A Brief History of Donald Trump's Relationship With Playboy and Appetite for Female Nudity

Karen McDougal, a former Playmate, alleges that she had a long affair with Trump, during which he offered to pay her for sex. And Stormy Daniels, whose long-teased interview with Anderson Cooper ran on Sunday evening, said she has conclusive proof that she, too, had a fling with the then-businessman. These accusations reach back to the mid-2000s, but Trump's intertwining with Playboy and other adult publications goes back a good 30 years.

This is by necessity and incomplete history, because for all his brashness, Trump didn't exactly trumpet all of his sexual indiscretions. For example, it took until 2015 for the world to learn that he pursued a sexual relationship with Sandra Taylor, a former Penthouse Pet, in 1991. Their alleged tryst didn't last long, but Trump clearly left an impression, as she told The New York Post Trump "was great" in bed.

A year prior, Trump was featured on the cover of Playboy, next to Playmate Brandi Brandt. The cover came complete with one of those absurdly long print profiles that could never run today. It's mostly focused on business and his ostentatious lifestyle -- he hadn't gone bankrupt yet -- but it does touch briefly on his love life, at least philosophically. He refuses to talk about his marriage, likely because he was engaged in an affair with Marla Maples at that point, but does admit to enjoying the chase.

"I think any man enjoys flirtations, and if he said he didn't, he'd be lying or he'd be a politician trying to get the extra four votes," Trump said, which is ironic in retrospect. "I think everybody likes knowing he's well responded to, especially as you get into certain strata where there is an ego involved and a high level of success. It's important."

Notably, Trump was trying to get his love life into Playboy at that time, just in a very different format. When their relationship became public, Playboy offered Maples in excess of $1 million to pose nude for the magazine's centerfold. Trump reportedly tried to convince Maples to take the deal, but she refused. "I'm thankful for my body, but I didn't want to exploit it," Maples explained. "How would I ever be taken seriously?"

This was nothing new for Trump, as he had reportedly tried to pull a similar stunt with his employees before that (though it's unlikely they would have seen a million bucks). A 1991 book titled "Trump, The Greatest Show on Earth: The Deals, The Downfall, The Reinvention," alleged that Trump pitched a photo shoot that would be called "The Girls of Trump," which would feature some of his more attractive secretaries and staffers. The book says he made a series of offers, "a sliding scale of everything from full nude to breast to 'wet-lip' shots," but it never came to fruition.

Trump's desire to place women in revealing photo shoots was satisfied by the creation of Trump Models, a modeling agency that opened in 1999 and closed down last year, without much notable success during its near-two decade run.

More significantly, he owned the Miss Universe pageant for nearly 20 years, from 1996 to 2015, and was highly involved in everything from marketing to choosing which women would advance in the competitions. His tendency to walk through backstage changing rooms filled with half-naked women was well-documented, and not particularly appreciated.

The businessman was at a personal and professional low in 1997, when he was next featured in the pages of Playboy. He didn't make the cover, and the writer of the profile, Mark Bowden, later remembered just how many lies Trump told him over the course of their interviews -- everything from Michael Jackson and Lisa Marie Presley having a romantic weekend together in Mar-a-Lago, to owning a rug designed by Walt Disney. He hated the profile, but stayed friends with the magazine.

That he was so entrenched in the world of Playboy was at least in part a function of his close relationship with Hugh Hefner. Trump was a frequent guest at the Playboy Mansion over the years, partying in both private and public; he appeared at anniversary parties in 1993 and 1998 -- Holly Madison has remembered seeing him around the place -- and took contestants from "The Apprentice" there as a reward for winning competitions. Tom Arnold also told TMZ that he used to party with Trump at the Playboy Mansion, though alas, he didn't offer up any dates or salacious details.

Trump even made an appearance in a 2000 softcore porn video produced by the magazine, though whatever Stormy Daniels is promising to show the world was not ever revealed in the turn-of-the-century skin flick. There was plenty of nudity in the film, of course -- just none featuring The Donald.

The relationship between Hefner and Trump later crumbled; though the late Playboy mogul hailed Trump's rise in politics as proof that the GOP had lost the moral war it had been fighting for half a century, his son Cooper expressed regret about their association. "We don't respect the guy," Cooper told The Hollywood Reporter in 2016. "There's a personal embarrassment because Trump is somebody who has been on our cover."

But there is yet hope for the relationship: Tiffany Trump attended a Playboy party this past New Year's Eve. And as the daughter of Marla Maples, who spurned their offer all those years ago, it was an especially poignant visit.