s a characterization that those within Trumpworld at the time, though they spoke highly enough of Ivana, might take issue with.

“It wouldn’t surprise me if she was talking to Donald,” said the Trump adviser. “It’s hard to know — Donald has this amazing quality of tuning out everything he doesn’t want to hear.”

Sunshine, who handled sales at Trump Tower, said she didn’t recall Ivana being that involved in that project. Though she praised her for overcoming adversity, fleeing life behind the Iron Curtain and making it to the top of Manhattan, the hierarchy at the Trump Organization, Sunshine said, was clear.

“Donald was Donald,” she said. “He was always Donald. There was only one person in Trumpworld.”