All Of Donald Trump's Prenups Explained

Donald Trump has always been a businessman first, and this profession has permeated his relationships, politics, and marriages. Trump might not be nearly as successful a business mogul as he'd like the world to believe, but the man knows how to hold on to his money. One way he's done that, according to some accountants who spoke to The Guardian in 2020, is by evading taxes. Trump, despite being a billionaire, only paid a meager $750 in federal income tax in 2016. "[He's either] a very bad businessman or a tax cheat ... probably both," one expert surmised.

Aside from good old tax evasion, Trump has used other methods to hold on to his riches. When a man like him gets married, there's always the risk that the Mrs. Trump in-waiting is only marrying him for his money. So with all three of his marriages, Trump ensured his new wife signed a prenuptial agreement. This allowed the former "Apprentice" host to control how much his wife could get from him should the marriage fizzle out. Like everything else in life, one gets better at prenups the more you have to draw them up, and Trump (and his lawyers) learned a lesson or two from the president's first prenuptial agreement with Ivana Trump, who arguably managed to get much more out of her ex-husband than he ever intended.

Marla Maples and Melania Trump's prenups were almost certainly affected by the mess of the former real estate mogul's first divorce. When assessing how much Trump's divorces really cost him, it's clear Ivana's antics caused the second Mrs. Trump, Marla Maples, to walk away from her marriage with the bare minimum (if $1 million could be considered as such), and rumor has it Melania got the same treatment — in the beginning, anyway.

Donald Trump and Ivana Trump's initial prenuptial agreement was pretty brutal. It included a clause that stipulated that anything her husband gave her was, in reality, not Ivana's; she'd have to return any gifts, whether it be jewellery, expensive clothes, or cars. Ivana was, understandably, upset. Donald blamed it on his bloodthirsty attorney Roy Cohn, telling his wife, "It is just one of those Roy Cohn numbers" (via the Houston Chronicle). He subsequently had the clause removed from the prenup.

The clause came up again during the couple's divorce, with Ivana explaining how upset she was by her husband's blatant stinginess, telling the court, "I remember the part about the gifts. I had been very hurt. I had been confused by it. ... I didn't understand the whole concept, why I'm returning the gifts which are going to be acquired by my husband and given to me during our marriage" (via New York Daily News). She also touched on another incident where Donald proved he wanted to part with as little money as possible, even if he happened to die. Ivana asked him to make some changes to the prenuptial agreement that would dictate her assets should this become a reality. "My husband told me he can't do that because he would have to pay a gift tax, which I never checked, but obviously it was a lie," Ivana said in the deposition.

It might be safe to say that Donald Trump underestimated his first wife, Ivana Trump. For those wondering how much money Ivana got from Donald after their messy public divorce, the answer is plenty. Ivana, who was Catholic, didn't want to divorce her husband despite his affair with Marla Maples, according to her lawyer. Donald, however, was ready to move on, and Ivana wanted her fair share.

The couple's prenup, which was updated a few times throughout their marriage, stipulated that Ivana was entitled to $15 to $20 million and some of her husband's properties. Amid the messy divorce, Ivana claimed her former lawyer had misled her when it came to how much she was entitled to. Her lawyer, Lawrence Levner, was appointed to Ivana by Donald's personal lawyer, Roy Cohn, and Ivana's new attorney used this as leverage to petition the existing prenup, arguing she didn't have proper representation when the prenup was drawn up. The late Mrs. Trump's new attorney, Michael Kennedy, asserted that Ivana was entitled to $2.5 billion. Donald, of course, disagreed.

In the end, Ivana only managed to get $14 million from the divorce, paired with a Trump Plaza apartment and a 45-room mansion in Greenwich, Connecticut. She was also allowed to spend one month per year at Mar-a-Lago and received annual child support of $650,000.

Thanks to Donald Trump and Ivana Trump's marriage going down in history as one of the most troubled Trump family marriages, the former "Apprentice" host made sure his second marriage with Marla Maples had an ironclad prenup. Plenty is known about the couple's prenuptial agreement, thanks to a source who passed the document to Vanity Fair in 2019. Trump has called the legal agreement a "horrible document" but "a modern-day necessity."

