How Trump’s Playboy Persona Came Back to Haunt Him

The particulars of the indictment against former President Donald J. Trump have yet to be revealed, but the salient details are heaven-made for headlines and screen crawls:

Sex. Porn star. Sex. Hush money. Sex.

Mr. Trump maintains his innocence in now-familiar fashion, framing himself as the righteous victim of “thugs and radical left monsters.” But the indictment’s salacious nature resurrects the Donald Trump who existed well before he became the 45th president — before his ubiquitous MAGA catchphrase, before his claims to be greater than Washington or Lincoln, before the two impeachments and one Capitol riot.

That would be the Donald Trump who liked to present himself as a player, extremely confident that his wealth and looks made him catnip to women. A man who could talk about threesomes with a radio shock jock, boldly stroll through a dressing area filled with pageant contestants, rate women on a 1-to-10 scale based on their physical appearance.

It is a part of Mr. Trump’s persona that has repeatedly come back to haunt him, most recently on Thursday, when a Manhattan grand jury forever branded him as the first former president formally charged with a crime.

The little known about the case is scandalous enough. It revolves around $130,000 that Mr. Trump’s personal lawyer, Michael D. Cohen, paid to the pornographic film actress Stormy Daniels for her silence about an alleged sexual encounter with Mr. Trump in 2006, well before his presidency and while his third wife stayed home with their infant son.

Mr. Trump, who recently began his campaign for the 2024 presidential election, is hardly the first president to be linked to sexual impropriety. Bill Clinton had sexual relations with the female intern he infamously said he didn’t have sexual relations with — in the Oval Office. John F. Kennedy’s many affairs included one with a woman who was also intimate with a Chicago mob boss. Warren G. Harding fathered a child with a mistress who claimed that they had sex in a White House coat room. There are more.

But Mr. Trump’s long public history of entanglements, boasts and crude comments distinguishes him in the presidential pantheon.

As a young man in the 1970s, Mr. Trump hit the Manhattan clubs and tipped off the gossip columns to his dalliances, all in keeping with his effort to shed the appearance of being just a rich kid from Queens working for his father’s real estate company.

He married Ivana Zelnickova, a Czech model, in 1977 and concentrated on making his mark in high-stakes real estate. But their relationship foundered in 1989 when Ms. Trump discovered what others already knew: that Mr. Trump was having an affair with a model and actress named Marla Maples.

The tit-for-tat squabbling that ensued was the tabloid gift that kept on giving, with a highlight — or lowlight — being a New York Post front page in 1990 that featured a grinning Mr. Trump and a headline that said: “Marla boasts to her pals about Donald: ‘BEST SEX I’VE EVER HAD.’”

Lou Colasuonno, the Post editor who laid out that front page, remembered thinking, “He’s never going to sue us for this headline.”

The circumstances behind the headline are part of conflicting newspaper lore. But Ms. Maples, whose marriage to Mr. Trump ended in 1999, subsequently denied saying those words, and Barbara Res, a former Trump Organization executive, later said that while she worried about its impact on the Trump children, their father “thought it was the greatest thing.”

The perception of sexual prowess seemed central to the persona that Mr. Trump cultivated.

Linda Stasi, a novelist and former columnist for both The Post and The Daily News, recalled in an email that Mr. Trump once left a message on her voice mail, pretending to be someone else — as he often did — and saying in a fake voice that Donald Trump was having lunch at such-and-such restaurant and was surrounded by beautiful models.

“You should write about this,” she recalled the tipster saying.

“His fake accent was about as real as his orange tan,” wrote Ms. Stasi, who added that the first time she met Mr. Trump, he said, “Well, you’re a pretty one, aren’t you?”

“I think I said, ‘What? Seriously?’”

And Mr. Colasuonno, a former editor-in-chief for both The Post and The Daily News, remembered sharing two private meals with Mr. Trump in the early 1990s, at a time when the real estate developer was frantically denying his very obvious and deep financial troubles.

“The conversation was 50 percent about ‘babes’ — he’d use that archaic term — and the other half were lies about his financial situation,” Mr. Colasuonno said.

At times it seemed that Mr. Trump judged the world based on some frat-boy ranking system of hotness. While serving as the editor of Vanity Fair in 1993, Graydon Carter invited Mr. Trump to be a guest of the magazine at the White House Correspondents’ dinner. Mr. Carter said he seated the developer beside a well-known model, who before long asked to move to another seat. “He is the most vulgar human being I have ever met,” he recalled her saying. “He asked me to judge whether other women’s legs and breasts are better or inferior to his wife’s.”

The seating was rearranged, Mr. Carter said in an interview. “She was angry.”

Another woman, the journalist E. Jean Carroll, has alleged that around this time — in 1995 or 1996 — she encountered Mr. Trump, an acquaintance, in a high-end Manhattan department store. After he asked for help in buying a gift for a woman, she said, the two wound up in a dressing room, where he raped her.

Ms. Carroll laid out her allegations in a New York magazine article in 2019. Mr. Trump denied the charges this way: “I’ll say it with great respect: No. 1, she’s not my type. No. 2, it never happened. It never happened, OK?”

Ms. Carroll has since filed two civil lawsuits against Mr. Trump, for defamation and for battery and defamation. One of those cases is set to go to trial this month.

Mr. Trump did not reserve his crass comments for private conversations, as evidenced by his many appearances on the Howard Stern radio show. In bantering with its provocative host from 2005 to 2010, for example, the future president rated women on their looks — Tiger Woods’s then wife Elin Nordegren was “a solid 9” — suggested that he had once had a threesome with women whose combined weight was 375 pounds, and recalled a particular perk of owning the Miss Universe pageant: going backstage for a so-called inspection while contestants were dressing.

“They’re standing there with no clothes,” he said, as CNN reported in 2016. “‘Is everybody OK?’ And you see these incredible looking women, and so I sort of get away with things like that.”

Mr. Trump’s documented penchant for misogynistic behavior was no secret to the electorate as he ran for the presidency in 2016.

A month before the November election, The Washington Post published a 2005 video of Mr. Trump, then 59, talking about women with the television personality Billy Bush as they prepared for an episode of the “Access Hollywood” program. The transcript of their conversation reads like an unfunny script from a rejected “Animal House” sequel.

Some of Mr. Trump’s recorded comments, peppered with crude references to the female anatomy, are more famous than most of his speeches as president. “Just kiss,” he advised at one point. “I don’t even wait. And when you’re a star, they let you do it. You can do anything.”

After initially playing down his comments as “locker-room banter,” Mr. Trump apologized to his family and to the American people. Within a few weeks he won the presidency; within a few months, he privately began questioning the tape’s authenticity.

But Mr. Trump’s past as a self-styled player kept bobbing to the surface of the MAGA-red sea.

In early 2018, The Wall Street Journal broke the story about the $130,000 that Mr. Trump’s personal lawyer, Mr. Cohen, personally paid to Ms. Daniels to buy her silence about her alleged one-night stand with Mr. Trump after a charity golf event 12 years earlier.

Mr. Cohen was later convicted of tax fraud and campaign finance violations after admitting that he had provided hush money to Ms. Daniels and helped to arrange a similar payment to another woman, a Playboy model named Karen McDougal. He did so, he has said, at the direction of Mr. Trump, who denies this.

Mr. Trump has also denied having sex with Ms. Daniels and has taken to calling her “Horseface.” She has responded by referring to the “shortcomings” of the 45th president.