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Raleigh, N.C., July 5, 2016

Republican presidential candidate Donald Trump signs a copy of Playboy magazine at a campaign rally in Raleigh, N.C., July 5, 2016. (Photo: Joshua Roberts/Reuters)

Hugh Hefner's death recalls one very special Playboy cover

Burt Reynolds, Jerry Seinfeld, Steve Martin, Donald Trump: What do these men have in common?

All of them are among a handful of men who appeared on the cover of Playboy magazine, founded by Hugh Hefner to celebrate the swinging bachelor lifestyle Trump exemplified, before, between, and occasionally during his three marriages.

Hefner died Wednesday at 91.

Trump’s appearance on the cover of the March 1990 issue — he was the subject of the magazine’s signature long-form interview that month — became one of the future president’s treasured mementos. Fans brought them to campaign rallies for Trump to sign. A framed copy occupied a prominent spot on the wall of his Trump Tower office and appeared in the background of photographs of his meeting with evangelical leader Jerry Falwell Jr. last year.

To those who questioned the propriety of his friendship with Trump, Falwell responded that he was “honored for same hypocrites who accused Jesus of being a friend of publicans and sinners to be targeting me over a decades-old mag cover!”

On the cover, Trump, who was 43 at the time, appears in black tie with a saucy photo of model Brandi Brandt, who had been Playboy’s Miss October in 1987. Her subsequent career was less successful than his; the Washington Post reported last year that she was serving a prison sentence for her role in a cocaine-smuggling ring.

In that 1990 interview, Trump showed flashes of the kind of combativeness that would define his presidential candidacy.

“If somebody is trying to do an injustice to me, I fight back harder than anybody I know,” he said. “When somebody tries to harm you or your family, you have an absolute right to fight back.”

Trump also talked about a business trip to Moscow where he said he met with top-level Soviet officials to discuss potential business deals.

“Generally, these guys are much tougher and smarter than our representatives,” Trump said. “We have people in this country just as smart, but unfortunately, they’re not elected officials. … Some of our presidents have been incredible jerk-offs. We need to be tough.”

The interview then turned to Trump’s political ambitions.

“I don’t want the presidency,” Trump said. “If I ever ran for office, I’d do better as a Democrat than as a Republican — and that’s not because I’d be more liberal, because I’m conservative. But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.”

“What’s the first thing President Trump would do upon entering the Oval Office?” the magazine asked.

“Many things,” Trump replied. “A toughness of attitude would prevail.”

He was also asked about the glitz and glamour that had come to define him:

“What does all this — the yacht, the bronze tower, the casinos — really mean to you?”

“Props for the show.”

“And what is the show?”

“The show is ‘Trump,’ and it has sold-out performances everywhere. I’ve had fun doing it and will continue to have fun, and I think most people enjoy it.”

– Jerry Adler and Dylan Stableford

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