Trump tries to move from playboy to president

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.

Trump's crude talk with Stern between 1990 and 2005 was part of an image he cultivated as a Manhattan playboy who had so many women 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.

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 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.

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 among 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 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. "I could say whatever I wanted when I was an entrepreneur, a business guy."

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," he said.

Media coverage of his personal life was "overblown," he said. 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!)."

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.

Trump reveled in the attention, 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. Candidate Trump sold the pageant.

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, 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."

In his recent interview with the Washington Post, Trump said he and Stern "had great moments" on air, but he acknowledged he would not have said certain things or gone on the show had he known then that he would eventually run for office.

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 on his behalf.

Kate Bohner, coauthor 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."