According to Heidi Parker, who served as West Coast Bureau Chief for Playboy magazine from 2003 until 2006, Trump called Hefner at home in 2004 and "demanded he be on the cover with the female cast of 'The Apprentice.'"
"Three of the women from the first season of 'The Apprentice' wanted to pose nude for the magazine. But Trump stepped in and said they could only do so if he was on the cover with them," Parker wrote in an op-ed for the Daily Mail. "Hef said 'Ewww.'"
Wait, once isn't enough. We all need to read that quote again: "Hef said 'Ewww.'"
Parker's details her encounters with Hefner over the years, painting him as a gentle, yet tough boss, who was obsessed with getting Britney Spears to pose for Playboy. Hefner's son, Cooper, made it clear this past August in a Hollywood Reporter interview that the family was not a fan of Trump.
"We don't respect the guy," Cooper said. "There's a personal embarrassment because Trump is somebody who has been on our cover."
But apparently Hefner didn't want Trump to know that, at least in 2004.
"Trump had been on the cover before in 1990 with model Brandi Brandt. And Donald's assistant told me it sold so well that we should be begging for him to do it again," Parker wrote. "Hef said no, and he let me take the fall on that one, telling Trump that Heidi Parker didn't like the idea. Like I had any say. I never did."
"Donald was not happy with this news. The icon let Hef know I should be fired, I learned through Hef's secretary. 'Donald thinks he's friends with Hef but they're not friends and there is no way Hef wants Trump on the cover again!' Hef's secretary told me," Parker went on in her column. "I was shocked Trump wanted me fired and even more shocked Hef pretended to be his friend but really didn't like him at all."
Trump proudly signed copies of his 1990 cover on the campaign trail and boasted to a Washington Post reporter, "I was one of the few men in the history of Playboy to be on the cover."
Cooper, who is now in charge at Playboy, made it clear last month that he does not see eye to eye with Trump or Republicans on a number of issues.
"I'm a liberal, and I have a real issue with the conservative side feeling like they own the military," he told THR, and teased that Playboy will continue to challenge the establishment, much like it did when his dad founded it in 1953.
"Yes, there are lifestyle components to Playboy, but it's really a philosophy about freedom. And right now, as history is repeating itself in real time, I want Playboy to be central to that conversation."