Inside Donald Trump's Prenuptial Agreements With His Two Ex-Wives

As someone notorious for going to lengths to protect his wealth, Donald Trump leaves no stone unturned — and marriage uncontracted. While he has only tied the knot thrice, he has reportedly signed prenuptial agreements eight separate times. With his current wife, Melania alone, he's reportedly already had to deal with renegotiations three times. It's as if he's almost as committed to drafting prenups as he is to tending to his business empire.

To be fair, the former president has once winced over the notion of drafting a contract with his wives. "It's a hard, painful, ugly tool," he told New York Magazine. "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.'" Interestingly, Ron Filipkowski, a lawyer who had foreseen that Melania and Donald would eventually revisit their prenup, noted that the couple's marriage is "very transactional" (via Newsweek) from the get-go. It seems that Melania got her way, ensuring a secure financial future for her and her son Barron in case Donald ends up behind bars.

His ex-wives, however, haven't been as successful. His first and second wives, Ivana Trump and Marla Maples, reportedly attempted to challenge their respective agreements and ended up getting the short end of the stick.

Donald and Ivana Trump tied the knot in 1977 and welcomed three children throughout their marriage. The two weren't merely husband and wife — they were also business partners in every sense of the word, with Ivana being instrumental in expanding the Trump empire, leading the development of the Trump Tower, managing the Plaza Hotel, and serving as CEO for the Trump Castle, among others. "Donald calls me his twin as a woman," she told Vanity Fair in 1988.

However, their marriage came crashing down in 1990 when Donald was found to have had an affair with Marla Maples, who would eventually be his second wife. One would think that the divorce would be seamless given the existence of a prenuptial agreement, which they reportedly updated four times, but what ended up happening was the exact opposite. The Washington Post reported that Ivana was seeking an amount between $150 and $500 million for her contributions to the Trump businesses, which was much more than what was outlined in their last round of negotiations. She was initially set to have $25 million, their home in Connecticut, and custody of their kids. "Mrs. Trump seeks only a fair and equitable settlement of the fortune she and her husband have built for their family," Ivana's spokesperson said.

Despite contesting the agreement, Ivana ended up with way less. Per The New York Times, their settlement stipulated that she get $14 million, the Connecticut home, a Trump Plaza apartment, and access to Mar-A-Lago, in addition to $650,000 annual child support payments. "I'm very happy that this is behind me and I think it's a real positive step for everyone," Donald said.

Donald Trump eventually went on to marry Marla Maples, with whom he shares one child, Tiffany. They tied the knot in 1993 and split in 1997, just a few months shy of their fifth anniversary. It seems as though the separation was intentional. If they ended up separating after their 5-year milestone, Donald would have been obligated to pay her more.

According to Vanity Fair, Maples initially sought out $25 million, but Donald insisted on following their prenup, which stipulated a payout of only $1 million if they divorced within the first five years of their marriage. That's exactly what the model got, including another $1 million she could use to purchase a home. Even the $100,000 in child support payments for Tiffany came with several conditions. They would come to an abrupt halt the minute she turned 21, joined the military or the Peace Corps, or had been gainfully employed full-time. "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 told New York Daily News.

While Maples left the marriage disappointed, Donald appeared quite content with the outcome. "I wish Marla well," he said. "I'm glad it worked out so amicably." Sure, Donald, sure!