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Playboy founder Hugh Hefner died at the age of of natural causes, the publication announced late Wednesday night.
“Hugh M. Hefner, the American icon who in 1953 introduced the world to Playboy magazine and built the company into one of the most recognizable American global brands in history, peacefully passed away today from natural causes at his home, The Playboy Mansion, surrounded by loved ones,” a statement from Playboy Enterprises to PEOPLE said.
American Icon and Playboy Founder, Hugh M. Hefner passed away today. He was 91. #RIPHef
Hefner was born in Chicago on April 9, 1926 to parents Grace Caroline and Glenn Lucius, both who were both school teachers. He had three wives throughout his life and four children.
Dozens of fans gathered outside of the notorious Playboy Mansion in Beverly Hills after news of Hefner’s death broke.
While Hefner is best known for his time at the Playboy Mansion and as the editor in chief of Playboy, he also immersed himself in charitable work and was also active in politics.
Here’s what you need to know about Hefner’s political stances:
1. Hefner & Trump Had History With Each other
Donald Trump and Hefner have a deep-rooted history together, as the president often did publicity stunts with Playboy. He was often seen partying with playmates and Hefner at the Playboy Mansion years ago.
During the 2016 election, when Trump’s history with women was questioned after a microphone picked up him saying he liked to “grab women by the p***y,” a softcore porn video featuring Trump surfaced where he pops a bottle of champagne and pours it on the Playboy logo, according to Buzzfeed.
Trump’s role in the porn is relatively benign and centers around him breaking a bottle of champagne on a Playboy-branded limo while several of the playmates are visiting New York City. BuzzFeed News obtained the footage from the online-only Buffalo, New York–based video store Cinema Cornucopia.
The softcore film features fully nude women posing in sexual positions, dancing nake and touching themselves while naked.
In 2006, Trump rewarded contestants on his reality TV show “The Apprentice” with a trip to the Playboy Mansion.
2. Trump Was Featured in Playboy Saying He ‘Hated’ Seeing the Country ‘Go to Hell’ & Hefner’s Son Said They Don’t ‘Respect the Guy’
Trump was once interviewed for an article in Playboy where he said he hated “seeing this country go to hell. We’re laughed at by the rest of the world.” He also appeared on the cover of a 1990 issue of the magazine standing next to a playmate.
However, Trump’s son Cooper said in August 2017 that Trump appearing on the cover was viewed as a “mistake” and his father was “embarrassed” that he was on the cover.
“We don’t respect the guy,” Cooper Hefner told the Hollywood Reporter. “There’s a personal embarrassment because Trump is somebody who has been on our cover.”
It’s a cover of Playboy Trump has kept hanging up in his New York City office.
Honored to introduce @realDonaldTrump at religious leader summit in NYC today! He did incredible job! @beckifalwell
3. Hefner Was a Believer in First Amendment Rights & Gave out an Annual Award
GettyHugh Hefner in 2000.
One of the causes Hefner believed in the most was the battle to uphold the First Amendment. His daughter, Christie Hefner, created the Hugh M. Hefner First Amendment Award in 1980 to “honor individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans.”
The award is part of The Playboy Foundation, and over 100 people including high school students, lawyers and journalists have been honored in the over 40 years since its creation.
In 2008, the foundation added the Freedom of Expression Award, which gave a $25,000 cash award to a nominee that’s dedicated to “defending, advocating, or supporting the First Amendment through their personal or professional pursuits.”
4. Hefner Has Donated & Raised Money for the Democratic Party
GettyPlayboy Magazine owner Hugh Hefner and Crystal Harris arrives at the TCM Classic Film Festival’s gala opening night world premiere of the newly restored film “A Star Is Born” at Grauman’s Chinese Theatre on April 22, 2010 in Hollywood, California.
According to records of his political campaign contributions include many large sums to the Democratic Party. In 2011, though, he referred to himself as an independent because of “disillusionment” within both the Democratic and Republican parties.
Hefner tweeted that his parents were both Republicans and he’s a registered Democrat.
@Politicalish My parents were Republican, I’m a registered Democrat, but these days I’m an Independent, not happy with either Party.
In 2012, Hefner supported President Barack Obama‘s reelection effort. He said on Twitter that he was “playing dominoes with the girls” when he go the news that Obama was reelected and they “celebrated” afterward.
While I was playing dominoes with the girls, we got the news that Obama had been re-elected. We’re celebrating at the Mansion.
5. Hefner Supported Same-Sex Marriage & Also Donated Funds to Create a Censorship Class at USC
GettyHugh Hefner and his former wife Kimberley Conrad Hefner who both accepted Wildlife achievement awards at the 9th annual “Safari Brunch” at the Playboy Mansion to benefit the Wildlife Waystation, Country’s Premier wild Animal Refuge October 18, 2003 in Bel Air, California.
Hefner was a known supporter for same-sex marriage and said the fight to maintain it was “a fight or all our rights. Without it, we will turn back the sexual revolution and return to an earlier, puritanical time.”
Hefner wrote about his views on the subject in a letter titled “Sexual Freedom” in the September 2012 issue of Playboy.
Today, in every instance of sexual rights falling under attack, you’ll find legislation forced into place by people who practice discrimination disguised as religious freedom. Their goal is to dehumanize everyone’s sexuality and reduce us to using sex for the sole purpose of perpetuating our species. To that end, they will criminalize your entire sex life.
In 2007, Hefner announced he was contributing to the University of Southern California’s School of Cinematic Arts so it could create a course called “Censorship in Cinema,” USA Today reported. The donation was $100,000, and he also put forth $2 million to endow a chair for the study of American film.