The Horrible Event That Almost Left Donald Trump Penniless

During the early 1990s, Donald Trump hit a low point financially. Plus, his marriage was on the rocks when it was leaked that he had been having an affair with model Marla Maples. Donald and Ivana Trump’s marriage crumbled in a divorce that nearly left him penniless. Here’s how much financial trouble Trump was actually in plus how much his messy divorce really cost him.

There were rumors about Donald Trump cheating long before the divorce

Donald and Ivana Trump

Trump had a reputation for being a womanizer. | Swerzey/AFP/Getty Images

A few years before the scandal broke about Donald Trump’s affair with Marla Maples, friends of Trump said he was bored with his wife, Ivana. According to Newsweek, Trump was rumored to have many mistresses, including actresses, ice skaters, and even friends of his wife. None of the rumored affairs were proven — all women denied the accusations.

Next: Maples wasn’t allowed to be seen with Trump. 

Trump kept Marla Maples hidden

Marla Maples and Donald Trump

Trump hid Maples around his properties. | Diane Freed/Getty Images

It wasn’t long before Trump actually did stray from his wife. He met Marla Maples in 1985, but the affair didn’t start until 1988. Trump hid Maples in places like his Southampton beach house and his yacht, Princess Trump. Their dates occurred in his limo for fear of her getting in the way of his very publicized marriage to Ivana Trump. But Ivana Trump was well-aware of her husband’s affair.

Next: Ivana Trump and Maples met in a surprising way. 

Around Christmas of 1989, there was a confrontation between Ivana Trump and Maples

Ivana Trump confronted Marla Maples. | AFP/Getty Images

The Trump family was vacationing in Aspen in December, and as it turned out, Maples was there, too. Ivana Trump and Maples had a scary confrontation; the wife and mistress had an intense conversation at lunch about how both of them loved Donald Trump. According to Ivana Trump, Donald Trump said nothing during the conversation. “And that’s how I found out,” she told Barbara Walters in a 1991 interview.

Next: Ivana and Donald Trump didn’t decide to divorce right away. 

The couple didn’t discuss divorce until more than a month later

Donald and Ivana Trump in a Pizza Hut commercial

The couple were a pop culture staple until the divorce. | The Daily Conversation via YouTube

It wasn’t until February 1990 that the couple finally decided to discuss their divorce. In early February, Donald Trump told his wife that he was leaving her just before he got on a plane to Tokyo. According to Newsweek, he hired a spokesperson to speak with the reporters; he claimed that the marriage between him and Ivana “just was not working out.”

Next: Rumors swirled about the couple’s divorce settlement. 

Reports said that Donald Trump might settle for around $100 million

Trump was in terrible financial shape before the divorce. | Global TV via YouTube

Initial reports suggested that Donald Trump might settle with Ivana Trump for $100 million. The rumor was that Trump wanted a quick settlement so that he could continue his budding romance with Maples. However, the tabloids didn’t realize how much financial trouble Trump was in when the divorce began.

Next: The prenuptial agreement had been edited multiple times after their marriage.  

Ivana Trump had reportedly signed a $25 million prenuptial agreement

Ivana Trump

Ivana Trump signed a very valuable prenuptial agreement. | Joe Klamar/AFP/Getty Images)

Reportedly, Ivana Trump had signed a prenuptial agreement that granted her custody of the children, one vacation home, and not more than $25 million, Newsweek reported. But apparently, Donald Trump edited the agreement four times throughout their marriage. By the time the divorce actually happened, Ivana was no longer content with only $25 million.

Next: Ivana Trump decided she was worth more.

Ivana Trump wanted to overturn the prenup

Donald and Ivana Trump

The couple had a bitter divorce. | Dave Kotinsky/Getty Images

Four documents were created when the Trumps were together – one pre-nuptial agreement and three post-nuptial agreements. And the settlement would depend on each of those. Ivana Trump said she deserved far more than $25 million because she helped build Donald Trump’s empire into what it was. However, lawyers said Ivana Trump’s hope of overturning the agreement was lost unless she could prove that she was either deceived or forced to sign.

Next: Trump’s financial problems came to a head during the divorce. 

