In the fall of 1993, Donald Trump was clawing out of the rubble of a cratering business career. Three of his Atlantic City casinos had gone bankrupt. He’d nearly defaulted on $3.4 billion in debt, and, humiliatingly, his creditors had put him on a living allowance: $450,000 a month. Bankers forced him to sell his 282-foot yacht, the Trump Princess, as well as the Trump Shuttle airline and stake in the Plaza hotel, which Trump had once called “the ultimate trophy in the world.” His relationship with Marla Maples had begun in Trumpian glory, with the words “Best Sex I’ve Ever Had” on the front page of the New York Post, but Maples had just given birth to their daughter, Tiffany, and was eager to get married. “I’m going to have to make a decision about Marla...what should I do?” Trump asked his mother around this time. He was 47 years old. Many people in the city believed he was finished.
A source recently passed me a revealing document from this era: Trump’s prenuptial agreement with Maples. Its draconian terms suggest a penuriousness at odds with his public image as a free-spending billionaire in his gilded triplex penthouse. And its confidential financial statements included in the agreement is a sketch of Trump’s immense privilege and the wealth he squandered, telling in both what it illuminates and what is obfuscates.
From the V.F. Archive: Marla Maples and The Heart of the Deal
With Trump fighting House Democrats over the release of his tax returns, what we know about his opaque financial life has largely come from a paper trail unearthed by investigative reporters. Journalists at The New York Times have blazed much of this difficult terrain with bombshells such as the revelation that his father, Fred, bequeathed Trump more than $400 million in today’s dollars, and that IRS tax receipts indicate Trump lost more than more than $1 billion between 1985 and 1994. Dogged reporting by the Times and others revealed Trump’s core argument for being president—he’s a self-made billionaire who alone can solve the world’s most intractable problems—to be as credible as a degree from Trump University. But the deal he made with his second wife was, as a business proposition, a raging success, even though as a personal matter, it was as ugly as could be.
Even Donald Trump realized that, when it comes to romance, a prenup is a buzzkill. “A prenuptial is a horrible document,” he once told a reporter, “because it says, ‘When we get divorced, this is the way we’ll split things up.’ And when you’re a believer in positive thinking, it isn’t good. But it’s a modern-day necessity.”
Raoul Felder, the legendary divorce lawyer whose clients have included Trump’s own lawyer Rudy Giuliani, agreed. “A prenup sucks romance out of the relationship,” he told me. “It’s a prior agreement as to the disposition of money, assets, payments. You basically plan the divorce before you get married.”
Prenup negotiations require both parties to disclose to the other how much money they have. In the document, Trump stated he was worth $1.17 billion; Maples had $100,000 in the bank. But while Trump presented himself as a Master of the Universe, back and bigger than ever, he was, in all likelihood, not an actual billionaire when he signed the agreement. (He didn’t appear on the Forbes list between 1990 and 1995.) And Trump had financial incentive to inflate his wealth: if he understated his fortune, Maples could later claim in a divorce that Trump hid money from her at the time, which could void the prenup’s terms. “When you’re doing a prenup, the worry is you understate your assets. If you overstate it, then you’re protected,” a high-profile Manhattan divorce lawyer told me.
To keep himself in the nine-figure club, Trump provided extremely optimistic values for his real estate assets. For instance, he stated the Taj Mahal was worth $1.25 billion, even though it had trouble making debt payments virtually from the moment it opened. (In 2017 it sold for 4 cents on the dollar.) He valued the Trump Castle and Trump Plaza casinos $450 million and $650 million, respectively. (Both went bankrupt in 1992.) Trump’s accountants at Spahr, Lacher & Sperber didn’t vouch for his fuzzy math. “We have not audited or reviewed” the numbers Trump provided, they stated in a note attached to the financial report. They added: “Assets are presented at current values estimated by Trump using various valuation methods.”
The White House did not respond to multiple requests for comment.
Trump, of course, overstated his net worth and business acumen since his first forays into Manhattan real estate in the 1970s. In a 1976 interview with the Times, he claimed to be worth “more than $200 million” when, in fact, he reportedly had taxable income of only about $75,000 in 1975. In subsequent years, he posed as a Trump Organization official to mislead Forbes editors, so they would include him on the magazine’s annual list of billionaires.
More than anything, the prenup shows how fiercely Trump wanted to protect the money he did have. Maples reportedly wanted $25 million, but Trump agreed to pay her only $1 million if they separated within five years, plus another $1 million to buy a house. Trump also would stop making $100,000 child support payments for Tiffany when she turned 21. The agreement states that Trump’s payments would cease earlier if Tiffany got a full-time job, enlisted in the military, or joined the Peace Corps. “The way it was drawn up is ironclad and shows how wary he was,” Felder told me after reviewing the prenup. “He was leaving nothing to chance.”
Maples agreed to these terms with the hope that Trump would renegotiate a better deal in five years. “We basically came to an agreement that for the first few years we would agree on something and then tear it up,” she told a journalist. “She was telling people it was love,” said a source who knew the couple well. Ultimately, Maples didn’t have much of a choice if she wanted to get married—which she desperately did. When she traveled, she brought along her wedding dress, so that she would be ready at a moment’s notice if Trump said he wanted to get married, said the source. Maples declined to comment.
