Summary

  • Donald Trump discussed prenup strategy with Howard Stern, emphasizing the importance of lawyers in negotiations.
  • Trump shared an anecdote about the necessity of prenups, highlighting a friend's costly divorce mistake.
  • Melania Trump renegotiated her prenup multiple times, focusing on securing assets for their son and herself.

Years before Donald Trump became a political powerhouse, he was best known for his media appearances. During those days in which Trump was still regularly making cameo appearances in movies, he was a regular guest on Howard Stern's radio show.

During Stern and Trump's many interviews, the business leader said many explosive things. A memorable example of that is when he threatened to steal a writer's future girlfriends during a Stern interview. Another one of the most interesting admissions Trump made to Stern focused on the prenup that he had with Melania Trump.

Donald Trump Told Howard Stern How He Could Be Ruined If He Didn't Get A Prenup With Melania Trump

In 2004, Donald Trump made one of his appearances on The Howard Stern Show. Partway through their interview, Stern asked Trump about what kind of prenup he was going to have with Melania Trump. Without missing a beat, Trump told Stern about how he would negotiate a prenup before marrying Melania Trump the following year.

Donald Trump and Howard Stern's relationship
A photo of Donald Trump in a suit, with a shot of Howard Stern.
via Instar

After joking around with Stern a little bit on the topic, Trump explained some of his mindset on how to get a proper prenup. Most notably, Trump explained why he believed that Melania Trump would have to get a lawyer during the process of working out their agreement.

How long did Donald Trump's marriages last, according to Who's Dated Who?

Wife's Name:

When They Got Married:

Current Status:

Ivana Trump

April 9th, 1977

Divorce Finalized December 1990

Marla Maples

December 19th, 1993

Divorce Finalized in June 1999

Melania Trump

January 22nd, 2005

Still Married

"You have to have a lawyer. If she doesn't have a lawyer, which, of course, is a disaster because all of a sudden she'll show up with this killer. But if she doesn't have a lawyer, you know, it doesn't hold up."

Trump then went on to say something pretty surprising for him. After Stern asked how much money he would give Melania in a divorce for any kids they might have, Trump replied he'd give whatever she asked for.

"I'll give them whatever they want."

As their conversation continued, Trump revealed that at that point he hadn't begun negotiating a prenup with Melania Trump. However, when Stern asked Trump if he would head to the hills if Melania Trump asked for too much, he had an interesting response.

Instead of directly answering Stern's question, Trump told an anecdote about a friend of his as a cautionary tale. Based on this story, Trump made it very clear that he believed that it would be foolish of him to get married without a prenup.

Donald Trump Publicly Praised Howard Stern Years Before feud
Donald Trump and Howard Stern friendship turned into feud 
Via: Commons Licences/Deposit Photos

"I have a friend who's a total brutal killer, all right, he just kills everyone. He's a very rich guy and he's had a couple of horrible marriages. So now, he meets a new woman and he tells me, 'Donald, this is the one.' Now his last one ripped him off for about fify."

Trump continued, "You know, she was married to him for two years, she made him dinner every once in a while, and then she gets fifty million dollars. This is two years. So now, he calls me, he said, 'Donald, I've met the one.' Course, he's told me this now four times."

"And so, I said, 'You're gonna get a prenup right?'" Trump continued, "He said, 'Don, honestly I don't need it. This is the one. Now here's a guy who's a genius businessman but he's a schmuck. So what happened Robin is he married her two years ago, and about a week and a half ago, he told me, 'That son of a b***h.' It's over already so I said, 'By the way, tell me yes. Tell me you had a prenup.' He said, 'I don't. I have to go through it again.'"

Based on that story, there is no doubt that Trump believed he absolutely had to get a prenup before marrying Melania Trump. However, earlier in the interview, Trump admitted that negotiating a prenup is harder than business deals.

"I have friends who are very smart, killer people that people are afraid to even deal with them. And yet a wife, five foot two, a hundred pounds destroys them... Well, it s a very tough thing. Actually, you know, doing business deals is sort of natural and easy as far as I'm concerned. Doing prenups is a whole different deal."

Donald Trump Has Thrown Some Notorious Parties At Mar-A-Lago Despite The Fact That He Doesn't Drink
Donald trump before and after young and old 
Via: TheThings

Trump also went on to explain to jokingly explain to Stern how awkward it is to even start a conversation about getting a prenup.

In 1991, The New York Times reported that Ivana Trump got a lot from Donald Trump in their divorce. Some examples of that include a $14 million Connecticut mansion, a Trump Plaza apartment, and $650,000 annually in child support. The New York Times also reported that the settlement was close to what Donald Trump agreed to pay in the prenup he had with Ivana Trump.

"You're in love with someone. You go up to her, you tell her how in love you are. You know, in the case of Melania, 'I love you very much. You're the most beautiful woman I've ever seen and we're going to be together forever. But, just in case it doesn't work out, would you please immediately sign this.'"

Melania Trump Reportedly Renegotiated Her Prenup Years Into Her Marriage To Donald Trump

In September 2023, Page Six published an article claiming that Melania Trump had negotiated a new postnup with Donald Trump. Also, one of the two inside sources the publication spoke to stated that this wasn't the first time Melania Trump negotiated a new postnup.

“This is at least the third time Melania has renegotiated the terms of her marital agreement.”

Page Six made sure to clarify that Melania Trump didn't work out a new deal with Donald Trump because she plans to leave him. Instead, the article quoted an inside source who claimed that Melania Trump was most concerned with ensuring more money for her son.

“Melania is most concerned about maintaining and increasing a substantial trust for their son, Barron."

Does Barron Trump Have A Loving Relationship With His Father, Donald Trump_
Former president Donald Trump, Melania Trump, and son Barron 
Via: TheThings

That said, Page Six reported that the new agreement also provided Melania Trump with more if her marriage to Donald Trump ended. Specifically, the article claimed Melania Trump was entitled to more money and property.

Who is Donald Trump and Melania Trump's son, according to People?

  • Named Barron William Trump
  • Born on March 20, 2006
  • 17 years old as of February 2024

According to Page Six's sources, the renegotiated agreement was motivated by Donald Trump's various legal woes. According to the source, Melania Trump wanted to have a deal in place that can't be changed due to any civil losses Donald Trump may suffer.