Donald Trump has never been a stranger to controversy. In fact, it seems to follow him wherever he goes. From wild parties at the Playboy mansion with Hugh Hefner to his cameo in an erotic film, Donald Trump's history with Playboy and its late founder is long and turbulent. It comes as no surprise that the man who mainstreamed the objectification of women in the mainstream media has actually featured on the cover of Playboy. But did you know that Hugh Hefner didn't really like Trump's cover on the magazine after all?
6 Trump Featured On The Playboy Cover In 1990
Trump was featured on the racy Playboy magazine's cover in 1990 and he even featured it in his New York office for a number of years next to awards from religious groups and clippings from other magazines of a less explicit nature. In the famous Playboy cover, Trump is wearing tuxedo pants, a white shirt, a cummerbund and a bow tie. But Playmate Brandi Brandt is only covered by his jacket and nothing else.
5 Trump Even Mentioned The Cover During His Presidential Election Campaign
It was no secret that the former president of the United States was extremely proud of the cover and his extensive interview inside the March 1990 edition of Playboy magazine. He boasted: "I was one of the few men in the history of Playboy to be on the cover" to a reporter taking a tour of his office during the 2016 presidential campaign. Trump embraced his association with the explicit magazine and was even said to have autographed copies of the magazine during campaign stops.
4 Trump and Hefner Were Actually Close Friends
Before their relationship soured, Donald Trump and Hugh Hefner were actually close friends with one another. In 1993, Playboy magazine invited Trump to be a guest photographer and interviewer in a nationwide Playmate search. Seven years later, Trump featured in an explicit Playboy video, which featured a number of nude women in sexual positions. In 2006, Trump even invited Hefner onto his TV show, The Apprentice to speak about the origins of the Playboy brand and give the candidates business advice. Hefner even threw a pool party for the contestants on the show with dozens of Playmates, including Karen McDougal who was named Playmate of the Year in 1998.
3 Hefner's Regrets
Hugh Hefner was hopeful that Donald Trump's presidential nomination was a sign that Republicans were moving past social conservatism, but this wasn't the case which is what fundamentally led to Hefner ending his long-standing friendship with the former president. According to Newsweek, Hefner actually wrote a piece for Playboy titled 'The Conservative Sex Movement' which was swiftly deleted from the Playboy website. In the essay, Hefner spoke of Trump's triumph over the likes of Ted Cruz in the 2016 presidential primaries as “proof of a sexual revolution in the Republican Party,” whose “voters nominated Donald Trump, a thrice-married New York entrepreneur who once owned the Miss USA pageant, over Cruz, the son of a pastor. It’s a sign of the massive changes in the ‘family values party.'”
But, Hefner's high regard for Trump soon soured as, during his presidential campaign, Trump pitched himself as a defender of the values of conservative Christians who were, interestingly, the very same people Hefner regarded as his enemies. Not only that, but Trump also appointed a social conservative who was an opponent of gay marriage, Mike Pence, as his vice president. Trump's August ban on transgender people serving in the military was definitely a cause of the relationship souring, because Hefner was a lifelong supporter of LGBT rights. In an article titled 'Donald is a Family Friend and He's Full of S***', Hugh Hefner's son depicts Donald Trump as an egotistical psychopath who would reiterate racist ideologies to satisfy his own ego.
2 Hugh Hefner Did Not Like Trump Interfering With His Creative Decisions
Former Playboy editor, Heidi Parker suggested that Hefner and Trump's dislike for one another went back as far as 2004. In 2017, Parker wrote that Trump wanted female cast members of The Celebrity Apprentice to pose on the cover of Playboy with him, to which Hefner responded "Ewww". He declined Trump's suggestion and told Parker that he didn't like the idea. Trump subsequently demanded that Parker be fired. Parker wrote: "I was shocked Trump wanted me fired and even more shocked Hef pretended to be his friend but really didn't like him at all".
1 What does Cooper Hefner have to do with it?
Cooper Hefner, the youngest son of Hugh and chief creative officer of Playboy Enterprises was not shy of voicing his disdain for Trump. In 2016, father and son Hugh and Cooper Hefner attacked 'family friend' Donald Trump for his 'backwards politics' according to the Daily Mail. They compared him to George Wallace, who was the Governor of Alabama at the time who tried to maintain segregation in schools. Cooper Hefner told The Hollywood Reporter: “We don’t respect the guy. There’s a personal embarrassment because Trump is somebody who has been on our cover.” Cooper Hefner also tweeted out that, "If the 1990 team at Playboy would have known Trump's platform than the President would have never found his way onto our cover."
"Yes, there are lifestyle components to Playboy, but it's really a philosophy about freedom. And right now, as history is repeating itself in real-time, I want Playboy to be central to that conversation." Cooper was also vocal about the fact that he didn't like the former president's populist politics. He compared his leadership to Eisenhower's conservative style in the fifties, during which thousands of Americans were interrogated over alleged links to communism.