Marla Maples entered Trump’s life as his marriage to Ivana was crashing. They bumped into each other on Madison Avenue. Maples was Ivana’s opposite in almost every way, a difference that the tabloids mined in their endless coverage of the domestic soap opera. Where Ivana was the austere European with royal aspirations, Maples was a beauty queen from the Bible Belt. “I’m, like, of the soil, of the country, of a solid, firm belief in God,” Maples told Vanity Fair in 1990. The only daughter of a small-time subdivider turned Elvis impersonator, Maples came to New York in 1985 in her early 20s, with celebrity dreams and a kooky spirituality that was both Christian and New Age. “A psychic told me I’m just a little girl inside this grown-up body,” she said in the 1990 interview with V.F. “That’s what makes me feel uncomfortable—I forget I have this body. I’m just a little girl.” The source close to the couple told me she was out of her depth in Trump’s world. “It’s a sad story. She really didn’t know how to handle him,” the person said.
Trump and Maples’s relationship was at a crossroads after Trump and Ivana divorced in 1992. At one point, he broke up with Maples by FedEx-ing her a letter, the source said. Trump bragged about his bachelorhood. “I had been in Europe fucking every model in the world. My life was wild,” he told Vanity Fair in 1994. But Trump, a famous germophobe, also found monogamy reassuring as the AIDS crisis raged. “Being single out there is a little bit scary, to put it mildly,” he said. “It’s like being in Vietnam, in the forests, and knowing there are guns pointed at your head.”
Two factors—one personal, the other professional—ultimately led Trump to propose to Maples. On October 13, 1993, Maples gave birth to Tiffany. Trump’s conservative parents were upset that he’d fathered a child out of wedlock. But the bigger problem was that it likely complicated Trump’s plan to rid himself of his failing casinos. At the time Tiffany was born, Trump was preparing to take his casinos public to raise cash to pay down his debts. His tabloid domestic life spooked Wall Street and diminished his chances for an IPO. Marrying Maples would calm investors.
But before marrying, Trump needed Maples to sign a prenup. His divorce with Ivana had been a legal war. (In March 1990, Ivana sued Trump for $2.5 billion to nullify a revised version of the prenup that Trump’s lawyer, Roy Cohn, had drafted back in 1977.) Ultimately, Trump and Ivana settled for $14 million. (Ivana took the deal because her team worried Trump was going bankrupt.) In addition, Trump gave Ivana their Greenwich estate and agreed to pay $650,000 annually to support Ivanka, Eric, and Don. Jr. Trump wanted to make sure Maples couldn’t come after his money.
Convincing her wasn’t easy. “This was the big battle all along,” Maples told Vanity Fair at the time. But Trump persisted and Maples relented, telling a journalist that she would renegotiate the agreement in five years. Trump hired the lawyer Stan Lotwin to draw up terms. Maples was represented by the New York lawyer Sharon Stein. Maples tried to hold out for better terms, but Trump utterly refused to budge, the source told me. He held the line up their wedding day at the Plaza, said the source. “Marla was under duress. Donald’s position was: without the prenup he wasn’t going to get married.” With 24 hours to go before a thousand guests arrived, Maples caved.
The stringent agreement Maples signed reflected the degree of leverage Trump had over the Georgia-born beauty queen whose most valuable asset was the $250,000 engagement ring Trump bought her. “What was she going to do? She would have taken whatever he said,” Felder told me. According to the prenup, Maples surrendered any claim to Trump’s future income and inheritances. The $1 million award Trump would pay her was it. (There would be no alimony.)
Having protected his money, Trump designed the agreement to also protect his image. His divorce with Ivana played out in public, and Trump was determined to keep Maples quiet. Under the extensive confidentiality agreement, Maples agreed she wouldn’t publish “any diary, memoir, letter, story, photograph, interview, article, essay, account or description or depiction of any kind whatsoever, whether fictionalized or not, concerning (or seeming to concern) the details of the parties’ marriage.” And if she did, the prenup stated: “Donald will suffer irreparable damage and injury in the event of any such breach.”
As for Maples’s plan to renegotiate a better deal after five years of marriage, she and Trump separated after only four. The divorce was messy. Ironically, it was triggered by a May 1996 National Enquirer cover. “Shock for Trump! MARLA CAUGHT WITH HUNK” blared the headline for an article revealing how Palm Beach police caught Maples during a “frolic” on the beach at 4 a.m. with a Trump bodyguard—an account that both Trump and Maples denied. Trump went nuclear over the article, said the source. But he didn’t want to divorce Maples right away, because it would make him look like he’d been cheated on. “He bided his time,” the source said.
Trump and Maples separated the following year. Maples moved to California where she raised Tiffany, and largely stayed out of public view. But during the 2016 campaign, she thought about breaking her silence. According to the source, she wrote a memoir that would detail the marriage. She even had spoken to a publisher, the source said: Judith Regan. (Regan did not respond to a request for comment.) But Maples got cold feet after a Trump Tower meeting with Donald and Ivanka. “They really double-teamed her. They got her not to write the book,” the source said.