Inside Donald Trump’s ‘Hard, Painful, Ugly’ Prenuptial Agreements to Safeguard Wealth From Ex-Wives

When it comes to safeguarding his wealth, Donald Trump has apparently left no stone unturned, including making sure his marriages come with airtight prenuptial agreements. The former president has reportedly inked eight prenups across his three weddings. Even with his current wife, Melania Trump, he's already renegotiated their prenup three times. Donald wedded Ivana in 1977 and went on to have three children together. Eventually, when their marriage disintegrated in 1990 as he began his affair with Maples, Ivana's contributions were grossly undervalued as per the terms of their prenup.

Though initially set to get $25 million, a home, and child support, Ivana challenged for a $150-$500 million payout after their split. Despite having updated their prenup four times, she walked away with just $14 million in cash, property in Connecticut, rights to use Mar-a-Lago, and $650,000 annual child support. "Mrs. Trump seeks only a fair and equitable settlement of the fortune she and her husband have built for their family," said Ivana's spokesperson.

Donald's marriage to mistress Maples in 1993 was similarly fraught. Just days before their wedding, she was presented with a prenup stipulating a mere $1 million settlement if divorced within five years of marriage. Their split in 1997, conveniently just before hitting that five-year mark, meant Maples received exactly $1 million, plus funds for a home and limited child support. "After giving Donald two years to honor the verbal commitments he made to me during our 12-year relationship, I decided to walk away completely under the terms of our prenuptial agreement that had been placed before me just five days before our 1993 wedding," Maples said to New York Daily News.

His critics have pointed out that Donald's past marriages showcased a methodical approach to circumscribing any claims to his fortune, even from those who may have played key roles in creating it. Maples had sought $25 million, claiming Donald reneged on verbal commitments after their lengthy 12-year prior relationship. Yet he stuck firmly to the prenup's terms, leaving Maples feeling shortchanged while he remained 'glad it worked out so amicably.' Through multiple divorces, Donald repeatedly prioritized protecting his assets to an exacting degree via prenuptial agreements. 

Donald has also been open about finding prenups an unpleasant necessity, once describing the process as 'hard, painful, ugly,' as per New York Magazine. However, he felt they were a must: "Believe me, there’s nothing fun about it. But there comes a time when you have to say, ‘Darling, I think you’re magnificent, and I care for you deeply, but if things don’t work out, this is what you’re going to get.’” He also compared prenups to a 'crystal ball,' claiming that if a couple was able to negotiate a prenup and still ended up at the alter, then there was a good chance their marriage would also work out; otherwise, it wasn't meant to be.