President Trump has some history with the late Hugh Hefner and the Playboy empire he left behind.
During the 2016 election, when Trump’s history with women was being put under a microscope, it was reported that he appeared in a 2000 Playboy softcore porn video in which he pops a bottle of champagne and pours it on the Playboy bunny logo.
Over the years Trump did publicity stunts with Playboy and partied with Hefner and the Playboy playmates.

Donald Trump uses an instant camera to make a picture of Playmate hopeful Lisa Madison during a publicity session in New York, May 3, 1993, where hundreds of women are expected to audition over the next few days in hopes of becoming Playboy’s 40th anniversary Playmate. (AP Photo)
In 2006 he rewarded some contestants on his longtime reality TV show “The Apprentice” with a trip to the Playboy Mansion near Beverly Hills in California.
Trump also was interviewed for Playboy magazine — in which he said, “I hate seeing this country go to hell. We’re laughed at by the rest of the world” — and appeared on the cover of the March 1990 issue standing beside playmate Brandi Brandt.
However, Hefner’s son, Cooper Hefner said in August of 2017 that his father came to view that cover as a mistake.
“We don’t respect the guy,” he told the Hollywood Reporter. “There’s a personal embarrassment because Trump is somebody who has been on our cover.”
Trump had that cover framed and hanging on his New York City office wall as recently as June of last year.
Honored to introduce @realDonaldTrump at religious leader summit in NYC today! He did incredible job! @beckifalwell pic.twitter.com/e2eBSbQwb0
— Jerry Falwell (@JerryFalwellJr) June 21, 2016
Hefner died at the age of 91 on Wednesday, and any statement from the White House regarding the passing of the American icon has yet to be seen.
Presidential administrations do often issue statements when historic figures die, but not always. The Trump White House did so when comedian Jerry Lewis died in August.
