Ivana Zelníčkova was born in communist Czechoslovakia, when travel was tightly restricted. One of the only legal ways for her to leave the country was to marry a citizen of another country. She married an Austrian ski instructor, Alfred Winklmayr, which allowed her to move to Austria. During their two-year marriage, they never lived together, didn’t build a household, or present themselves socially as a couple. It was a marriage of convenience. Ivana moved to Canada within weeks of her marriage after receiving her Austrian passport and dissolved her marriage in absentia from Canada. The Austrian court finalized the dissolution in 1973. The process was simple because the couple had no assets to divide and no children to fight over.

Ivana first moved to Montreal, and then to Toronto, where she began modeling and teaching skiing. Her modeling work brought her to New York with a group during the 1976 Winter Olympics. Her crew happened into a New York City bar when the 27-year-old Ivana met a 30-year-old Donald Trump, who offered to get them seats in the crowded bar if he could join them.

“I’m Donald Trump and I see you’re looking for a table," he said. "I can help you.”

Ivana joked to her friends that the good news was they’d get a table quickly, and the bad news was that Trump would be sitting with them. They hit it off; he drove her home alone that night, and they began dating soon after. They married the following year and became one of New York’s most visible power couples of the 1980s. They had three children, Donald Jr., Ivanka, and Eric.

The couple was married for 14 years, with the last two negotiating and fighting over the divorce. They had a prenuptial agreement with the following terms:

• Cash payout capped at $25 million. This was the maximum Ivana could receive under the agreement, regardless of Trump’s net worth.
• A limited property allowance. She would receive one residence, but not multiple properties.
• Child support obligations: Trump would pay child support, but the prenup capped the amount and tied it to his income at the time of signing.
• Restrictions on alimony: The prenup sharply limited or eliminated long‑term alimony.
• No share of Trump Organization ownership; Ivana would not receive equity in Trump’s businesses.

When the marriage collapsed in 1990, Ivana challenged the prenup on several grounds. She argued Trump had pressured her into signing revised versions and claimed the agreement didn’t reflect the lifestyle and wealth they built together.

Ivana eventually received a settlement, far more than the prenup allowed. Her final settlement included: $14 million in cash, a 45‑room Connecticut mansion, a Trump Plaza apartment, $650,000 per year in child support, and one month per year at Mar‑a‑Lago.

While Donald spent two years publicly embarrassing Ivana, including pushing the New York Post to run a headline, “Best Sex I Ever Had,” attributed to then mistress Marla Maples. Ivana was focusing on getting paid, which she ultimately did. Ivana agreed that she would not publish or share any diary, memoir, letter, story, interview, article, or description of her marriage. She agreed not to divulge any information about Donald Trump’s personal, business, or financial affairs or any material that could be considered a depiction of their relationship, fictionalized or not.

If she violated the agreement, all payments and benefits from the settlement could be terminated and Trump could seek a court injunction to stop her from speaking

Ivana attempted at one point to have the confidentiality clause removed, but Trump refused. A New York appellate court ruled the NDA fully enforceable.

Marla Maples

Let’s just say that Marla Maples relationship with Donald overlapped his marriage to Ivana. The divorce from Ivana was finalized in 1992. Marla gave birth to Tiffany Ariana Trump in October 1993, though Marla and Donald didn’t marry until two months later. Their relationship was brief but tumultuous, ending in 1997 and finalized in June 1999.

Donald made out much better this time, having learned from the Ivana settlement. Maples received approximately $2 million in cash, of which half was required to be used to purchase a home. Tiffany received $100,000 annually in child support until she turned 21. Trump later contributed to Tiffany’s education, though this was not required under his agreement. Marla was also prohibited from speaking about their marriage without Donald’s approval.

Melania

The relationship, such as it is, between Donald Trump and the former Melania Knavs is ongoing. Melania was born in what is now Slovenia, modeling in Europe before coming to America. Her move to the U.S. was facilitated by Paolo Zampolli, an Italian‑born modeling agent and businessman. He signed her to his agency, sponsored her U.S. work visa, and arranged for her to live in a shared model apartment in Manhattan. There are questions about whether she was allowed to work on her original Visa and about how she qualified for a “genius Visa,” but I’ll let others answer those.

