Donald Trump’s Past: The Media Examines His Playboy Lifestyle & Howard Stern Interviews

Donald Trump was on the cover of Playboy in 1990 alongside model Bradi Brant. A supporter of the GOP presumptive presidential candidate had Trump autograph a copy of the magazine at a rally in Nebraska recently, which the real estate mogul and reality TV star did with a smile. The image serves as a friendly reminder that Donald has a very un-presidential past, one that the media loves to examine. From the Playboy cover to his crude sex talks with Howard Stern, it isn’t difficult to paint Donald Trump as a sexist and a misogynist.

The Hillary Clinton campaign must be happy that the media has another candidate’s past to dissect for a while. News outlets from CNN to FOX News spent countless hours providing menial updates on Hillary’s e-mail scandal. The media has turned its attention to the days when Trump would say things like suggesting he could have had sex with Princess Diana, a remark he on Howard Stern’s show not long after Diana’s tragic passing.

Is Donald Trump’s playboy past going to cost him the election? Will his interviews with Howard Stern turn some Republicans to Team Hillary? Regardless of the impact of this relatively minor setback — or, if the brief history of this campaign has taught us anything, a potential boost in the polls — could Donald Trump really become President of the United States of America?

Even if the media wanted to try to hurt the Trump campaign by replaying footage of him saying that he’d “bang” Mariah Carey and “would do it without hesitation,” there’s no reason to believe that it could do any serious damage.


Donald Trump said he wanted to build a giant wall to keep out the Mexicans, and his momentum grew.

Trump said we should ban all Muslims from entering the United States, and his momentum grew.

Donald said it was gross that Hillary Clinton had to urinate, and his momentum grew.

Why, then, would his comments about his treatment of women in the late 90s cause any alarm for the Trump campaign? Donald made up for his Mexican wall comments by posting an image of his taco bowl lunch on Cinco de Mayo with a caption that included, “I love Hispanics!” It will be interesting to see which Donald poses next to when he makes up for this with a caption that reads, “I love women’s equality!”

“You said that women like being treated badly. There’s something to that. It’s sick, isn’t it?”


According to the cumulative numbers of the most recent poll data at Real Clear Politics, Clinton is 6.4 points ahead of Trump. Of course, many of the Bernie Sanders supporters aren’t thrilled about supporting Hillary Clinton. It’s possible that a Trump-Clinton election could result in many of the Sanders supporters not voting at all. On the Republican side of things, talk of a third-party Conservative alternative could destroy any possibility other than Hillary Clinton unless the Trump Campaign somehow implodes before November.


So while Clinton will continue to get questions about Benghazi and her misuse of a private e-mail account, Donald Trump will be given the opportunity to explain how the man he was in the 90s is ready to be President today. The highly-cited interview with Howard Stern happened nearly two decades ago. More recently, Trump showed his close association with Hugh Hefner and the playboy lifestyle when an episode of The Apprentice was taped at the Playboy Mansion.

Now running uncontested, there’s no reason to believe Donald Trump won’t be the Republican Party’s candidate for POTUS in 2016. Barring a huge upset from the Sanders campaign followed by the Democratic Party’s version of a “contested convention,” the Clinton-Trump showdown for November appears inevitable.

Jon Stewart absolutely skewers Hillary Clinton here. The media quoted him on Trump and left this out.


— Shaun King (@ShaunKing) May 10, 2016

While this by no means should have any long-term ill effects on the Trump campaign, it could prove for an interesting series of questions at any of the number of debates the American public will be subjected to as Hillary Clinton battles Donald Trump for the office of President of the United States of America.

[Photo by Peter Kramer/Getty Images]