Trump was not worth nearly what his wife thought he was

Taj Mahal Trump Hotel And Casino

Trump’s bad business deals forced him to bankruptcy. | Craig Allen/Getty Images

It was quickly realized that Donald Trump was not worth nearly the amount that Ivana Trump believed. In fact, the once-billionaire was close to going bankrupt. Paying out a divorce settlement would put him in the lowest financial place he’d ever been. Ivana Trump demanded more, but Trump’s banks said no.

Next: Donald Trump was in hot water with the banks. 

Donald Trump could not afford to pay Ivana Trump a settlement

US developer Donald Trump (R) walks down Fifth Avenue past a beggar after holding a news conference on November 16, 1990. He had reached a deal that will temporarily force his Taj Mahal casino into bankruptcy court. | Timothy A. Clary/AFP/Getty Images

According to The New York Times, Donald Trump reportedly asked his banks for $10 million to help pay the settlement to Ivana Trump. The banks refused. Ivana Trump had estimated her husband’s assets to be about $5 billion the previous year. With his hotels and other properties sinking, the man was hardly worth a penny.

Next: Trump eventually scraped up the divorce cash. 

Donald and Ivana Trump settled on $14 million, plus more

Trump Tower stands along 5th Avenue in Manhattan as police stand guard outside

She got an apartment at a Trump property as part of the deal. | Spencer Platt/Getty Images

Rather than risk settling for even less money, Ivana Trump decided to take Donald Trump’s $25 million offer. Donald Trump scraped up the money, and his ex-wife walked away with $14 million plus assets, The New York Times reported. She received their 45-room Greenwich, Connecticut mansion along with an apartment in the Trump Plaza. Ivana Trump was also granted use of Donald Trump’s Mar-a-Lago mansion for one month of the year.

Next: Trump also had to pay a very expensive child support. 

Ivana Trump also got $650,000 per year for the Trump children

She raised the Trump children practically on her own. | Grant Lamos IV/Getty Images

As part of the settlement, Donald Trump would have to pay $650,000 per year in child support for his children. Ivana Trump received sole custody of their three kids, Ivanka, Eric, and Donald Trump Jr. In an interview with Page Six in 2017, Ivana Trump claimed that Donald Trump “had no idea what to do” with her children. She said she’d raised them practically by herself.

Next: Finally, the divorce was over. 

The couple officially divorced in 1992

Ivana Trump was happy to move on after the divorce. | Diane Freed/Getty Images

After three years of back and forth, the divorce was finalized in 1992. In 2017, Ivana Trump reflected on the years that shook her world during one of the messiest-ever divorces between public figures. “I can only shake my head at how insane it was,” she wrote in her memoir. “I couldn’t turn on the television without hearing my name.”

Next: Trump didn’t wait long to marry Maples. 

Donald Trump wed Maples in 1993

Donald Trump and Marla Maples in 1991

Donald Trump and Marla Maples in 1991 | Timothy A. Clary/AFP/Getty Images

Donald Trump went on to marry his mistress in 1993 — the two already shared a daughter together, Tiffany, who was born two months before the wedding. The couple married at The Plaza in front of 1,100 guests. Maples wore a $2 million tiara. There were hundreds of onlookers as the man who once said he had a “marriage phobia” wed his second wife.

Next: The marriage folded in less time than the first. 

They had a messy divorce in 1999

Trump (here in 1999) was already dating as the divorce was being finalized. | Jeff Haynes/AFP/Getty Images

The marriage didn’t last too long. Maples said that Trump was attention-seeking and ego-driven and that he couldn’t be changed. She said that once she became a mother, she was less willing to put up with his behavior. According to the NY Daily News, Maples said Trump failed to provide for their five-year-old daughter, Tiffany. Trump said in a later interview with Howard Stern that he “got rid of” Maples at the perfect time, and he was very happy.

Next: Maples was very displeased with her divorce settlement. 

Maples only got $2 million in the settlement

Donald Trump and Marla Maples appear in front of t

Her divorce settlement was a much as her wedding tiara cost. | Bob Strong/AFP/Getty Images

After battling it out with Trump to try and get more money, Maples finally settled on a $2 million settlement — the same price as the tiara she wore at their wedding. The NY Daily News reported that Maples claimed she had signed the agreement under duress only two days before their wedding. She said she’d only had five days to look it over. However, after a long, public battle with Trump, she walked away with $2 million.

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