Donald Trump appeared on the cover of Playboy in 1990.
Donald Trump appeared on the cover of Playboy in 1990.
The racy Playboy magazine cover featuring the circa-1990 version of Donald Trump graced the billionaire's New York office for years - right next to awards from religious groups and clippings from other magazines that didn't feature naked pictorials.
The cover and the extensive interview inside the March 1990 edition werea feather in Trump's cap, placing him in elite company with other political and entertainment luminaries spotlighted by the magazine.
In the famous Playboy cover photo, Trump is wearing tuxedo pants, a cummerbund and a bow tie.
But Playmate Brandi Brandt has donned his jacket - and nothing else.
"I was one of the few men in the history of Playboy to be on the cover," he boasted to a Washington Post reporter taking a tour of his office during the 2016 presidential campaign.
Trump embraced the association: During his bid for the presidency, he was known to autograph copies of the magazine, offering a quick scrawl during campaign stops.
Trump continued his relationship with Playboy over the years.
In 1993, the magazine invited him to be a guest photographer and interviewer in a nationwide Playmate search. Seven years later, Trump made a cameo in an explicit Playboy video, which featured nude women in sexual positions.
Trump also seemed to appreciate the magazine's founder, Hugh Hefner, a self-made man who built an incomparable personal brand.
During his bid for the presidency, Trump was known to autograph copies of the magazine.
In 2006, Trump even invited Hefner onto The Apprentice to tell Playboy's origin story and to dole out business advice.
But near the end of Hefner's life, as Trump transformed from businessman to candidate to commander in chief, the admiration was apparently far from mutual.
A month before Hefner died, one of his sons, Cooper, summed up their opinion of Trump and that 1990 cover with a less-than-flattering word: embarrassment.
"We don't respect the guy," Cooper Hefner, a self-identified liberal, told the Hollywood Reporter. "There's a personal embarrassment because Trump is somebody who has been on our cover."
The magazine, Cooper Hefner added, is "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."
Detailing his opinions in a series of tweets last month, Cooper Hefner, who has assumed creative control of his father's magazine, said that if the team that made Playboy's editorial decisions had known what Trump would come to embody, "the president would have never found his way onto our cover."
Hefner didn't detail the reasons for his father's changed opinion of Trump.
As Newsweek pointed out, Trump had been a regular at Playboy mansion parties for decades. But as a presidential candidate, Newsweek noted: "Trump pitched himself as a defender of the values of conservative Christians - the very same people Hefner regarded as his chief enemies."
Trump also made same-sex-marriage opponent Mike Pence his running mate and has tried to ban transgender people from serving in the military.
Hefner was a longtime supporter of LGBT rights and took high-profile stands on sodomy laws, same-sex marriage and transgender rights, according to The Washington Post's Derek Hawkins.
Hefner died in his mansion Wednesday of natural causes.
He had started his magazine in 1953 as a counterpoint to culturally conservative times, and the first edition featured a photo of a nude Marilyn Monroe.
As The Post's Matt Schudel wrote: "From the first issue of Playboy in 1953, which featured a photograph of a nude Marilyn Monroe lounging on a red sheet, Mr. Hefner sought to overturn what he considered the puritanical moral code of Middle America. His magazine was shocking at the time, but it quickly found a large and receptive audience and was a principal force behind the sexual revolution of the 1960s."
Excerpts of Alex Haley's "Roots" and Bob Woodward and Carl Bernstein's "All the President's Men" appeared first in Playboy, and Hefner commissioned articles by celebrated writers, including Norman Mailer, James Baldwin and Joyce Carol Oates.
And the magazine offered in-depth interviews with leading political, cultural and business figures - Fidel Castro, Muhammad Ali, Steve Jobs ... and Donald Trump.
In fact, in 1990, Trump the businessman opined on what Trump the president would be like, according to Business Insider:
A president Trump, Donald Trump told Playboy then, "would believe very strongly in extreme military strength. He wouldn't trust anyone. He wouldn't trust the Russians; he wouldn't trust our allies; he'd have a huge military arsenal, perfect it, understand it."
The Atlantic noted in March that after Trump assumed the presidency, some foreign governments turned to that 1990 interview to prepare for White House visits:
"The interview, at turns eerie and prophetic, runs through his typically immodest self-assessment and catalogues his political philosophies, while offering a scathing appraisal of America, which he saw (and still sees) as "weak" and "pushed around" by the rest of the world. In the interview, he also unfurls a blueprint for his hypothetical presidency, years before winning the White House.
"In recent months, at least two world leaders have shared the interview with their staffs in advance of their first meetings with the president. According to the Wall Street Journal, Japanese officials revisited it ahead of Prime Minister Shinzo Abe's visit last month; German Chancellor Angela Merkel also studied it before arriving in the United States this week, several sources say.
"Beyond the standard self-aggrandizement and hagiography of Trump's own business deals, what makes the Playboy interview instructive reading for foreign eyes is how, with greater depth than many of his campaign sound bites, the future president prioritizes America's trade partnerships."
