From playboy to president: Trump's past crude sex talk collides with White House bid

Miss Estonia, Kristiina Heinmets, and Donald Trump, pose for photographs on May 09 1997 in Miami Beach. Photo / Getty Images

Over 15 years, radio shock jock Howard Stern and his buddy Donald Trump periodically carried on like towel-snapping "bros" in a locker room, rating women's tops and bottoms, debating whether oral sex is "important," and egging each other on about whether they would like to go to bed with a number of people, from Cindy Crawford to Diane Sawyer.

"You could've gotten her, right?" Stern asked Trump on-air shortly after Princess Diana's death in 1997. "You could've nailed her."

"I think I could have," Trump said.

How about singer Mariah Carey? "Would you bang her?" Stern asked. Trump replied, "I would do it without hesitation."

Trump's crude talk on-air with Stern between 1990 and 2005 was part of an image he cultivated as a Manhattan playboy who had so many women that he barely had time to sleep. He was often seen at trendy nightclubs with different women, appeared on the cover of Playboy magazine, wrote in his books about all the women chasing him and publicly boasted about his sex life.

Alison Stern and Howard Stern. Photo / Getty Images

That reputation was useful as Trump, in his 40s and 50s, built a brand designed to equate his name with success and the high life. But it is problematic as Trump, 69, the presumptive Republican presidential nominee, tries to wash away his tabloid past and fashion a more dignified persona - as a potential commander in chief and leader of the free world.

Although Trump promises to be "more presidential," his past statements have contributed to high negative ratings from women. Democrats have signaled they will make Trump's history a centerpiece of their campaign against him and other Republicans this fall.

Trump's exchanges with Stern, many of which BuzzFeed posted online earlier this year, are featured in a new ad by the Democratic candidate in the U.S. Senate race in Arkansas.

20 years ago, Trump was a younger version of Hugh Hefner

The contrast between Trump's past and present behavior underscores the extent to which he has shaped and reshaped his identity as he has moved between business, entertainment and politics. And it points to a fundamental question about his candidacy: Which version of Trump might America send to the Oval Office?

"Defining Donald Trump will be one of the real challenges of this campaign," said Ed Rollins, a veteran GOP consultant who last week began working for a pro-Trump super PAC. "Ten or 20 years ago, Trump was a rogue character . . . a younger version of Hugh Hefner. Today he is a seen as a successful businessman and a celebrity and a good father."

Trump, in an interview, played down the significance of some of his past behavior.

"I never anticipated running for office or being a politician, so I could have fun with Howard on the radio and everyone would love it. People do love it," Trump said, sitting behind his Trump Tower desk piled with magazines featuring his face on the cover. "I could say whatever I wanted when I was an entrepreneur, a business guy."

US Republican presidential candidate Donald Trump speaks in New York on May 3, 2016, following the primary in Indiana. Photo / Getty Images

Trump also said his work was so "all-consuming" that he could not have been the libidinous playboy portrayed in the media.

People may be surprised that my life is much simpler than they thought

"People may be surprised that my life is much simpler than they thought," said Trump, with a Diet Coke in a plastic cup on his desk. "And they may be surprised that my life is much less glamorous than they thought, including every story about a supermodel."

Trump said the media coverage of his personal life was "overblown."

But it is clear that Trump played a role in shaping public perceptions.

He wrote in his best-selling books that a parade of famous women wanted to date him. In his 1997 "Art of the Comeback," he wrote, "If I told the real stories of my experiences with women, often seemingly very happily married and important women, this book would be a guaranteed best-seller (which it will be anyway!)." He also wrote in that book about being "linked to dozens of other women. . . . It was incredible, being intimately associated with women I had never heard of. Women themselves - some very famous - were linking themselves to me. I guess they wanted some of the publicity. They were calling. Their agents were calling. It was a circus! It was sick!"

After his public split with his first wife, Ivana, in 1990, Trump often got more media attention for his dates than his deals. From then until 2005, when he married his third and current wife, Melania Knauss, Trump's social life was a tabloid staple. During that time, he had a second tumultuous marriage, to beauty contestant Marla Maples, who was quoted on the cover of the New York Post as saying about Trump: "Best Sex I Ever Had."

In between his marriages, a string of celebrities, including Madonna and Kim Basinger, were reported to have been chasing Trump - these women denied that, though. The rumors, even if not true, along with a string of women whom Trump showed up with at high-profile events, left the impression that he was a man about town.