In his prenup with Maples, which reportedly had the latter in tears, Donald drove a hard bargain. He wasn't about to make the same mistakes he did with Ivana's prenup, and so he overstated his value in the agreement as a means to ensure Maples couldn't contest the prenup in court by claiming he'd hid any money from her. Maples wasn't shy about what she wanted, and requested the document dictate she get $25 million in case of a divorce. Trump only granted her $2 million — half of which would be for a house. The agreement dictated that Trump would pay $100,000 to Maples in child support for their daughter, Tiffany Trump, but that these payments would cease once she turned 21. Donald also dictated that he could end child support in the event of Tiffany joining the Peace Corps, the military, or if she managed to get a full-time job before the age of 21. Marla had hoped to renegotiate the prenup in five years, but the couple's marriage didn't even last that long, and she walked away with a meager $1 million.

Once you start digging, you'll find that Donald Trump and Marla Maples' divorce wasn't as messy as one might've thought. This was likely because Maples didn't have a leg to stand on when it came to contesting her prenup, unlike Ivana Trump. Still, longtime pundits might wonder why Maples has never released a memoir of her own detailing her time as Mrs. Trump. As it turns out, it wasn't for lack of trying; that prenup Maples signed so long ago still holds sway over her to this day.

The couple's prenuptial agreement prohibited Maples from publishing "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" (via Vanity Fair). Maples still tried, attempting to publish a memoir titled "All That Glitters Is Not Gold" in 2001. The book never made it into the hands of curious readers. Maples had another go at it around Trump's 2016 presidential run, teaming up with a ghost writer to chronicle her marriage — and affair — with Trump in "It's About Time."

Because of her prenup and a pesky non-disclosure agreement, this tome never saw the light of day either. Maples attempted to get Trump's permission to publish, but, unsurprisingly, didn't manage to acquire it. A source told Vanity Fair that Trump called in his daughter, Ivanka Trump and "double-teamed her [Maples]. They got her not to write the book."

Not much is known about Donald Trump and Melania Trump's prenup. It is, after all, supposed to be a private document, but when high-profile couples divorce, these agreements tend to leak. Since there are many possible reasons why Donald and Melania stay together, it's likely the public won't glean any details about their prenup anytime soon. The little we do know, however, indicates that the president was initially as ungenerous with Melania as he was with Marla Maples.

In her book, "The Art of her Deal," celebrated Washington Post reporter Mary Jordan did a deep dive into Melania's life — and her marriage. In the tome, Jordan claimed the first lady's initial prenup left much to be desired, but she bided her time, and when Trump was faced with various allegations of sexual misconduct ahead of the 2016 presidential election, Melania took her shot and renegotiated her prenup. Jordan writes that the first lady, for the most part, did so to favor her son, Barron Trump. "She wanted proof in writing that when it came to financial opportunities and inheritance, Barron would be treated as more of an equal to Trump's oldest three children," she penned.

Melania's former chief of staff, Stephanie Grisham, decried the claims made in the book as fake news after its release. "Yet another book about Mrs. Trump with false information and sources. This book belongs in the fiction genre," Grisham said in a statement (via CNN). It's worth noting that Grisham eventually published her own book, which confirmed some of the things she claimed to be fiction in Jordan's tome.

The year 2016 wasn't the last time Melania Trump renegotiated her prenup. As Donald Trump's New York fraud case woes just kept piling up, the first lady was reportedly concerned that the sordid legal affair would bankrupt her husband — and her — if she didn't take action to prevent it. "This agreement was necessary because of the current legal battles ... [Donald] has suffered," a source told Page Six about the renegotiated prenup in September 2023. They added that this was the third time Melania has revised it, and she managed to get Donald to part with more money and property in case of a divorce. She also ensured, again, that Barron's trust fund continues to maintain a healthy balance.

Melania's noticeable absence at Donald's side as he announced his reelection bid had tongues wagging. Former federal prosecutor and Meidas Touch's editor-in-chief, Ron Filipkowski, predicted that Melania will likely only make an appearance once she'd renegotiated her prenup with Donald. "There was no doubt in my mind that he sweetened the prenup to get her to do the bare minimum and just go out and give one five-minute interview to Fox [News]," Filipkowski said on a YouTube livestream (via Newsweek) after news of the renegotiated prenuptial agreement broke.

The source who spoke to Page Six said that Melania didn't exactly tell Donald she'd abandon him if he didn't give in to her demands, but she also didn't not say it. "It's not that she threatened to leave him. It's definitely the underlying idea," the source disclosed.