Donald Trump & Playboy: 5 Fast Facts You Need to Know

Donald Trump Playboy, Donald Trump Hugh Hefner

Getty Playmate Victoria Silvstedt, Donald Trump and his wife Melania at the Playboy 50th anniversary part in 2003.

At the height of his days as a celebrity, President Donald Trump made no effort to hide his relationship with Playboy Magazine, which went all the way to back to a 1990 cover story. Trump still has a framed copy on a wall in Trump Tower, as a tweet posted by Jerry Fallwell in June 2016.

During the campaign, Trump’s appearances in soft-core, pornographic Playboy videos have surfaced. In June 2016, Playboy founder Hugh Hefner even praised Republicans for voting for Trump during the primaries, suggesting that it highlighted a “sexual revolution in the Republican Party.”

Trump’s treatment of women was in the spotlight continuously throughout the 2016 election cycle and reached new heights with the release of a 2005 tape in which he recounted a failed sexual encounter with then-Access Hollywood anchor Nancy O’Dell while they were both married to other people.

Here is a look at Trump’s relationship with Playboy Magazine.

1. Trump Said in his 1990 Playboy Interview That He Would do Better in a Presidential Election as a Democrat

Donald Trump, Donald Trump Playboy cover, Donald Trump North Carolina

Donald Trump with his 1990 Playboy Magazine issue at a Raleigh campaign stop in July 2016. (Getty)

Among the many interesting tidbits in Trump’s 1990 interview with Playboy – which can be read in its entirety here – is a discussion on politics. Writer Glenn Plaskin asked Trump which political party he was more comfortable with. He replied:

Well, if I ever ran for office, I’d do better as a Democrat than as a Republican–and that’s not because I’d be more liberal, because I’m conservative. But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.

Plaskin then asked Trump what his first move would be as president. He replied:

Many things. A toughness of attitude would prevail. I’d throw a tax on every Mercedes-Benz rolling into this country and on all Japanese products, and we’d have wonderful allies again.

Trump went on to say that he would always support then-President George H.W. Bush, but even at then, Trump complained about America getting soft.

“I think if this country gets any kinder or gentler, it’s literally going to cease to exist,” Trump said. “I think if we had people from the business community–the Carl Icahns, the Ross Perots–negotiating some of our foreign policy, we’d have respect around the world.”

Later in the interview, Trump Trump said he is “one hundred percent sure” that he doesn’t want to be president. But, he added, “I’d change my mind only if I saw this country continue to go down the tubes.”

2. Trump’s 1997 Interview With Playboy Declared His ‘Comeback of a Lifetime’

Donald Trump 1996, Donald Trump 90s, Donald Trump smile, Donald Trump Playboy

Donald Trump in 1996. (Getty)

In 1991, Trump and his first wife, Ivana, got a divorce. He married Marla Maples in 1993, although they divorced by 1997. In 1996, while still married to Maples, Mark Bowden was assigned to do a new story and interview with Trump for Playboy. Titled “The Art of the Donald,” it was published in the May 1997 and declared, “The Trumpster Stages the Comeback of a Lifetime.” You can read the entire piece here.

This 1996 interview also includes quotes from Maples. “I like her with a little more meat on her bones than this,” Trump is quoted as saying, with his arms around Maples. “She plumped up a little when she had Tiffany. That was nice.”

Trump then tells her she “looked better” when she was pregnant. Maples is quoted as telling him, “You just like girls to look like the ones in Playboy. Why don’t you buy it? Well, you bought the Miss Universe pageant. Playboy would be right up your alley.”

In December 2015, Bowden wrote about the experience of writing that Playboy piece for Vanity Fair. Bowden wrote that while he was writing Black Hawk Down, he got a call from Trump’s assistant, who told him Trump was “too livid to speak” after reading the published Playboy piece. Bowden wrote:

His latest outrageous edict on banning all Muslims from entering the country comes as no surprise to me based on the man I met nearly 20 years ago. He has no coherent political philosophy, so comparisons with Fascist leaders miss the mark. He just reacts. Trump lives in a fantasy of perfection, with himself as its animating force.

