Hugh Hefner’s death at 91 has already spurred countless debates about his complicated legacy. Was he a champion for women or a champion for men’s ability to use and discard women? Was he a pioneer or a relic? But there’s one thing he clearly was: a man who lived a lifestyle that nobody else, not even Donald Trump, could quite pull off.

For decades, columnists have lumped now-president Trump and the late Playboy founder into the same category. Some of that was for good reason; they both hit their gossip-fodder heydays in the 1980’s. Then, Hef’s advancing age turned his public displays of virility into an eyebrow-raising circus until he slowed down and married. At the same time, Donald Trump, flashy totem of consumption, really hit his model-hopping stride.

But what Hefner did, Trump did later, sloppier. He was always a few steps behind and, somehow, less cool.

Playboy was founded in 1953, and partially funded by a $1,000 loan from Hefner’s mother. At its peak, November 1972, more than 7 million copies were sold. The magazine currently has a circulation of 673,000 (full disclosure: I’ve written for Playboy magazine, in March-April 2016, the first episode that didn’t feature nudity. They’ve since gone back to featuring nudity). Trump got his jump-start in business thanks to a multi-million dollar loan from his father. His first magazine, Trump Style, was launched in 1997 as a giveaway to guests at Trump-branded properties. That magazine was later rebranded Trump World, and then relaunched again as Trump magazine. That quickly folded.

Hugh Hefner bought an airplane and turned it into a flying pleasure palace in the 1970’s. He called the 727 “Big Bunny.” Trump did it the next decade, but with more gold and without a cute name. Atlantic City hosted a Playboy-branded casino before it hosted one with Trump’s name on it.

For Playboy’s 35th anniversary party in 1988, Hugh Hefner stayed home in his mansion with his new wife and drank Diet Pepsi. Donald Trump was there with his first wife Ivana, gauchely causing a bigger stir than the year’s Playmate of the Year. A Chicago Tribune writeup of the party noted that he was “riding high on the news that Soviet General Secretary Mikhail Gorbachev is expected to visit Trump Tower’s posh shops and condos this week.” One of the precious few times Donald Trump has willingly admitted to having contact with a Russian.

After the 2004 Super Bowl, Hugh Hefner had Tom Brady over to his house. Donald Trump tried to set him up with his daughter Ivanka.

Trump even romantically pursued Hefner’s ex-wife Kimberley. When Hefner and his then-wife’s marriage hit the rocks in 1998, so much gossip was printed about her alleged dalliances with Trump that Kimberley felt the need to clarify that she was not dating him. She told Esquire’s Billy Zehme, “I know exactly what the Donald is about!... I would really appreciate it if you could get it in somewhere that I am definitely not in love with the Donald.” The Esquire profile noted that Trump “smelled blood in the water” and “started calling her from the moment the [Hefners’] separation news hit in January.” The pair had since reconciled. A New York Daily News column at the time cited a “source at Trump Tower” that countered that Kimberley was still “very friendly” with Trump, and that she’d already left him three messages at his office that day. Wonder who that could have been!

In 2001, Hefner was roasted by the New York Friars Club, laughing along with the jokes about his age, sexuality, the seven blonde girlfriends he brought with him to the event. Comedian Jeff Ross ended his roast of the mogul by saying, “I think you’re the coolest guy in the world.” and shaking his hand.

Three years later, in 2004, it was Donald Trump’s turn in the roasting chair. He handled it just fine. He did it again, for Comedy Central, in 2011, an event he handled so poorly that it’s become sort of legendary. Before the roast, he demanded no jokes be made about his not being as wealthy as he said he was. His assistant let participants know that they were to address him as “Mr. Trump.” He was slated to arrive in a golf cart flanked by beautiful women, but decided that one of the models wasn’t hot enough for him, so she had to stand on the other side of the stage. Writers of the roast sent him a draft of his “rebuttal,” a chance to counter-roast the roasters, and the future president sent the draft back with black sharpie blacking out some of the jokes’ punch lines. The most cringe-inducing part of the event was the quick cut to Ivanka laughing her face off after Snoop Dogg said Trump should go ahead and run for President because it wouldn’t be the first time he kicked a black family out of their home.

Trump frequented the Playboy mansion. He partied there, hung out there, flirted with the women there. Trump took the winners of a challenge on 'The Apprentice' to the Playboy Mansion in 2006, where several of the Playmates surprised the contestants with a pool party. One contestant recounted to Newsweek that at one point in the party, “Trump looked at Hefner and said, ‘It’s hard for me to tell which of these girls are yours and which ones are mine.’”

Trump appeared on the cover of Playboy in 1990, one of seven men to ever grace the cover. In 2015, Hefner wrote an essay about how Trump’s Republican primary victories were a harbinger of a GOP “sexual revolution.” But in August 2016, Hef’s son Cooper called the cover, which hangs in a place of pride in Trump Tower, a source of “personal embarrassment.” The praising essay can no longer be found on Playboy’s website. It seems in the last months of Hefner’s life, the first months of Trump’s presidency, the two men did not speak much.

Both men have troubling legacies; both had tacky aesthetics and pushed a manicured, waxed, bleached, and tanned feminine ideal, the sort of ideal that doesn’t leave much space for a woman to be human. For that reason, Hefner should occupy a place in pop culture purgatory as critics and historians debate whether or not he was a net force for good or bad.

But Hefner fought for sexual liberation for his entire career. He supported abortion access before abortion was legal, birth control access, he stood up for gay rights, he spoke with compassion and sanity about the AIDS crisis as it unfolded. Trump, at one point in his life, said he believed in abortion, but given the benefit of hindsight (he’s now against choice) it seems that he only wanted women to be free to have abortions inasmuch as it gave him access to consequence-free sex, and only stands against it inasmuch as it gives him access to Mike Pence. While Hefner’s critics point out that his feminist-leaning advocacy could easily be seen as a means to his hedonistic ends, there’s little doubt what Trump’s was. And there’s little doubt what Trump will never be.