But those were Trump's good old days, an era of clubs and models, long before he launched a bid for the US presidency and found himself needing to squash the lewd, party boy stories he once boasted about.
Cue David Pecker, the former publishing executive whose titles included the National Enquirer, and who on Tuesday in a Manhattan courtroom laid out the "catch and kill" strategy he carried out in a bid to support Trump's 2016 presidential campaign.
In a then-secret meeting in August 2015, Trump and his former personal lawyer Michael Cohen met with Pecker to ask how he and his publications could "help the campaign," the 72-year-old witness testified.
Speaking nonchalantly to the packed courtroom, Pecker, who will continue his testimony in the high-profile trial Thursday, recalled saying: "I would run or publish positive stories about Mr. Trump, and I would publish negative stories about his opponents."
I said that I would also be the eyes and ears" in service of the campaign, he added.
Under questioning from prosecutors, Pecker explained to jurors how along with pushing positive stories in his magazines, he would alert Cohen to any potentially damaging sources on the move.
In particular, the smooth-talking tabloid man said he thought "there would be a lot of women" who would be trying to sell stories about Trump, because the then-candidate "was well-known as the most eligible bachelor," despite having married his third wife, Melania, in 2005.
Trump "dated the most beautiful women," Pecker explained, "and it was clear that, based on my past experience, that when someone is running for a public office like this, it is very common for these women to call up a magazine like the National Enquirer to try to sell their stories."