Playboy founder Hugh Hefner, who died on September 27 at age 91, might have been best known for his role in the sexual revolution, but he was also a voice in politics. But future President Donald Trump wasn’t attracted to the Playboy world because of politics. As a celebrity, long before even The Apprentice, Trump found himself in the Playboy orbit and even landed on the cover of the magazine in 1990. During the 2016 presidential campaign, video of Trump in softcore Playboy tapes surfaced.
“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” Hefner’s son, Cooper Hefner, now Chief Creative Officer of Playboy Enterprises, said in a statement. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston and all of us at Playboy Enterprises.”
Here’s a look at Trump’s relationship with Playboy and what Hugh Hefner thought of him.
1. Cooper Hefner Said They Regretted Putting Trump on the Cover, Adding, ‘We Don’t Respect the Guy’
A month before his father’s death, Cooper did an extensive interview with The Hollywood Reporter, in which he said it was remarkable to see the U.S. revert back to the cultural conservatism that his father fought against. He added that the company is now embarrassed to have published an issue that included Trump on the cover.
“We don’t respect the guy,” Cooper told THR. “There’s a personal embarrassment because Trump is somebody who has been on our cover.”
The magazine was left in good hands, and Cooper hopes that the Playboy of the future can be just as important as it was in the 1950s.
“Yes, there are lifestyle components to Playboy, but it’s really a philosophy about freedom,” Cooper told THR. “And right now, as history is repeating itself in real time, I want Playboy to be central to that conversation.”
While Playboy might be embarrassed by the cover, Trump is not. The cover infamously appeared in the background of a picture Trump took at his office with Evangelist Jerry Falwell Jr. during the presidential campaign.
2. Hefner Hoped Trump’s Presidential Nomination Was Proof of a ‘Sexual Revolution in the Republican Party’
Hefner was hopeful that the nomination of Trump was a sign that Republicans were turning their backs on social conservatism. In June 2016, he wrote an op-ed called “The Conservative Sex Movement,” in which he wrote that Trump’s victory over Texas Senator Ted Cruz proved that there was a “sexual revolution in the Republican Party.”
“After losing two presidential elections, core conservatives realize the time has come for the party to stop pandering to America’s fanatical religious minority and give up a losing war to suppress our sexual rights,” Hefner wrote.
But Hefner didn’t endorse Trump and he noted that Republicans were still waging a war against socially progressive policies. After all, the op-ed was published after Indiana Governor Mike Pence was picked to be Trump’s running-mate. Pence is strongly anti-abortion and wanted to strip Planned Parenthood of federal funding.
“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.
3. Trump Told Playboy in 1990 That He Thought He’d Be a Better Presidential Candidate as a Democrat
Trump’s 1990 Playboy interview with Glenn Plaskin is a fascinating look at how Trump viewed the world at the time. In it, he said he was “conservative” and even predicted that the “working guy would elect me” if he ran for president. But he said he would do better as a Democrat.
“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,” Trump told Plaskin. “But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.”
But other than his party affiliation, the interview reveals that even at that time, he complained about America getting soft. He also said “a toughness of attitude would prevail” if he was elected President and he’d put a tax on “every Mercedes-Benz rolling into this country and on all Japanese products.”
Trump even suggested that if members of the business community were setting foreign policy, the U.S. would be more respected. Twenty-six years later, Trump named former ExxonMobil CEO Rex Tillerson Secretary of State.
Trump was profiled by Playboy again in the May 1997 issue, under the headline “The Art of the Donald: The Trumpster Stages the Comeback of a Lifetime.” The author of that piece, Mark Bowden, Wrote about the experience for Vanity Fair in December 2015.
“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,” Bowden wrote. “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.”
4. Trump Took ‘The Apprentice’ Candidates to The Playboy Mansion to Meet Hefner in 2006
One of the stories that resurfaced during the presidential campaign was Trump’s visit to The Playboy Mansion during the 2006 season of The Apprentice to have the contestants meet Hefner. The visit was featured in the second episode of the season as a “reward.”
In April 2016, one of the contestants, Surya Yalamanchili, Wrote about his experiences on the show for Politico. The Playboy Mansion trip was particularly uncomfortable, he wrote. At one point, Trump told Hefner, “It’s hard for me to tell which of these girls are yours, and which ones are mine,” Yalamanchili wrote, even though the women on The Apprentice were experienced business executives.
“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.”
In October 2016, another contestant, Jenn Hoffman, wrote about her experience at the mansion for Esquire. “Off camera but within our earshot, I heard Trump say that he had wanted to reward the other guys by giving them a shot at a potential hook-up,” Hoffman wrote.
Hoffman wrote that she was a little excited about a trip to “this iconic, last bastion of benevolent sexism, the Disney World of misogyny.” But she wondered if this was really appropriate for part of a job interview. She considered skipping, but that wasn’t allowed. “Stay home and you risked that most fiendish of reality-TV punishments—an unflattering edit,” she wrote.
Hoffman wrote that Trump even compared her and fellow contestant Kristine Lefebvre’s breasts with the Playboy bunnies’. “Ours were beautiful, he appraised, maybe even better than the bunnies’; staring at our chests, he confidently declared that we didn’t even need ‘the enhancements,'” she wrote. “I wasn’t offended by his observations, I was more amused by how he’s not the breast expert he thinks he is.”
Lefebvre later appeared on the cover of Playboy in June 2007.
5. Hefner Didn’t Make Political Donations to Trump or Clinton During the 2016 Campaign, but Celebrated Obama’s Re-Election in 2012
In 2011, Hefner tweeted that he was a registered Independent at the time. His parents were registered Republicans and he was registered as a Democrat previously. But when President Barack Obama was re-elected, he celebrated at the Playboy Mansion.
“While I was playing dominoes with the girls, we got the news that Obama had been re-elected. We’re celebrating at the Mansion,” he wrote.
According to Open Secrets, Hefner didn’t make any political contributions during the Trump or Hillary Clinton 2016 campaigns. In February 2015, he did donate to California Democratic Rep. Loretta Sanchez. A year later, he donated to the Democratic PAC Leading Orange County PAC.
In 2007, Hefner donated to Obama and Clinton’s primary campaigns and he donated to 2004 Democratic candidate John Kerry. Since at least 1989, Hefner donated exclusively to Democratic candidates.
Hefner was considered a libertarian, fighting for free speech and against censorship. In 2006, Hefner told ABC News that he was disappointed to see President George W. Bush, a Republican, make decisions based on religion.
“I would say there are a lot of things about the current administration that are surprising. That religion and religious values would play such a big part in decision making on matters relating to science, relating to birth control, relating to a great many things, that’s surprising,” Hefner said. He was 80 at the time.