Donald Trump's Relationship With Hugh Hefner Took A Turn Nobody Was Expecting

October 13, 2024

Highlights

Hugh Hefner's son dishes on the mystery around Donald Trump's friendship fallout.
Past Playmate comments on Trump's respectful demeanor during Playboy Mansion visits.
Trump and Playboy have a history of alliance that took a turn with possible political clashes.

Throughout the '90s and into the 2000s, it seemed like Donald Trump and Hugh Hefner were not only on good terms, but actually close with one another. Hefner even endorsed Donald Trump's political run at the start. However, things soured, and Cooper Hefner hinted at the moment his dad stopped being friends with Donald.

In the following, we're going to take a closer look at what went down between the two, and the history shared between Playboy and Donald Trump. We'll also reveal what Trump was like during his appearances at the Playboy Mansion over the years. Trump made several appearances, and former Playmate Holly Madison commented on what he was really like behind the scenes.

Let's take a closer look.

2:07

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High Hefner and Playboy made Taylor Swift a tempting offer back in 2016, completely changing the direction of its magazine.

Hugh Hefner's Son Cooper Said His Father's Relationship With Trump Suddenly Changed Over Different Philosophies

There was a lot of confusion over Hefner's changing relationship with Donald Trump. The two had a lengthy history together, which seemed to be positive, especially given that Donald was the first male on the cover of Playboy in 1990. Even when Trump was running for President, Hugh Hefner showed lots of optimism.

Hefner said at the time, "Voters nominated Donald Trump, a thrice-married New York entrepreneur who once owned the Miss USA pageant, over Cruz, the son of a pastor," Hefner wrote. "It's a sign of the massive changes in the 'family values party' and proof of…a sexual revolution in the Republican Party."

However, it seems like things changed after Hefner's son, Cooper, stated that his dad was embarrassed over Trump's magazine cover.

"We don't respect the guy. There's a personal embarrassment because Trump is somebody who has been on our cover."

There wasn't an exact reason as to why, but rumors suggest Trump hiring Mike Pence as his Vice-President might've had something to do with it. Hefner was a supporter of LGBT rights, while Pence opposed gay marriage. Trump also put a ban on transgender joining the military, which also received a lot of hate.

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Trump hasn't said anything in return to Cooper's comments - Trump also chose to keep quiet following Hefner's passing.

Donald Trump Had A Lengthy History With Playboy That Was Amicable For Years

Trump's history with Playboy started back in March of 1990 when he appeared on the cover. Even back then, Trump was talking about the country, and the direction it was headed in.

“I hate seeing this country go to hell,” he said. “We’re laughed at by the rest of the world.”

According to People, Trump was even spotted at Playboy's 50th anniversary party in 2003 alongside Melania Trump.

People wrote, "Trump attended Playboy‘s 50th anniversary party in 2003, where he was accompanied by his future wife, Melania Trump, then Melania Knauss. The Trumps were photographed with Hefner and his then-girlfriend and co-star on The Girls Next Door, Holly Madison, as well as Playboy model Victoria Silvstedt."

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Trump made multiple appearances at the Playboy Mansion. Surya Yalamanchili discussed what it was like going to the Playboy party with Trump.

She said about one of his interactions with Hefner, “The women on my team were well-credentialed business executives, people Trump had supposedly hand-picked for their skills,” Yalamanchili wrote. “In that moment, the only real difference to Trump between them and the scantily clad Playmates who were there for his entertainment was that some of the women were ‘his,’ and some weren’t.”

He allegedly said, “It’s hard for me to tell which of these girls are yours, and which ones are mine.”

There weren't any stories of Trump being disrespectful and, in fact, it was the opposite according to other playmates.

Holly Madison Said Donald Trump Was Respectful To Everyone During His Time At The Mansion

Playboy Playmate Holly Madison recalled her time with Donald Trump. Given her history with him, she found it surreal that he was President of the United States.

Madison revealed, "It's kind of surreal seeing Donald Trump run for president because I used to see him at parties sometimes and run into him," she said. "I was a judge at his Miss USA pageant when he used to own it, so it's definitely kind of surreal and weird."

Madison continued on, stating that Donald always treated her with respect during their random encounters at the mansion.

"I met Donald Trump a few times, but I don't know him well or anything. He was always polite and really nice."

As for Madison's relationship with Hefner, it was completely broken. Madison defended the fact that she didn't mourn his death.

“When he passed away, everybody expected me to have some big reaction or post about it on social media, and it just felt weird. I didn't have any emotional attachment to him anymore in any way."

It certainly was a troubling time for Madison alongside Hefner.

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