Melania moved to New York City in 1996 and met Donald Trump in 1998 at a Fashion Week party. Her modeling agent, Paolo Zampolli, allegedly introduced them, though author Michael Wolff says they were introduced by Jeffrey Epstein. When they met, Melania was 28 and Donald 52. The couple married in 2005, and Melania obtained her American citizenship in 2006. She already had her green card from 2001, and marrying Trump didn’t expedite her immigration process.

Melania had one child, Barron, about 14 months into the marriage. While Barron was still nursing, Donald was found to have had relationships with both playmate Karen McDougal and pornstar Stormy Daniels. Trump told McDougal that he and Melania had separate bedrooms, which he said empowered him to sleep with other women.

Trump and Melania had a prenup that reportedly resembled the Marla Maples agreement much more than Ivana’s. The prenup reportedly provided a relatively small lump sum, limited alimony, and no ownership in the Trump businesses. There were provisions for any future children, similar to what Tiffany Trump got, according to reports. The original prenup was revised shortly after Trump became president, which wasn’t too long after the Access Hollywood video came out, where Trump described his womanizing, and when the nation learned of McDougal and Daniels. Melania had been publicly shamed, but she wasn’t going to be broke. Her new prenup called for more security for herself and Barron, but she was nowhere near finished.

Melania has pursued a small but lucrative set of branding and intellectual‑property ventures. Since 2016, she has filed for or maintained trademarks in jewelry, skincare, fashion accessories, charitable branding, and digital content. These filings cover the U.S., China, and the EU. They don’t all turn into products, but they help her monetize her name.

The 2024 Melania documentary got her paid. Amazon paid $40 million for the documentary rights, of which Melania reportedly received about $28 million from that deal.

Between 2021 and 2023, Melania launched her “Head of State” NFT collection, “The Vision Collection,” and Digital artwork tied to her White House fashion moments. These projects generated revenue, though exact figures are not public. They were structured through her own companies, giving her direct control.

After leaving the White House following Trump's 2020 election loss, Melania made a number of paid appearances at private events. She has participated in high‑dollar private dinners, charity galas, and closed‑door donor events. These are typically six‑figure engagements.

Melania has explored book deals, though she has not released a memoir. Publishing insiders have said she has been careful to negotiate terms that protect her privacy and maximize control. It hasn’t been confirmed that she has a confidentiality agreement not to talk about Donald, but it isn’t likely that Donald forgot after remembering with the first two wives.

Melania Trump isn’t going out dependent on Donald Trump’s handouts. She has made over $ 1 million on her own since 2016, not including the $28 million from the documentary.

Across four decades, the financial stories of Ivana, Marla, and Melania Trump reveal a consistent pattern: each woman entered Donald Trump’s world under different circumstances, but each left her own imprint on the evolution of his marital, legal, and financial strategies. Ivana negotiated from a position of strength during Trump’s rise, securing a settlement that reflected both her role in the empire and the era’s public scrutiny. Marla, arriving at a moment of financial strain and reputational volatility, accepted a far more restrictive agreement that protected Trump’s assets above all else. By the time Melania entered the picture, the system was fully refined — her original prenup was tight, controlled, and designed to minimize exposure. Yet she ultimately proved the most strategic negotiator of the three, leveraging timing, circumstance, and her position as the mother of Trump’s youngest child to renegotiate stronger terms and build her own quiet financial portfolio.

Taken together, the financial histories of Trump’s marriages form a kind of ledger — one that tracks not only the fortunes of a family but the lessons learned from each chapter. Ivana’s settlement showed Trump what he was willing to lose. Marla’s prenup showed what he was determined never to lose again. And Melania’s revisions showed how a spouse could still reshape the terms when the balance of power shifted. In the end, the story of the Trump wives’ finances is less about glamour or scandal than about leverage, timing, and the evolving architecture of wealth inside one of America’s most scrutinized families.

You could make the case that all of them sacrificed their pride. Trump cheated on them all: on Ivana with Marla, and on Marla with Melania. Melania has endured not only the McDougal and Daniels affairs but also Trump’s being found liable for sexual abuse to E. Jean Carroll. All of them should have known what they were getting into, especially the pair who were first mistresses before marrying Trump.

Maybe they all got what they bargained for? Though I suspect Ivana never counted on being buried behind the first tee of a golf course. Marla Maples was a rising actress and working model before becoming best known as “the other woman.” Her career never recovered. Melania is still enduring the hell that is Donald Trump, knocking away his hand every time he reaches for hers and sending him to his own room at night.