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Donald Trump and Hugh Hefner’s Relationship: From Playboy Cover to ‘Personal Embarrassment’

Friendship between publishing giant and now-president soured over time

Donald Trump appeared on the cover of Playboy magazine in 1990, but despite his history with the magazine, the president remained silent when its founder Hugh Hefner passed away on Wednesday, reflecting the downward spiral the pair’s friendship took over the decades.

Trump’s association with the magazine stretched over several years, including the cover shoot alongside Playmate Brandi Brandt and a cameo in an explicit Playboy film in 2001.

But Hefner’s relationship with Trump had reportedly soured, leading Cooper Hefner, his son and successor as leader of Playboy, to denounce the cover in a 2017 interview. He called it a “personal embarrassment” for both the company and his father. “We don’t respect the guy,” he said.

Cooper elaborated further in a series of tweets, writing that Trump’s campaign platform was inconsistent with Playboy’s ideals as a company.

“Why am I embarrassed about this cover? Because we promote a philosophy that encourages ALL individuals to choose the life they want to live,” he wrote. “If the 1990 team at Playboy would have known Trump’s platform than the President would have never found his way onto our cover.”

Hefner first celebrated Trump’s victory over Christian conservative Ted Cruz in a 2015 essay titled “The Conservative Sex Movement,” which has since been taken down. “It’s a sign of the massive changes in the ‘family values party’ and proof of … a sexual revolution in the Republican Party,” he wrote.

No explanation was given for the shift in stance between 2015 and 2017, but as Newsweek pointed out, Trump ended up being a defender of Christian values in the 2016 general election.

“On the campaign trail, Trump pitched himself as a defender of the values of conservative Christians — the very same people Hefner regarded as his chief enemies — and he even spoke at a conference of evangelical leaders in Orlando in August 2016,” Newsweek wrote. “Trump appointed a social conservative who is an opponent of gay marriage, Mike Pence, as his vice president, and Trump’s August ban on transgender people serving in the military earned widespread criticism from LGBT rights groups.”

However, in a tribute to Hefner in the Daily Mail published Thursday, former Playboy editor Heidi Parker wrote that Hefner’s disdain for Trump stretched back as far as 2004. She recalled a demand from the “Celebrity Apprentice” host to appear on the cover again with the female cast of the reality show, to which Hefner responded “Ewww.”

He said “no,” telling Trump that Heidi Parker didn’t like the idea. In response, the now-president demanded the then-editor to be fired. Now, that sounds familiar.

“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,” Parker wrote.