3. Trump Appeared in at Least 3 Playboy Pornographic Videos

Donald Trump 1990s, Donald Trump Playboy, Donald Trump Marla Maples

Donald Trump with Marla Maples in 1991. (Getty)

On September 30, BuzzFeed obtained footage from a 2000 softcore pornographic Playboy video called Playboy Video Centerfold that featured two Playmates traveling the country. When they arrive in New York, they meet Trump, who is seen pouring champagne on a Playboy-branded limousine. Although the VHS does include nudity, Trump is not seen in those scenes.

On October 6, CNN obtained footage from a 1994 Playboy Centerfold VHS, in which Trump is seen interviewing a model who wants to appear on Playboy’s 40th anniversary cover. Again, Trump is not in any of the scenes that include nudity.

“I thought he was thoughtful. I thought he was respectful. I had a very good time,” Bridget Marks, a model Trump interviews in the video, told CNN. “He has remembered my name and been very nice to me and my family whenever I’ve seen him.”

CNN found that Trump appeared in a 2001 Playboy video on a fashion show, in which he is also not in scenes with nudity. In that video, he is seen with his current wife, Melania.

Donald Trump at the Playboy MansionFrom season 6, episode 2 of "The Apprentice." Donald Trump rewards a team of contestants with a trip to the Playboy mansion. Read more:

As seen in the above video, Trump also took The Apprentice contestants to the Playboy Mansion during season six. Sura Yalamanchili was a contestant that season and wrote about her experiences at the Playboy Mansion for Politico in April. She wrote:

Toward the end of the evening, I found myself in a small circle, conversing with Trump, Hefner and another contestant. With a wry smile, Trump looked at Hefner and said, “It’s hard for me to tell which of these girls are yours, and which ones are mine.” The women on my team were well-credentialed business executives, people Trump had supposedly hand-picked for their skills. 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.

4. Hugh Hefner Said Trump’s Wins in the Primaries Were Signs of a ‘Sexual Revolution in the Republican Party’

Donald Trump, Donald Trump The Apprentice, Donald Trump Playboy

Donald Trump in 2012. (Getty)

In June 2016, Hefner wrote a op-ed called “The Conservative Sex Movement,” in which he suggested that the failure of Ted Cruz and the success of Trump was a “sexual revolution in the Republican Party.”

While the op-ed doesn’t really endorse Trump, it does suggest that his success showed the party understanding how social conservatism did not help it win the White House in 2008 or 2012. He also warned that there are Republicans who are still seeking to limit abortion. Hefner’s piece was published before Trump picked Mike Pence, who is anti-abortion, as his running mate.

“We won the sexual revolution; it has just taken Republicans 50 years to admit defeat. Now it’s time for them to exit our bedrooms and close the door behind them forever,” Hefner wrote.

5. Hefner’s Son Cooper Urged Millennials Not to Vote for Trump, Comparing Him to George Wallace

Hugh Hefner son, Cooper Hefner, Donald Trump Playboy

Hugh and Cooper Hefner. (Getty)

Cooper Hefner, Hugh Hefner’s 25-year-old son, wrote in a March Hop.Media post that Trump is a “family friend.” However, that didn’t stop him from blasting the candidate. Cooper is hoping that millennials will not vote for Trump and compared him to controversial Alabama Governor George Wallace who ran for president in 1968. Cooper wrote:

Trump is an individual who has openly advocated banning and deporting Muslim Americans and legal immigrants, taking a massive step backwards towards the political and social philosophies inherited from eras of slavery and gender inequality, like the Japanese-American prison camps of World War II, women not having the right to vote, and segregation between blacks and whites. It seems that is Trump’s idea of making America great again.

Days after Cooper’s piece was published, he went on CNBC to explain his position.

“He sort of is rewriting the playbook for how every individual has gone about running their campaign. Most importantly, I think most of his policies are backed and supported by racist notions,” Cooper said.

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