Miss Puerto Rico Zuleyka Rivera Mendoza poses with Donald Trump on stage after being named Miss Universe during the Miss Universe 2006 pageant. Photo / Getty Images

All of the attention differentiated Trump from other wealthy real estate developers. And Trump reveled in it, according to several longtime associates. Those people, who spoke on the condition of anonymity, said Trump made a point of surrounding himself with young, attractive women. When he threw parties at his Mar-a-Lago estate in Palm Beach, Fla., they said, Trump got his friends at modeling agencies to send women who floated around his pool and piled into his limousine.

After he bought the Miss Universe pageant in 1996, Trump was seen by a national TV audience in a sea of contestants in bathing suits and high heels.

"There's 100 beautiful women and 10 guys. Look, how cool are we?" said Roger Stone, a political adviser who has known Trump for decades, recalling the Palm Beach parties. "I was happy to be invited. I mean it was great."

Trump's own comments focused attention on his libido, not just his skyscrapers.

When asked by Playboy magazine in 2004 about Viagra, Trump boasted: "I just have never needed it." He went on to say that what he really needed was an "anti-Viagra, something with the opposite effect."

"I'm not bragging," he bragged. "I'm just lucky."

Trump's rise as a figure in popular culture helped propel him from business into television stardom when, in 2004, he debuted in his NBC reality show, "The Apprentice." During one season of the show, Trump drove up to Hefner's mansion in a limousine and was on TV surrounded by Playboy bunnies wearing pink ears and little else.

Some of Trump's most raw language came during his appearances with Stern, when the two would critique women's looks.

The BuzzFeed list included one clip in which Trump said: "Her boob job is terrible. They look like two light posts coming out of a body." In another clip, Trump said, "A person who is very flat-chested is very hard to be a 10."

Stern had a huge national audience and made a name for himself with off-color questions, like this one, to Trump: "Is oral sex important to you? Man to man, and I've had this discussion with many men."

Trump responded, "No, it's not important to me."

Surrounded by his supporters and family, Republican presidential candidate Donald Trump addresses the media at Trump Tower following primary election results on May 3. Photo / Getty Images

In his recent interview with The Washington Post, Trump said he and Stern "had great moments" on the air, but he acknowledged he would not have said certain things had he known then that he would eventually be running for office. "Or I wouldn't have gone on the show because that is the easier way of doing it," Trump said.

Trump said Stern is a good friend, "a really good guy and a very different guy when you take the radio microphone away." Stern declined to comment.

With the Republican nomination in his grasp, Trump has projected a more familiar image for a possible president - that of a family man.

His children, particularly the older ones, are constantly with him on the campaign trail and speak out on his behalf. His daughter Ivanka, 34, an executive vice president of the Trump Organization, is the star of many ads aired across the country in which she says her father told her that she could do anything - same as her brothers - if she worked hard.

Candidate Trump recently sold the Miss Universe pageant.

'I greatly respect women'

Trump told The Post that his record of promoting women to high-level positions in his business is more relevant than any past comment.

"I greatly respect women," Trump said.

Asked whether he is obsessed by women's looks given the frequent comments he makes about them, Trump said, "Much less so than people would think."

Some who knew Trump in the 1990s say he was not an overheated Casanova. Rather, he was a workaholic aware of the value of being perceived as such.

"I never heard him speak romantically about a woman," said Trump's former attorney Jay Goldberg, who was often by his side during those years. "I heard him speak romantically about his work."

"Give him a Hershey's bar and let him watch television," Goldberg said. "I only remember him finishing the day [by] going home, not necessarily with a woman but with a bag of candy . . . not Godiva, just something from the newsstand."

Kate Bohner, co-author of "The Art of the Comeback," said, "There were times when I'd see him chatting up a bevy of gorgeous creatures, and I can see how an outsider might think he was in it to win it, so to speak. But never did I feel that it was anything other than part of his shtick to fuel the Trump brand. I saw Mr. Trump being more paternal toward women than playboy."

Peter Osnos, who edited Trump's 1987 "The Art of the Deal," said that Trump "cultivated celebrity" but that "his lifestyle was surprisingly unglamorous."

"He's quite disciplined in some ways," Osnos said. "Doesn't smoke, doesn't drink."

Trump's effort to adjust his image was apparent in the fall, when, as a candidate, he appeared again on the air with his old pal Stern.

The radio host brought up Fox News anchor Megyn Kelly. She had just asked Trump during a presidential debate about all of the negative words he used to describe women over the years, including "fat pigs," "dogs" and "slobs."

Stern seemed ready to relive the old days with his friend, baiting Trump to rate Kelly's looks.

"What is she on a scale of 1 to 10?" Stern asked.

But playboy Trump had left the room. The question, instead, was handled by candidate Trump.

"In the old days," he said, "I wouldn't have minded answering that question. Today, I will take a pass."